You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (20)transporters (1) Show 21 proteins XML

enzymes (20)transporters (1) Show 21 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015331

Secondary Accession Numbers

HMDB15331

Metabolite Identification

Common Name

Bromocriptine

Description

Bromocriptine, also known as parlodel, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Bromocriptine is a drug which is used for the treatment of galactorrhea due to hyperprolactinemia, prolactin-dependent menstrual disorders and infertility, prolactin-secreting adenomas, prolactin-dependent male hypogonadism, as adjunct therapy to surgery or radiotherapy for acromegaly or as monotherapy is special cases, as monotherapy in early parksinsonian syndrome or as an adjunct with levodopa in advanced cases with motor complications. bromocriptine has also been used off-label to treat restless legs syndrome and neuroleptic malignant syndrome. Bromocriptine is a very strong basic compound (based on its pKa). Bromocriptine use has been anecdotally associated with causing or worsening psychotic symptoms (its mechanism is in opposition of most antipsychotics, whose mechanisms generally block dopamine receptors). Bromocriptine is a potentially toxic compound. Bromocriptine is a semisynthetic derivative of a natural ergot alkaloid, ergocryptine (a derivative of lysergic acid), which is synthesized by bromination of ergocryptine using N-bromosuccinimide. Since the late 1980s it has been used, off-label, to reduce the symptoms of cocaine withdrawal but the evidence for this use is poor. It is a bile salt export pump inhibitor. As of July 2017, bromocriptine was marketed under many brand names worldwide, including Abergin, Barlolin, Brameston, Brocriptin, Brom, Broma-Del, Bromergocryptine, Bromergon, Bromicon, Bromocorn, Bromocriptin, Bromocriptina, Bromocriptine, Bromocriptine mesilate, Bromocriptine mesylate, Bromocriptine methanesulfonate, Bromocriptini mesilas, Bromocriptinmesilat, Bromodel, Bromokriptin, Bromolac, Bromotine, Bromtine, Brotin, Butin, Corpadel, Cripsa, Criptine, Criten, Cycloset, Degala, Demil, Deparo, Deprolac, Diacriptin, Dopagon, Erenant, Grifocriptina, Gynodel, kirim, Kriptonal, Lactodel, Medocriptine, Melen, Padoparine, Palolactin, Parlodel, Pravidel, Proctinal, Ronalin, Semi-Brom, Serocriptin, Serocryptin, Suplac, Syntocriptine, Umprel, Unew, Updopa, Upnol B, and Volbro. Bromocriptine is a potent agonist at dopamine D2 receptors and various serotonin receptors. Bromocriptine (originally marketed as Parlodel, subsequently under many names) is an ergoline derivative and dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease (PD), hyperprolactinaemia, neuroleptic malignant syndrome, and type 2 diabetes. Most frequent side effects are nausea, orthostatic hypotension, headaches, and vomiting through stimulation of the brainstem vomiting centre.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1200
  Mrv0541 02231215192D          

 45 51  0  0  1  0            999 V2000
    7.7908   -3.2238    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    1.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504    2.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5180    1.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183    4.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    2.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    3.9255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698    0.4937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742   -0.7468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493   -4.1429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    3.2562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7712    2.5038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0744    3.0900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6525    3.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0546    1.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4288    4.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7636    1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    3.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049    0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776    3.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629   -0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -0.7411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6609   -1.6061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9333   -0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1984    3.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391    4.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465   -2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3755   -2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3755   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6609   -3.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3934   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742   -4.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9835   -3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -3.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9333   -4.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -4.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    2.7645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2350   -1.2805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 40  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
 13  3  1  6  0  0  0
  4 19  2  0  0  0  0
  5 20  2  0  0  0  0
  6 26  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 19  1  0  0  0  0
  8 12  1  0  0  0  0
  8 17  1  0  0  0  0
  8 20  1  0  0  0  0
 16  9  1  6  0  0  0
  9 26  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 12 44  1  1  0  0  0
 14 20  1  0  0  0  0
 14 21  1  6  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 30  1  0  0  0  0
 23 31  1  0  0  0  0
 27 26  1  1  0  0  0
 27 29  1  0  0  0  0
 27 33  1  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
 28 45  1  1  0  0  0
 32 33  2  0  0  0  0
 32 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  2  0  0  0  0
 35 41  1  0  0  0  0
 36 37  1  0  0  0  0
 36 40  2  0  0  0  0
 37 39  1  0  0  0  0
 39 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END

