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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:59:04 UTC

Update Date

2021-09-14 15:45:38 UTC

HMDB ID

HMDB0060782

Secondary Accession Numbers

HMDB60782

Metabolite Identification

Common Name

6-allyl-8b-Carboxy-ergoline

Description

6-allyl-8b-Carboxy-ergoline is a metabolite of cabergoline. Cabergoline (brand names Dostinex and Cabaser), an ergot derivative, is a potent dopamine receptor agonist on D2 receptors. In vitro, rat studies show cabergoline has a direct inhibitory effect on pituitary lactotroph cells. It is frequently used as a first-line agent in the management of prolactinomas due to higher affinity for D2 receptor sites, less severe side effects, and more convenient dosing schedule than the older bromocriptine. (Wikipedia)

Structure

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

HMDB0060782
     RDKit          3D
6-allyl-8b-Carboxy-ergoline
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0514   -3.5857    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1532   -2.8073    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772   -1.4707   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.4250    0.2018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2985    0.9011   -0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    1.8984    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    3.2405    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    3.3821   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    4.3680    1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577    1.5544    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890    0.8550    0.4603 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6215    0.6523    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963    1.3377    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.0487    1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    0.0979    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685   -0.5860   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.5478   -1.0628 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -1.8254   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -1.0371   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -0.2842   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -0.8300   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134   -0.5172    0.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0803   -3.2993    0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7425   -4.5618    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398   -3.1843   -0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -1.3293   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247   -1.3809   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075    0.8664   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    1.1631   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6529    1.8997    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    4.3037    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616    2.4912    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6700    0.9607    2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.4462   -0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    2.0612    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348    1.6043    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944   -0.1173    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -1.9657   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -2.5433   -2.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.6806   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.0769   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.2305    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  4  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  6
 13 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  1
M  END


  Mrv0541 07041311592D          

 22 25  0  0  0  0            999 V2000
   -3.7004   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -1.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -2.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -2.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.9795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.3911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5605   -3.8661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -3.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  6  0  0  0
 15  5  2  0  0  0  0
 16  8  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 20  6  1  0  0  0  0
 20 10  1  0  0  0  0
 16 20  1  1  0  0  0
 21 18  2  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060782

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2O2/c1-2-6-20-10-12(18(21)22)7-14-13-4-3-5-15-17(13)11(9-19-15)8-16(14)20/h2-5,9,12,14,16,19H,1,6-8,10H2,(H,21,22)/t12?,14-,16-/m0/s1

> <INCHI_KEY>
YAICYXFUKKMAKO-DBQWNMKUSA-N

> <FORMULA>
C18H20N2O2

> <MOLECULAR_WEIGHT>
296.3636

> <EXACT_MASS>
296.152477894

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.20186623445876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
0.13126856425200908

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.05889364622908

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.816031591017574

> <JCHEM_PKA_STRONGEST_BASIC>
8.537177584550946

> <JCHEM_POLAR_SURFACE_AREA>
56.33

> <JCHEM_REFRACTIVITY>
86.0116

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060782
     RDKit          3D
6-allyl-8b-Carboxy-ergoline
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0514   -3.5857    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1532   -2.8073    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772   -1.4707   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.4250    0.2018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2985    0.9011   -0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    1.8984    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    3.2405    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    3.3821   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    4.3680    1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577    1.5544    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890    0.8550    0.4603 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6215    0.6523    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963    1.3377    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.0487    1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    0.0979    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685   -0.5860   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.5478   -1.0628 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -1.8254   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -1.0371   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -0.2842   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -0.8300   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134   -0.5172    0.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0803   -3.2993    0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7425   -4.5618    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398   -3.1843   -0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -1.3293   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247   -1.3809   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075    0.8664   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    1.1631   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6529    1.8997    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    4.3037    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616    2.4912    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6700    0.9607    2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.4462   -0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    2.0612    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348    1.6043    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944   -0.1173    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -1.9657   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -2.5433   -2.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.6806   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.0769   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.2305    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  4  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  6
 13 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  1
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -6.907  -1.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.575  -2.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.240  -1.825   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.242  -4.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.909  -4.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.576  -4.908   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.573  -1.828   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.578  -6.448   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -2.907  -2.597   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -2.913  -7.217   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.245  -7.220   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3   13                                                       
CONECT    5    3   15                                                       
CONECT    6    2   20                                                       
CONECT    7   12   14                                                       
CONECT    8   11   16                                                       
CONECT    9   11   19                                                       
CONECT   10   12   20                                                       
CONECT   11    8    9   17                                                  
CONECT   12    7   10   18                                                  
CONECT   13    4   14   17                                                  
CONECT   14    7   13   16                                                  
CONECT   15    5   17   19                                                  
CONECT   16    8   14   20                                                  
CONECT   17   11   13   15                                                  
CONECT   18   12   21   22                                                  
CONECT   19    9   15                                                       
CONECT   20    6   10   16                                                  
CONECT   21   18                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060782
HETATM    1  C1  UNL     1      -3.051  -3.586   0.645  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.153  -2.807   0.052  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.577  -1.471  -0.411  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.835  -0.425   0.202  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.298   0.901  -0.159  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.931   1.898   0.920  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.868   3.241   0.301  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.114   3.382  -0.919  1.00  0.00           O  
HETATM    9  O2  UNL     1      -1.538   4.368   1.051  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.558   1.554   1.522  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.189   0.855   0.460  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.622   0.652   0.649  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.396   1.338   1.562  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.744   1.049   1.616  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.341   0.098   0.787  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.569  -0.586  -0.123  1.00  0.00           C  
HETATM   17  N2  UNL     1       3.778  -1.548  -1.063  1.00  0.00           N  
HETATM   18  C14 UNL     1       2.585  -1.825  -1.661  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.603  -1.037  -1.102  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.244  -0.284  -0.157  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.136  -0.830  -1.257  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.413  -0.517   0.122  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.080  -3.299   0.811  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.743  -4.562   0.983  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.140  -3.184  -0.068  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.644  -1.329  -0.154  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.525  -1.381  -1.519  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.408   0.866  -0.206  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.837   1.163  -1.128  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.653   1.900   1.737  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.596   4.304   2.056  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.062   2.491   1.769  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.670   0.961   2.441  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.073   1.446  -0.495  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.899   2.061   2.182  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.335   1.604   2.347  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.394  -0.117   0.841  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.712  -1.966  -1.251  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.413  -2.543  -2.449  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.360  -1.681  -1.708  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.015   0.077  -1.880  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.039  -1.231   0.836  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   22
CONECT    5    6   28   29
CONECT    6    7   10   30
CONECT    7    8    8    9
CONECT    9   31
CONECT   10   11   32   33
CONECT   11   12   22   34
CONECT   12   13   13   20
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   16   37
CONECT   16   17   20   20
CONECT   17   18   38
CONECT   18   19   19   39
CONECT   19   20   21
CONECT   21   22   40   41
CONECT   22   42
END

