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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015383

Secondary Accession Numbers

HMDB15383

Metabolite Identification

Common Name

Ergonovine

Description

Ergonovine is only found in individuals that have used or taken this drug. It is an ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem]Ergonovine directly stimulates the uterine muscle to increase force and frequency of contractions. With usual doses, these contractions precede periods of relaxation; with larger doses, basal uterine tone is elevated and these relaxation periods will be decreased. Contraction of the uterine wall around bleeding vessels at the placental site produces hemostasis. Ergonovine also induces cervical contractions. The sensitivity of the uterus to the oxytocic effect is much greater toward the end of pregnancy. The oxytocic actions of ergonovine are greater than its vascular effects. Ergonovine, like other ergot alkaloids, produces arterial vasoconstriction by stimulation of alpha-adrenergic and serotonin receptors and inhibition of endothelial-derived relaxation factor release. It is a less potent vasoconstrictor than ergotamine. As a diagnostic aid (coronary vasospasm), ergonovine causes vasoconstriction of coronary arteries.

Structure

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

1253
  Mrv0541 02231215212D          

 25 28  0  0  1  0            999 V2000
    2.3776    0.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    3.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2666   -3.1748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872    1.4617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5639   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065    0.2270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5507    0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -2.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -3.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0108    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6009   -2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905    0.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -3.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -3.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712    1.8715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3680    2.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    1.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -0.3124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  2  0  0  0  0
  2 23  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 18  1  0  0  0  0
 22  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 25  1  1  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 18  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END

HMDB0015383
     RDKit          3D
Ergonovine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.3657    0.3058    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    0.9789   -0.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4552    0.9342   -1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.3888   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3660    0.2408   -0.5685 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0994    0.8185   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    2.0048   -0.0043 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.0047   -0.5594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2919    0.8110   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.2333    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    1.0300    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4534    2.3911    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    3.0412    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    2.3645    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.0011    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8940    0.0291    0.7776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2827   -1.1640    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093   -0.9598    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684    0.3897    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403   -1.8216    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680   -1.2108    0.5625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3041   -1.9804    0.2708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -2.8145   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -1.3081    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362   -0.7994    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    0.6604    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100    0.5388    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3451    2.0075   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732    1.3476   -2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657    1.5349   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5772   -0.6496   -1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736   -0.7729   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657   -0.2382   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.8862   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176    2.8815    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    4.1073    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7860    2.9124    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9037    0.2127    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8222   -2.0827    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.0792   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -2.7720    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -1.2524    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -3.5639   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -3.4179   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -2.2547   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -1.1468    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -1.9902   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24  8  1  0
 21 10  1  0
 19 11  1  0
 19 15  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  1
 23 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
M  END

1253
  Mrv0541 02231215212D          

 25 28  0  0  1  0            999 V2000
    2.3776    0.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    3.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    0.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2666   -3.1748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872    1.4617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5639   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065    0.2270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5507    0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -2.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -3.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0108    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6009   -2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905    0.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -3.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -3.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712    1.8715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3680    2.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    1.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -0.3124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  2  0  0  0  0
  2 23  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 18  1  0  0  0  0
 22  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 25  1  1  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 18  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015383

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1

> <INCHI_KEY>
WVVSZNPYNCNODU-XTQGRXLLSA-N

> <FORMULA>
C19H23N3O2

> <MOLECULAR_WEIGHT>
325.4048

> <EXACT_MASS>
325.179026995

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.53515172912834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,7R)-N-[(2S)-1-hydroxypropan-2-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>
1.53