HMDB0015331
     RDKit          3D
Bromocriptine
 83 89  0  0  0  0  0  0  0  0999 V2000
   -4.1963    3.5565    1.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    3.2632    0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    4.4832   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.0334    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185    0.7854    0.3988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2567    0.4861   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2114    1.2973   -0.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943   -0.6772   -1.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906   -0.9804   -2.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029   -2.4659   -3.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213   -2.5986   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -1.7821   -0.9874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0782   -1.2418   -0.3427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3602   -0.5941   -1.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -2.2417    0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.8516    1.4575 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4327   -1.2518    1.4150 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.7232    2.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192   -0.7885    3.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -0.1034    2.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6128    1.0621    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    0.9006    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    2.0761   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513    3.2357   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    4.2485   -1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    4.1143   -2.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631    2.9252   -2.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    2.4518   -2.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8944    1.1653   -2.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2022    0.0368   -3.3946 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    0.8493   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.9561   -1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -0.3745   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -0.3985   -0.0298 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3572   -1.4409    0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -2.6815    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516   -1.1080    2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089   -3.0618    2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135   -4.1428    1.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -3.6498    2.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -0.8185    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075   -0.4071    3.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -0.3427    0.7063 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    2.7514    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8381    4.4312    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    3.8617    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    3.2698   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    5.3950    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    4.3399    0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    4.7061   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    2.1815    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285    1.9098   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    0.9728    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6676   -0.7710   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -0.4364   -3.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1233   -3.0243   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1633   -2.7052   -4.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -2.0849   -2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -3.6413   -1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706   -2.3357   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.1812   -1.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066   -1.2238    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    0.3007    3.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    2.0727    2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    3.3698    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670    5.2151   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    4.9091   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918    2.9591   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600   -1.2329   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7496   -0.5082    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937   -0.5861   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447   -2.5136    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394   -3.1170   -0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -3.4182    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629   -0.7477    2.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1876   -2.0438    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.8446    3.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -4.5745    2.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114   -3.6694    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794   -4.9666    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520   -3.0072    3.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -4.7101    2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8686   -3.5028    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 16 38  1  0
 38 39  1  0
 38 40  1  0
 16 41  1  0
 41 42  2  0
 41 43  1  0
 43  5  1  0
 12  8  1  0
 43 13  1  0
 37 20  1  0
 34 22  1  0
 32 23  1  0
 32 27  2  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  1
  9 54  1  0
  9 55  1  0
 10 56  1  0
 10 57  1  0
 11 58  1  0
 11 59  1  0
 12 60  1  1
 14 61  1  0
 17 62  1  0
 20 63  1  1
 21 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 28 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  6
 36 72  1  0
 36 73  1  0
 36 74  1  0
 37 75  1  0
 37 76  1  0
 38 77  1  0
 39 78  1  0
 39 79  1  0
 39 80  1  0
 40 81  1  0
 40 82  1  0
 40 83  1  0
M  END

1200
  Mrv0541 02231215192D          

 45 51  0  0  1  0            999 V2000
    7.7908   -3.2238    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    1.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504    2.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5180    1.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183    4.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    2.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    3.9255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698    0.4937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742   -0.7468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493   -4.1429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    3.2562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7712    2.5038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0744    3.0900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6525    3.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0546    1.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4288    4.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7636    1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    3.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049    0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776    3.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629   -0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -0.7411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6609   -1.6061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9333   -0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1984    3.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391    4.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465   -2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3755   -2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3755   -2.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6609   -3.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3934   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742   -4.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9835   -3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -3.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9333   -4.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -4.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    2.7645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2350   -1.2805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 40  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
 13  3  1  6  0  0  0
  4 19  2  0  0  0  0
  5 20  2  0  0  0  0
  6 26  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 19  1  0  0  0  0
  8 12  1  0  0  0  0
  8 17  1  0  0  0  0
  8 20  1  0  0  0  0
 16  9  1  6  0  0  0
  9 26  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 12 44  1  1  0  0  0
 14 20  1  0  0  0  0
 14 21  1  6  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 30  1  0  0  0  0
 23 31  1  0  0  0  0
 27 26  1  1  0  0  0
 27 29  1  0  0  0  0
 27 33  1  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
 28 45  1  1  0  0  0
 32 33  2  0  0  0  0
 32 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  2  0  0  0  0
 35 41  1  0  0  0  0
 36 37  1  0  0  0  0
 36 40  2  0  0  0  0
 37 39  1  0  0  0  0
 39 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015331

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1

> <INCHI_KEY>
OZVBMTJYIDMWIL-AYFBDAFISA-N

> <FORMULA>
C32H40BrN5O5

> <MOLECULAR_WEIGHT>
654.595

> <EXACT_MASS>
653.221282062

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
66.43538723439508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.8871678083333325