> <JCHEM_LOGP>
1.0706959856666662

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.936197047508507

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.998553275855407

> <JCHEM_PKA_STRONGEST_BASIC>
7.9273088332375305

> <JCHEM_POLAR_SURFACE_AREA>
68.36

> <JCHEM_REFRACTIVITY>
95.05190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ergonovine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015383
     RDKit          3D
Ergonovine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.3657    0.3058    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    0.9789   -0.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4552    0.9342   -1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.3888   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3660    0.2408   -0.5685 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0994    0.8185   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    2.0048   -0.0043 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.0047   -0.5594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2919    0.8110   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.2333    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    1.0300    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4534    2.3911    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    3.0412    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    2.3645    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.0011    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8940    0.0291    0.7776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2827   -1.1640    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093   -0.9598    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684    0.3897    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403   -1.8216    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680   -1.2108    0.5625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3041   -1.9804    0.2708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -2.8145   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -1.3081    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362   -0.7994    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    0.6604    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100    0.5388    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3451    2.0075   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732    1.3476   -2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657    1.5349   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5772   -0.6496   -1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736   -0.7729   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657   -0.2382   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.8862   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176    2.8815    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    4.1073    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7860    2.9124    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9037    0.2127    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8222   -2.0827    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.0792   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -2.7720    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -1.2524    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -3.5639   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -3.4179   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -2.2547   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -1.1468    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -1.9902   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24  8  1  0
 21 10  1  0
 19 11  1  0
 19 15  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  1
 23 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1253                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.438   0.413   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.084   5.798   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.878   0.413   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.698  -5.926   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.763   2.729   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.853  -1.191   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.519  -1.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.187  -1.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.105   0.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.495   1.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.187  -3.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.519  -3.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.853  -4.271   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.118  -1.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.878  -5.875   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.220   1.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.322  -4.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.769   1.189   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.118  -4.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.495  -6.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.105  -5.885   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.426   3.493   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.420   5.033   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.095   2.718   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      10.925  -0.583   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   23                                                            
CONECT    3    6   10   16                                                  
CONECT    4   15   17                                                       
CONECT    5   18   22                                                       
CONECT    6    3    7    8   25                                             
CONECT    7    6   12   14                                                  
CONECT    8    6   11                                                       
CONECT    9   10   14   18                                                  
CONECT   10    3    9                                                       
CONECT   11    8   13   17                                                  
CONECT   12    7   13   19                                                  
CONECT   13   11   12   15                                                  
CONECT   14    7    9                                                       
CONECT   15    4   13   20                                                  
CONECT   16    3                                                            
CONECT   17    4   11                                                       
CONECT   18    1    5    9                                                  
CONECT   19   12   21                                                       
CONECT   20   15   21                                                       
CONECT   21   19   20                                                       
CONECT   22    5   23   24                                                  
CONECT   23    2   22                                                       
CONECT   24   22                                                            
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0015383
HETATM    1  C1  UNL     1       5.366   0.306   0.735  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.580   0.979  -0.389  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.455   0.934  -1.623  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.787  -0.389  -1.909  1.00  0.00           O  
HETATM    5  N1  UNL     1       3.366   0.241  -0.569  1.00  0.00           N  
HETATM    6  C4  UNL     1       2.099   0.818  -0.357  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.013   2.005  -0.004  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.894   0.005  -0.559  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.292   0.811  -0.283  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.362   0.233   0.232  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.556   1.030   0.513  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.453   2.391   0.727  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.675   3.041   0.994  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.885   2.365   1.037  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.969   1.001   0.821  1.00  0.00           C  
HETATM   16  N2  UNL     1      -5.894   0.029   0.778  1.00  0.00           N  
HETATM   17  C13 UNL     1      -5.283  -1.164   0.498  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.909  -0.960   0.355  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.768   0.390   0.563  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.740  -1.822   0.050  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.468  -1.211   0.563  1.00  0.00           C  
HETATM   22  N3  UNL     1      -0.304  -1.980   0.271  1.00  0.00           N  
HETATM   23  C18 UNL     1      -0.529  -2.814  -0.893  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.922  -1.308   0.153  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.336  -0.799   0.644  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.410   0.660   0.753  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.910   0.539   1.731  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.345   2.008  -0.078  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.973   1.348  -2.516  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.366   1.535  -1.408  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.577  -0.650  -1.373  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.474  -0.773  -0.872  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.866  -0.238  -1.664  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.272   1.886  -0.511  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.518   2.882   0.690  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.613   4.107   1.163  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.786   2.912   1.245  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.904   0.213   0.939  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.822  -2.083   0.414  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.689  -2.079  -1.028  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.897  -2.772   0.633  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.570  -1.252   1.693  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.334  -3.564  -0.691  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.416  -3.418  -1.019  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.668  -2.255  -1.820  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.362  -1.147   1.160  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.645  -1.990  -0.381  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    5   28
CONECT    3    4   29   30
CONECT    4   31
CONECT    5    6   32
CONECT    6    7    7    8
CONECT    8    9   24   33
CONECT    9   10   10   34
CONECT   10   11   21
CONECT   11   12   12   19
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   19   19
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   20   21   40   41
CONECT   21   22   42
CONECT   22   23   24
CONECT   23   43   44   45
CONECT   24   46   47
END