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.12967619452806

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.677615603064185

> <JCHEM_PKA_STRONGEST_BASIC>
6.713916261746808

> <JCHEM_POLAR_SURFACE_AREA>
118.20999999999998

> <JCHEM_REFRACTIVITY>
165.51239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromocriptine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015331
     RDKit          3D
Bromocriptine
 83 89  0  0  0  0  0  0  0  0999 V2000
   -4.1963    3.5565    1.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    3.2632    0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    4.4832   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.0334    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185    0.7854    0.3988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2567    0.4861   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2114    1.2973   -0.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943   -0.6772   -1.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906   -0.9804   -2.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029   -2.4659   -3.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213   -2.5986   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -1.7821   -0.9874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0782   -1.2418   -0.3427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3602   -0.5941   -1.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -2.2417    0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.8516    1.4575 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4327   -1.2518    1.4150 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.7232    2.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192   -0.7885    3.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -0.1034    2.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6128    1.0621    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    0.9006    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    2.0761   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513    3.2357   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    4.2485   -1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    4.1143   -2.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631    2.9252   -2.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    2.4518   -2.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8944    1.1653   -2.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2022    0.0368   -3.3946 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    0.8493   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.9561   -1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -0.3745   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -0.3985   -0.0298 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3572   -1.4409    0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -2.6815    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516   -1.1080    2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089   -3.0618    2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135   -4.1428    1.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -3.6498    2.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -0.8185    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075   -0.4071    3.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -0.3427    0.7063 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    2.7514    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8381    4.4312    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    3.8617    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    3.2698   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    5.3950    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    4.3399    0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    4.7061   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    2.1815    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285    1.9098   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    0.9728    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6676   -0.7710   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -0.4364   -3.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1233   -3.0243   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1633   -2.7052   -4.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -2.0849   -2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -3.6413   -1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706   -2.3357   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.1812   -1.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066   -1.2238    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    0.3007    3.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    2.0727    2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    3.3698    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670    5.2151   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    4.9091   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918    2.9591   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600   -1.2329   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7496   -0.5082    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937   -0.5861   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447   -2.5136    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394   -3.1170   -0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -3.4182    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629   -0.7477    2.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1876   -2.0438    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.8446    3.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -4.5745    2.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114   -3.6694    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794   -4.9666    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520   -3.0072    3.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -4.7101    2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8686   -3.5028    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 16 38  1  0
 38 39  1  0
 38 40  1  0
 16 41  1  0
 41 42  2  0
 41 43  1  0
 43  5  1  0
 12  8  1  0
 43 13  1  0
 37 20  1  0
 34 22  1  0
 32 23  1  0
 32 27  2  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  1
  9 54  1  0
  9 55  1  0
 10 56  1  0
 10 57  1  0
 11 58  1  0
 11 59  1  0
 12 60  1  1
 14 61  1  0
 17 62  1  0
 20 63  1  1
 21 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 28 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  6
 36 72  1  0
 36 73  1  0
 36 74  1  0
 37 75  1  0
 37 76  1  0
 38 77  1  0
 39 78  1  0
 39 79  1  0
 39 80  1  0
 40 81  1  0
 40 82  1  0
 40 83  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1200                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0      14.543  -6.018   0.000  0.00  0.00          Br+0
HETATM    2  O   UNK     0       4.559   3.271   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.641   4.829   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.434   2.398   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.874   8.422   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.152  -1.394   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.705   4.519   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.442   7.328   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.477   0.922   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      10.592  -1.394   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      12.412  -7.733   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.541   6.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.173   4.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.606   5.768   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.085   6.549   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.702   2.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.534   8.560   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   8.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.025   3.022   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.974   7.172   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.138   5.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.676   1.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.038   6.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.157  -0.359   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.168   1.418   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.483  -0.618   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.820  -1.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.567  -2.998   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.209  -0.581   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.570   6.707   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.406   8.267   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.233  -3.768   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.832  -2.987   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.901  -3.768   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.233  -5.308   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.901  -5.308   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.567  -6.078   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.934  -0.640   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.592  -7.682   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.036  -6.335   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.832  -6.089   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.209  -8.495   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.820  -7.693   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0       3.719   5.160   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      11.639  -2.390   0.000  0.00  0.00           H+0
CONECT    1   40                                                            
CONECT    2   13   16                                                       
CONECT    3   13                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6   26                                                            
CONECT    7   13   14   19                                                  
CONECT    8   12   17   20                                                  
CONECT    9   16   26                                                       
CONECT   10   28   29   38                                                  
CONECT   11   39   40                                                       
CONECT   12    8   13   15   44                                             
CONECT   13    2    3    7   12                                             
CONECT   14    7   20   21                                                  
CONECT   15   12   18                                                       
CONECT   16    2    9   19   22                                             
CONECT   17    8   18                                                       
CONECT   18   15   17                                                       
CONECT   19    4    7   16                                                  
CONECT   20    5    8   14                                                  
CONECT   21   14   23                                                       
CONECT   22   16   24   25                                                  
CONECT   23   21   30   31                                                  
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    6    9   27                                                  
CONECT   27   26   29   33                                                  
CONECT   28   10   32   34   45                                             
CONECT   29   10   27                                                       
CONECT   30   23                                                            
CONECT   31   23                                                            
CONECT   32   28   33   35                                                  
CONECT   33   27   32                                                       
CONECT   34   28   36                                                       
CONECT   35   32   37   41                                                  
CONECT   36   34   37   40                                                  
CONECT   37   35   36   39                                                  
CONECT   38   10                                                            
CONECT   39   11   37   42                                                  
CONECT   40    1   11   36                                                  
CONECT   41   35   43                                                       
CONECT   42   39   43                                                       
CONECT   43   41   42                                                       
CONECT   44   12                                                            
CONECT   45   28                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

COMPND    HMDB0015331
HETATM    1  C1  UNL     1      -4.196   3.557   1.216  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.340   3.263   0.000  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.427   4.483  -0.163  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.508   2.033   0.161  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.319   0.785   0.399  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.257   0.486  -0.710  1.00  0.00           C  
HETATM    7  O1  UNL     1      -5.211   1.297  -0.926  1.00  0.00           O  
HETATM    8  N1  UNL     1      -4.094  -0.677  -1.512  1.00  0.00           N  
HETATM    9  C7  UNL     1      -4.591  -0.980  -2.840  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.303  -2.466  -3.018  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.021  -2.599  -2.222  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.329  -1.782  -0.987  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.078  -1.242  -0.343  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.360  -0.594  -1.358  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.298  -2.242   0.207  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.885  -1.852   1.457  1.00  0.00           C  
HETATM   17  N2  UNL     1       0.433  -1.252   1.415  1.00  0.00           N  
HETATM   18  C13 UNL     1       1.070  -0.723   2.545  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.419  -0.788   3.658  1.00  0.00           O  
HETATM   20  C14 UNL     1       2.379  -0.103   2.644  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.613   1.062   1.740  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.150   0.901   0.552  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.375   2.076  -0.327  1.00  0.00           C  
HETATM   24  C18 UNL     1       2.651   3.236  -0.160  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.963   4.248  -1.045  1.00  0.00           C  
HETATM   26  C20 UNL     1       3.945   4.114  -2.047  1.00  0.00           C  
HETATM   27  C21 UNL     1       4.663   2.925  -2.192  1.00  0.00           C  
HETATM   28  N3  UNL     1       5.637   2.452  -2.996  1.00  0.00           N  
HETATM   29  C22 UNL     1       5.894   1.165  -2.581  1.00  0.00           C  
HETATM   30 BR1  UNL     1       7.202   0.037  -3.395  1.00  0.00          BR  
HETATM   31  C23 UNL     1       5.084   0.849  -1.528  1.00  0.00           C  
HETATM   32  C24 UNL     1       4.320   1.956  -1.295  1.00  0.00           C  
HETATM   33  C25 UNL     1       4.926  -0.375  -0.695  1.00  0.00           C  
HETATM   34  C26 UNL     1       3.564  -0.398  -0.030  1.00  0.00           C  
HETATM   35  N4  UNL     1       3.357  -1.441   0.908  1.00  0.00           N  
HETATM   36  C27 UNL     1       4.015  -2.681   0.556  1.00  0.00           C  
HETATM   37  C28 UNL     1       3.452  -1.108   2.293  1.00  0.00           C  
HETATM   38  C29 UNL     1      -0.909  -3.062   2.367  1.00  0.00           C  
HETATM   39  C30 UNL     1       0.013  -4.143   1.851  1.00  0.00           C  
HETATM   40  C31 UNL     1      -2.304  -3.650   2.457  1.00  0.00           C  
HETATM   41  C32 UNL     1      -1.845  -0.819   1.893  1.00  0.00           C  
HETATM   42  O5  UNL     1      -2.107  -0.407   3.034  1.00  0.00           O  
HETATM   43  N5  UNL     1      -2.461  -0.343   0.706  1.00  0.00           N  
HETATM   44  H1  UNL     1      -4.877   2.751   1.491  1.00  0.00           H  
HETATM   45  H2  UNL     1      -4.838   4.431   0.930  1.00  0.00           H  
HETATM   46  H3  UNL     1      -3.598   3.862   2.083  1.00  0.00           H  
HETATM   47  H4  UNL     1      -3.995   3.270  -0.881  1.00  0.00           H  
HETATM   48  H5  UNL     1      -2.906   5.395   0.269  1.00  0.00           H  