HMDB0015383
     RDKit          3D
Ergonovine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.3657    0.3058    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    0.9789   -0.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4552    0.9342   -1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.3888   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3660    0.2408   -0.5685 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0994    0.8185   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    2.0048   -0.0043 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.0047   -0.5594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2919    0.8110   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.2333    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    1.0300    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4534    2.3911    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    3.0412    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    2.3645    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.0011    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8940    0.0291    0.7776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2827   -1.1640    0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093   -0.9598    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684    0.3897    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403   -1.8216    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680   -1.2108    0.5625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3041   -1.9804    0.2708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295   -2.8145   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -1.3081    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362   -0.7994    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    0.6604    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100    0.5388    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3451    2.0075   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732    1.3476   -2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657    1.5349   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5772   -0.6496   -1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736   -0.7729   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657   -0.2382   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.8862   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176    2.8815    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    4.1073    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7860    2.9124    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9037    0.2127    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8222   -2.0827    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.0792   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -2.7720    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -1.2524    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -3.5639   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -3.4179   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -2.2547   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -1.1468    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -1.9902   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24  8  1  0
 21 10  1  0
 19 11  1  0
 19 15  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  6
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  1
 23 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide	ChEBI
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamide	ChEBI
9,10-Didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide	ChEBI
[8beta(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide	ChEBI
D-Lysergic acid 1-hydroxymethylethylamide	ChEBI
D-Lysergic acid-L-propanolamide	ChEBI
Ergobasine	ChEBI
Ergometrina	ChEBI
Ergometrinum	ChEBI
Ergotocine	ChEBI
Margonovine	ChEBI
N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamide	ChEBI
N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamide	ChEBI
Ergometrine	Kegg
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylate ((S)-2-hydroxy-1-methyl-ethyl)-amide	Generator
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8b(S)-carboxamide	Generator
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8β(S)-carboxamide	Generator
9,10-Didehydro-N-(a-(hydroxymethyl)ethyl)-6-methylergoline-8-b-carboxamide	Generator
9,10-Didehydro-N-(α-(hydroxymethyl)ethyl)-6-methylergoline-8-β-carboxamide	Generator
[8b(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide	Generator
[8Β(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide	Generator
D-Lysergate 1-hydroxymethylethylamide	Generator
D-Lysergate-L-propanolamide	Generator
N-(a-(Hydroxymethyl)ethyl)-D-lysergamide	Generator
N-(Α-(hydroxymethyl)ethyl)-D-lysergamide	Generator
Ergotrate maleate	HMDB
Bedford brand OF ergonovine maleate	HMDB
Ergobasin	HMDB
Ergometrin	HMDB
Ergotrate	HMDB
Ergometrine maleate	HMDB
Ergonovine maleate	HMDB
Ergonovine	ChEBI

Chemical Formula

C₁₉H₂₃N₃O₂

Average Molecular Weight

325.4048

Monoisotopic Molecular Weight

325.179026995

IUPAC Name

(4R,7R)-N-[(2S)-1-hydroxypropan-2-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

ergonovine

CAS Registry Number

60-79-7

SMILES

[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO

InChI Identifier

InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1

InChI Key

WVVSZNPYNCNODU-XTQGRXLLSA-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
Pyrroloquinoline
Quinoline-3-carboxamide
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Primary alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4822 )
organic heterotetracyclic compound (CHEBI:4822 )
monocarboxylic acid amide (CHEBI:4822 )
secondary amino compound (CHEBI:4822 )
ergot alkaloid (CHEBI:4822 )
primary alcohol (CHEBI:4822 )
Indole alkaloids (C07543 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015383)

Process

Not Available

Role

Industrial application

Diagnostic agent (HMDB: HMDB0015383)
Oxytocic (HMDB: HMDB0015383)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.32 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	178.952	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001366