HETATM   49  H6  UNL     1      -1.481   4.340   0.387  1.00  0.00           H  
HETATM   50  H7  UNL     1      -2.241   4.706  -1.234  1.00  0.00           H  
HETATM   51  H8  UNL     1      -1.746   2.182   0.950  1.00  0.00           H  
HETATM   52  H9  UNL     1      -1.928   1.910  -0.790  1.00  0.00           H  
HETATM   53  H10 UNL     1      -3.896   0.973   1.352  1.00  0.00           H  
HETATM   54  H11 UNL     1      -5.668  -0.771  -2.861  1.00  0.00           H  
HETATM   55  H12 UNL     1      -4.077  -0.436  -3.633  1.00  0.00           H  
HETATM   56  H13 UNL     1      -5.123  -3.024  -2.554  1.00  0.00           H  
HETATM   57  H14 UNL     1      -4.163  -2.705  -4.089  1.00  0.00           H  
HETATM   58  H15 UNL     1      -2.206  -2.085  -2.773  1.00  0.00           H  
HETATM   59  H16 UNL     1      -2.806  -3.641  -1.995  1.00  0.00           H  
HETATM   60  H17 UNL     1      -3.971  -2.336  -0.281  1.00  0.00           H  
HETATM   61  H18 UNL     1      -1.977  -0.181  -1.997  1.00  0.00           H  
HETATM   62  H19 UNL     1       0.907  -1.224   0.492  1.00  0.00           H  
HETATM   63  H20 UNL     1       2.578   0.301   3.683  1.00  0.00           H  
HETATM   64  H21 UNL     1       2.349   2.073   2.040  1.00  0.00           H  
HETATM   65  H22 UNL     1       1.906   3.370   0.585  1.00  0.00           H  
HETATM   66  H23 UNL     1       2.467   5.215  -1.025  1.00  0.00           H  
HETATM   67  H24 UNL     1       4.183   4.909  -2.737  1.00  0.00           H  
HETATM   68  H25 UNL     1       6.092   2.959  -3.765  1.00  0.00           H  
HETATM   69  H26 UNL     1       4.960  -1.233  -1.395  1.00  0.00           H  
HETATM   70  H27 UNL     1       5.750  -0.508   0.032  1.00  0.00           H  
HETATM   71  H28 UNL     1       2.794  -0.586  -0.857  1.00  0.00           H  
HETATM   72  H29 UNL     1       5.045  -2.514   0.193  1.00  0.00           H  
HETATM   73  H30 UNL     1       3.439  -3.117  -0.298  1.00  0.00           H  
HETATM   74  H31 UNL     1       3.982  -3.418   1.374  1.00  0.00           H  
HETATM   75  H32 UNL     1       4.463  -0.748   2.590  1.00  0.00           H  
HETATM   76  H33 UNL     1       3.188  -2.044   2.860  1.00  0.00           H  
HETATM   77  H34 UNL     1      -0.607  -2.845   3.409  1.00  0.00           H  
HETATM   78  H35 UNL     1       0.640  -4.574   2.686  1.00  0.00           H  
HETATM   79  H36 UNL     1       0.711  -3.669   1.154  1.00  0.00           H  
HETATM   80  H37 UNL     1      -0.579  -4.967   1.401  1.00  0.00           H  
HETATM   81  H38 UNL     1      -2.852  -3.007   3.201  1.00  0.00           H  
HETATM   82  H39 UNL     1      -2.329  -4.710   2.701  1.00  0.00           H  
HETATM   83  H40 UNL     1      -2.869  -3.503   1.506  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3    4   47
CONECT    3   48   49   50
CONECT    4    5   51   52
CONECT    5    6   43   53
CONECT    6    7    7    8
CONECT    8    9   12
CONECT    9   10   54   55
CONECT   10   11   56   57
CONECT   11   12   58   59
CONECT   12   13   60
CONECT   13   14   15   43
CONECT   14   61
CONECT   15   16
CONECT   16   17   38   41
CONECT   17   18   62
CONECT   18   19   19   20
CONECT   20   21   37   63
CONECT   21   22   22   64
CONECT   22   23   34
CONECT   23   24   24   32
CONECT   24   25   65
CONECT   25   26   26   66
CONECT   26   27   67
CONECT   27   28   32   32
CONECT   28   29   68
CONECT   29   30   31   31
CONECT   31   32   33
CONECT   33   34   69   70
CONECT   34   35   71
CONECT   35   36   37
CONECT   36   72   73   74
CONECT   37   75   76
CONECT   38   39   40   77
CONECT   39   78   79   80
CONECT   40   81   82   83
CONECT   41   42   42   43
END