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.07	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.05 m³·mol⁻¹	ChemAxon
Polarizability	36.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	177.105	31661259
DarkChem	[M-H]-	172.483	31661259
DeepCCS	[M-2H]-	214.975	30932474
DeepCCS	[M+Na]+	190.042	30932474
AllCCS	[M+H]+	179.6	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	182.4	32859911
AllCCS	[M+Na]+	183.2	32859911
AllCCS	[M-H]-	182.9	32859911
AllCCS	[M+Na-2H]-	182.8	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.54 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2211 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	125.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1116.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	272.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	303.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	506.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	734.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	300.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1013.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	372.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	69.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO	4629.0	Standard polar	33892256
Ergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO	3357.0	Standard non polar	33892256
Ergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO	3439.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ergonovine,1TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1	3011.6	Semi standard non polar	33892256
Ergonovine,1TMS,isomer #2	C[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3013.9	Semi standard non polar	33892256
Ergonovine,1TMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	2968.7	Semi standard non polar	33892256
Ergonovine,2TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3007.1	Semi standard non polar	33892256
Ergonovine,2TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3200.3	Standard non polar	33892256
Ergonovine,2TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3898.8	Standard polar	33892256
Ergonovine,2TMS,isomer #2	C[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	2958.4	Semi standard non polar	33892256
Ergonovine,2TMS,isomer #2	C[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3144.1	Standard non polar	33892256
Ergonovine,2TMS,isomer #2	C[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3865.3	Standard polar	33892256
Ergonovine,2TMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	2940.7	Semi standard non polar	33892256
Ergonovine,2TMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3153.4	Standard non polar	33892256
Ergonovine,2TMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3914.7	Standard polar	33892256
Ergonovine,3TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3005.5	Semi standard non polar	33892256
Ergonovine,3TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3203.5	Standard non polar	33892256
Ergonovine,3TMS,isomer #1	C[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3659.7	Standard polar	33892256
Ergonovine,1TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1	3254.9	Semi standard non polar	33892256
Ergonovine,1TBDMS,isomer #2	C[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3228.2	Semi standard non polar	33892256
Ergonovine,1TBDMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3176.4	Semi standard non polar	33892256
Ergonovine,2TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3409.2	Semi standard non polar	33892256
Ergonovine,2TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3676.6	Standard non polar	33892256
Ergonovine,2TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3997.7	Standard polar	33892256
Ergonovine,2TBDMS,isomer #2	C[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3386.3	Semi standard non polar	33892256
Ergonovine,2TBDMS,isomer #2	C[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3574.8	Standard non polar	33892256
Ergonovine,2TBDMS,isomer #2	C[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3976.9	Standard polar	33892256
Ergonovine,2TBDMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3339.4	Semi standard non polar	33892256
Ergonovine,2TBDMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3614.6	Standard non polar	33892256
Ergonovine,2TBDMS,isomer #3	C[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	4001.6	Standard polar	33892256
Ergonovine,3TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3563.1	Semi standard non polar	33892256
Ergonovine,3TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3856.0	Standard non polar	33892256
Ergonovine,3TBDMS,isomer #1	C[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3823.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ergonovine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3931000000-4bdb2fafa3f7edc31959	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergonovine GC-MS (1 TMS) - 70eV, Positive	splash10-006t-3941000000-efd4dcb7883cfc33a6d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergonovine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergonovine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Ergonovine 10V, Positive-QTOF	splash10-056r-1029000000-c07ebacb47f673bb1d1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 20V, Positive-QTOF	splash10-0kmi-2093000000-ac375307cfa93e46e2b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 40V, Positive-QTOF	splash10-00dl-3930000000-6800151137f550b0b24f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 10V, Negative-QTOF	splash10-00di-0029000000-87d6fc7041cc0a8ae488	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 20V, Negative-QTOF	splash10-05fr-4189000000-1718640f639f14c8ffbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 40V, Negative-QTOF	splash10-05fu-9270000000-c5c258e619a7caf0d202	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 10V, Positive-QTOF	splash10-0fb9-0049000000-d4507ba5008088f43bb2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 20V, Positive-QTOF	splash10-004i-1096000000-f48fc1c59c03b2f4eeed	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 40V, Positive-QTOF	splash10-00di-1390000000-583fd193eccec822fff6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 10V, Negative-QTOF	splash10-00di-0019000000-282ccc4ee74de31656ff	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 20V, Negative-QTOF	splash10-05fu-4049000000-f096fd02d1574a188595	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergonovine 40V, Negative-QTOF	splash10-06dl-5390000000-4b659d3b0f488353d51d	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 DB01253	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01253	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

DB01253

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ergometrine

METLIN ID

Not Available

PubChem Compound

443884

PDB ID

Not Available

ChEBI ID

4822

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

Not Available

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

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 ]
Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [PubMed:12583687 ]

Enzyme Details

2. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Gibson A, Carvajal A: Agonist profile of ergometrine (ergonovine) on a population of postsynaptic alpha-adrenoceptors. J Pharm Pharmacol. 1988 Feb;40(2):137-9. [PubMed:2897449 ]
Zhu F, Han B, Kumar P, Liu X, Ma X, Wei X, Huang L, Guo Y, Han L, Zheng C, Chen Y: Update of TTD: Therapeutic Target Database. Nucleic Acids Res. 2010 Jan;38(Database issue):D787-91. doi: 10.1093/nar/gkp1014. Epub 2009 Nov 20. [PubMed:19933260 ]

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 ]

Showing metabocard for Ergonovine (HMDB0015383)

MOL for HMDB0015383 (Ergonovine)

3D MOL for HMDB0015383 (Ergonovine)

3D SDF for HMDB0015383 (Ergonovine)

3D-SDF for HMDB0015383 (Ergonovine)

PDB for HMDB0015383 (Ergonovine)

3D PDB for HMDB0015383 (Ergonovine)

SMILES for HMDB0015383 (Ergonovine)

INCHI for HMDB0015383 (Ergonovine)

Structure for HMDB0015383 (Ergonovine)

3D Structure for HMDB0015383 (Ergonovine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References