HMDB0015331
     RDKit          3D
Bromocriptine
 83 89  0  0  0  0  0  0  0  0999 V2000
   -4.1963    3.5565    1.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    3.2632    0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    4.4832   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.0334    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185    0.7854    0.3988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2567    0.4861   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2114    1.2973   -0.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943   -0.6772   -1.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906   -0.9804   -2.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029   -2.4659   -3.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213   -2.5986   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -1.7821   -0.9874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0782   -1.2418   -0.3427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3602   -0.5941   -1.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -2.2417    0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.8516    1.4575 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4327   -1.2518    1.4150 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.7232    2.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192   -0.7885    3.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -0.1034    2.6435 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6128    1.0621    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    0.9006    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    2.0761   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513    3.2357   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    4.2485   -1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    4.1143   -2.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631    2.9252   -2.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    2.4518   -2.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8944    1.1653   -2.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2022    0.0368   -3.3946 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    0.8493   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.9561   -1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -0.3745   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -0.3985   -0.0298 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3572   -1.4409    0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -2.6815    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516   -1.1080    2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089   -3.0618    2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135   -4.1428    1.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -3.6498    2.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -0.8185    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075   -0.4071    3.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -0.3427    0.7063 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    2.7514    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8381    4.4312    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    3.8617    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    3.2698   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    5.3950    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814    4.3399    0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    4.7061   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    2.1815    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285    1.9098   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    0.9728    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6676   -0.7710   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -0.4364   -3.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1233   -3.0243   -2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1633   -2.7052   -4.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -2.0849   -2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -3.6413   -1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706   -2.3357   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.1812   -1.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066   -1.2238    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    0.3007    3.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    2.0727    2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    3.3698    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670    5.2151   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    4.9091   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918    2.9591   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600   -1.2329   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7496   -0.5082    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937   -0.5861   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447   -2.5136    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394   -3.1170   -0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -3.4182    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629   -0.7477    2.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1876   -2.0438    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.8446    3.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -4.5745    2.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114   -3.6694    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794   -4.9666    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520   -3.0072    3.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -4.7101    2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8686   -3.5028    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 16 38  1  0
 38 39  1  0
 38 40  1  0
 16 41  1  0
 41 42  2  0
 41 43  1  0
 43  5  1  0
 12  8  1  0
 43 13  1  0
 37 20  1  0
 34 22  1  0
 32 23  1  0
 32 27  2  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  1
  9 54  1  0
  9 55  1  0
 10 56  1  0
 10 57  1  0
 11 58  1  0
 11 59  1  0
 12 60  1  1
 14 61  1  0
 17 62  1  0
 20 63  1  1
 21 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 28 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  6
 36 72  1  0
 36 73  1  0
 36 74  1  0
 37 75  1  0
 37 76  1  0
 38 77  1  0
 39 78  1  0
 39 79  1  0
 39 80  1  0
 40 81  1  0
 40 82  1  0
 40 83  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5'alpha)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman	ChEBI
(5'alpha)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione	ChEBI
(5'alpha)-2-Bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman	ChEBI
2-Bromo-alpha-ergocryptine	ChEBI
2-Bromo-alpha-ergokryptin	ChEBI
2-Bromo-alpha-ergokryptine	ChEBI
Bromocriptinum	ChEBI
Bromocryptine	ChEBI
Bromoergocriptine	ChEBI
(5'a)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman	Generator
(5'Α)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman	Generator
(5'a)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione	Generator
(5'Α)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione	Generator
(5'a)-2-Bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman	Generator
(5'Α)-2-bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman	Generator
2-Bromo-a-ergocryptine	Generator
2-Bromo-α-ergocryptine	Generator
2-Bromo-a-ergokryptin	Generator
2-Bromo-α-ergokryptin	Generator
2-Bromo-a-ergokryptine	Generator
2-Bromo-α-ergokryptine	Generator
Bromergocryptine	HMDB
Bromocriptin	HMDB
Bromocriptine methanesulfonate	HMDB
Bromoergocryptine	HMDB
2 Bromo alpha ergocryptine	HMDB
2 Bromoergocryptine mesylate	HMDB
2 Bromoergokryptine	HMDB
2-Bromoergocryptine mesylate	HMDB
Mesylate, bromocriptine	HMDB
Methanesulfonate, 2-bromoergocryptine	HMDB
Parlodel	HMDB
2 Bromoergocryptine	HMDB
2 Bromoergocryptine methanesulfonate	HMDB
2-Bromoergocryptine	HMDB
2-Bromoergocryptine methanesulfonate	HMDB
2-Bromoergokryptine	HMDB
Mesylate, 2-bromoergocryptine	HMDB
2 Bromo alpha ergokryptine	HMDB
Bromocriptine mesylate	HMDB
Bromocryptin	HMDB

Chemical Formula

C₃₂H₄₀BrN₅O₅

Average Molecular Weight

654.595

Monoisotopic Molecular Weight

653.221282062

IUPAC Name

(4R,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

bromocriptine

CAS Registry Number

25614-03-3

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C

InChI Identifier

InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1

InChI Key

OZVBMTJYIDMWIL-AYFBDAFISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergamides

Alternative Parents

Substituents

Lysergic acid amide
Indoloquinoline
Benzoquinoline
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Alpha-amino acid or derivatives
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
N-alkylpiperazine
Aryl bromide
Aryl halide
1,4-diazinane
Oxazolidinone
Piperazine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Oxazolidine
Carboxamide group
Lactam
Tertiary amine
Tertiary aliphatic amine
Orthocarboxylic acid derivative
Amino acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Alkanolamine
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:3181 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015331)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

antiparkinson drug (HMDB: HMDB0015331)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

dopamine agonist (HMDB: HMDB0015331)
antidyskinesia agent (HMDB: HMDB0015331)
hormone antagonist (HMDB: HMDB0015331)

Biological role

dopamine agonist (HMDB: HMDB0015331)
hormone antagonist (HMDB: HMDB0015331)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.086 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	244.447	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001359

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.89	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	6.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	165.51 m³·mol⁻¹	ChemAxon
Polarizability	66.44 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	271.224	30932474
DeepCCS	[M+Na]+	244.998	30932474
AllCCS	[M+H]+	238.6	32859911
AllCCS	[M+H-H2O]+	237.9	32859911
AllCCS	[M+NH4]+	239.1	32859911
AllCCS	[M+Na]+	239.3	32859911
AllCCS	[M-H]-	227.3	32859911
AllCCS	[M+Na-2H]-	230.0	32859911
AllCCS	[M+HCOO]-	233.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bromocriptine	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C	5898.6	Standard polar	33892256
Bromocriptine	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C	4251.5	Standard non polar	33892256
Bromocriptine	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C	5139.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bromocriptine,1TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4653.5	Semi standard non polar	33892256
Bromocriptine,1TMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4505.9	Semi standard non polar	33892256
Bromocriptine,1TMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4659.1	Semi standard non polar	33892256
Bromocriptine,2TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4511.3	Semi standard non polar	33892256
Bromocriptine,2TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4733.3	Standard non polar	33892256
Bromocriptine,2TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	6106.8	Standard polar	33892256
Bromocriptine,2TMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4610.7	Semi standard non polar	33892256
Bromocriptine,2TMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4699.1	Standard non polar	33892256
Bromocriptine,2TMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	6116.4	Standard polar	33892256
Bromocriptine,2TMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4536.0	Semi standard non polar	33892256
Bromocriptine,2TMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4747.1	Standard non polar	33892256
Bromocriptine,2TMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	6059.1	Standard polar	33892256
Bromocriptine,3TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4543.0	Semi standard non polar	33892256
Bromocriptine,3TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	4756.7	Standard non polar	33892256
Bromocriptine,3TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N12	5770.4	Standard polar	33892256
Bromocriptine,1TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4845.6	Semi standard non polar	33892256
Bromocriptine,1TBDMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	4721.5	Semi standard non polar	33892256
Bromocriptine,1TBDMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4814.6	Semi standard non polar	33892256
Bromocriptine,2TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	4896.0	Semi standard non polar	33892256
Bromocriptine,2TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	5168.4	Standard non polar	33892256
Bromocriptine,2TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	6104.9	Standard polar	33892256
Bromocriptine,2TBDMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	4966.5	Semi standard non polar	33892256
Bromocriptine,2TBDMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	5142.2	Standard non polar	33892256
Bromocriptine,2TBDMS,isomer #2	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N12	6115.0	Standard polar	33892256
Bromocriptine,2TBDMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	4890.8	Semi standard non polar	33892256
Bromocriptine,2TBDMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	5183.5	Standard non polar	33892256
Bromocriptine,2TBDMS,isomer #3	CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N12	6059.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-9321002000-4a6a862f3d310c4b1ddc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromocriptine GC-MS ("Bromocriptine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 10V, Positive-QTOF	splash10-0udi-0002009000-d51e2392ddc2f88f3e4e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 20V, Positive-QTOF	splash10-0fi0-1019002000-5ec9b007ab29026f0c68	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 40V, Positive-QTOF	splash10-0udi-6029000000-f3b760903bf99f727a1f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 10V, Negative-QTOF	splash10-0udl-0003907000-9135b64a6bbc11172f2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 20V, Negative-QTOF	splash10-0ika-8139817000-f971791e9c2caf9b0175	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 40V, Negative-QTOF	splash10-01ba-9301000000-344064b476a208775714	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 10V, Positive-QTOF	splash10-0udi-0000009000-a432702c23226daf972f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 20V, Positive-QTOF	splash10-0udi-0045019000-a5eeda23fd43d5879469	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 40V, Positive-QTOF	splash10-0udi-2049004000-149f9f3768b43e24b56f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 10V, Negative-QTOF	splash10-0udi-0000009000-e2c1692967aaeab3212f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 20V, Negative-QTOF	splash10-0udi-1031319000-12704c05dc3bfba9eb19	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromocriptine 40V, Negative-QTOF	splash10-00vi-9143001000-068ff47eb0d7789a1ad2	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01200	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01200	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01200

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28858

KEGG Compound ID

C06856

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bromocriptine

METLIN ID

Not Available

PubChem Compound

31101

PDB ID

Not Available

ChEBI ID

3181

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
Malgaroli A, Vallar L, Elahi FR, Pozzan T, Spada A, Meldolesi J: Dopamine inhibits cytosolic Ca2+ increases in rat lactotroph cells. Evidence of a dual mechanism of action. J Biol Chem. 1987 Oct 15;262(29):13920-7. [PubMed:2443499 ]
Vallar L, Meldolesi J: Mechanisms of signal transduction at the dopamine D2 receptor. Trends Pharmacol Sci. 1989 Feb;10(2):74-7. [PubMed:2655242 ]
Vallar L, Vicentini LM, Meldolesi J: Inhibition of inositol phosphate production is a late, Ca2+-dependent effect of D2 dopaminergic receptor activation in rat lactotroph cells. J Biol Chem. 1988 Jul 25;263(21):10127-34. [PubMed:2839476 ]
Banihashemi B, Albert PR: Dopamine-D2S receptor inhibition of calcium influx, adenylyl cyclase, and mitogen-activated protein kinase in pituitary cells: distinct Galpha and Gbetagamma requirements. Mol Endocrinol. 2002 Oct;16(10):2393-404. [PubMed:12351703 ]
Nishina Y, Takano K, Yasufuku-Takano J, Teramoto A, Fujita T: Mechanism of D(2) agonist-induced inhibition of GH secretion from human GH-secreting adenoma cells. Endocr J. 2005 Dec;52(6):775-9. [PubMed:16410672 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Fernando H, Halpert JR, Davydov DR: Resolution of multiple substrate binding sites in cytochrome P450 3A4: the stoichiometry of the enzyme-substrate complexes probed by FRET and Job's titration. Biochemistry. 2006 Apr 4;45(13):4199-209. [PubMed:16566594 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Nath A, Grinkova YV, Sligar SG, Atkins WM: Ligand binding to cytochrome P450 3A4 in phospholipid bilayer nanodiscs: the effect of model membranes. J Biol Chem. 2007 Sep 28;282(39):28309-20. Epub 2007 Jun 15. [PubMed:17573349 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

de Leeuw van Weenen JE, Parlevliet ET, Maechler P, Havekes LM, Romijn JA, Ouwens DM, Pijl H, Guigas B: The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells. Biochem Pharmacol. 2010 Jun 15;79(12):1827-36. doi: 10.1016/j.bcp.2010.01.029. Epub 2010 Feb 4. [PubMed:20138024 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Enzyme Details

4. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

de Leeuw van Weenen JE, Parlevliet ET, Maechler P, Havekes LM, Romijn JA, Ouwens DM, Pijl H, Guigas B: The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells. Biochem Pharmacol. 2010 Jun 15;79(12):1827-36. doi: 10.1016/j.bcp.2010.01.029. Epub 2010 Feb 4. [PubMed:20138024 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Enzyme Details

5. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Cavallotti C, Nuti F, Bruzzone P, Mancone M: Age-related changes in dopamine D2 receptors in rat heart and coronary vessels. Clin Exp Pharmacol Physiol. 2002 May-Jun;29(5-6):412-8. [PubMed:12010185 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
Lahlou S: Cardiovascular responses to intrathecal dopamine receptor agonists in conscious DOCA-salt hypertensive rats. Fundam Clin Pharmacol. 1999;13(6):624-34. [PubMed:10626749 ]
Lahlou S, Araujo Lima PF, Interaminense LF, Duarte GP: Blunted central bromocriptine-induced tachycardia in conscious, malnourished rats. Pharmacol Toxicol. 2003 Apr;92(4):189-94. [PubMed:12753422 ]
Lahlou S, Lima GC, Leao-Filho CS, Duarte GP: Effects of long-term pretreatment with isoproterenol on bromocriptine-induced tachycardia in conscious rats. Can J Physiol Pharmacol. 2000 Mar;78(3):260-5. [PubMed:10721819 ]
Stefaneanu L, Kovacs K, Horvath E, Buchfelder M, Fahlbusch R, Lancranjan L: Dopamine D2 receptor gene expression in human adenohypophysial adenomas. Endocrine. 2001 Apr;14(3):329-36. [PubMed:11444429 ]

Enzyme Details

6. 5-hydroxytryptamine receptor 7

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:: HTR7
Uniprot ID:: P34969
Molecular weight:: 53554.4

References

Knight JA, Smith C, Toohey N, Klein MT, Teitler M: Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists. Mol Pharmacol. 2009 Feb;75(2):374-80. doi: 10.1124/mol.108.052084. Epub 2008 Nov 7. [PubMed:18996971 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 2B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2B
Uniprot ID:: P41595
Molecular weight:: 54297.4

References

Cussac D, Boutet-Robinet E, Ailhaud MC, Newman-Tancredi A, Martel JC, Danty N, Rauly-Lestienne I: Agonist-directed trafficking of signalling at serotonin 5-HT2A, 5-HT2B and 5-HT2C-VSV receptors mediated Gq/11 activation and calcium mobilisation in CHO cells. Eur J Pharmacol. 2008 Oct 10;594(1-3):32-8. doi: 10.1016/j.ejphar.2008.07.040. Epub 2008 Jul 30. [PubMed:18703043 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Enzyme Details

9. D(4) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]
Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
Renaud JP, Davydov DR, Heirwegh KP, Mansuy D, Hui Bon Hoa GH: Thermodynamic studies of substrate binding and spin transitions in human cytochrome P-450 3A4 expressed in yeast microsomes. Biochem J. 1996 Nov 1;319 ( Pt 3):675-81. [PubMed:8920966 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for Bromocriptine (HMDB0015331)

MOL for HMDB0015331 (Bromocriptine)

3D MOL for HMDB0015331 (Bromocriptine)

3D SDF for HMDB0015331 (Bromocriptine)

3D-SDF for HMDB0015331 (Bromocriptine)

PDB for HMDB0015331 (Bromocriptine)

3D PDB for HMDB0015331 (Bromocriptine)

SMILES for HMDB0015331 (Bromocriptine)

INCHI for HMDB0015331 (Bromocriptine)

Structure for HMDB0015331 (Bromocriptine)

3D Structure for HMDB0015331 (Bromocriptine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References

Transporters

References