HMDB0060782
     RDKit          3D
6-allyl-8b-Carboxy-ergoline
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0514   -3.5857    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1532   -2.8073    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772   -1.4707   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.4250    0.2018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2985    0.9011   -0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    1.8984    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    3.2405    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    3.3821   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    4.3680    1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577    1.5544    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890    0.8550    0.4603 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6215    0.6523    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963    1.3377    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.0487    1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    0.0979    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685   -0.5860   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.5478   -1.0628 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -1.8254   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -1.0371   -1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -0.2842   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -0.8300   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134   -0.5172    0.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0803   -3.2993    0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7425   -4.5618    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398   -3.1843   -0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -1.3293   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247   -1.3809   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075    0.8664   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    1.1631   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6529    1.8997    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    4.3037    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616    2.4912    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6700    0.9607    2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.4462   -0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    2.0612    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348    1.6043    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944   -0.1173    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -1.9657   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -2.5433   -2.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.6806   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.0769   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.2305    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  4  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  6
 13 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀N₂O₂

Average Molecular Weight

296.3636

Monoisotopic Molecular Weight

296.152477894

IUPAC Name

(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid

Traditional Name

(2S,7S)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1

InChI Identifier

InChI=1S/C18H20N2O2/c1-2-6-20-10-12(18(21)22)7-14-13-4-3-5-15-17(13)11(9-19-15)8-16(14)20/h2-5,9,12,14,16,19H,1,6-8,10H2,(H,21,22)/t12?,14-,16-/m0/s1

InChI Key

YAICYXFUKKMAKO-DBQWNMKUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lysergic acids. These are derivatives of lysergic acid are amides in which the amidic moiety is formed by a small peptide or an alkylamide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergic acids

Alternative Parents

Substituents

Lysergic acid
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline-3-carboxylic acid
3-alkylindole
Quinoline
Indole
Indole or derivatives
Isoindole or derivatives
Piperidinecarboxylic acid
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060782)
Liver (HMDB: HMDB0060782)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060782)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060782)

Cellular substructure

Cytoplasm (HMDB: HMDB0060782)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.7	ALOGPS
logP	0.13	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	8.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.01 m³·mol⁻¹	ChemAxon
Polarizability	33.2 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]+	170.056	31661259
DarkChem	[M-H]-	170.345	31661259
DeepCCS	[M-2H]-	205.776	30932474
DeepCCS	[M+Na]+	180.913	30932474
AllCCS	[M+H]+	171.0	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	174.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-allyl-8b-Carboxy-ergoline	OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1	4422.6	Standard polar	33892256
6-allyl-8b-Carboxy-ergoline	OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1	2698.6	Standard non polar	33892256
6-allyl-8b-Carboxy-ergoline	OC(=O)C1C[C@@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(CC=C)C1	3018.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-allyl-8b-Carboxy-ergoline,1TMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C)C[C@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@@H]21	2648.8	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,1TMS,isomer #2	C=CCN1CC(C(=O)O)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@@H]21	2713.4	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@@H]21	2659.9	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@@H]21	2776.8	Standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@@H]21	3324.7	Standard polar	33892256
6-allyl-8b-Carboxy-ergoline,1TBDMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@@H]21	2915.7	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,1TBDMS,isomer #2	C=CCN1CC(C(=O)O)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@@H]21	2961.3	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TBDMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@@H]21	3053.5	Semi standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TBDMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@@H]21	3275.5	Standard non polar	33892256
6-allyl-8b-Carboxy-ergoline,2TBDMS,isomer #1	C=CCN1CC(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@@H]21	3468.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-allyl-8b-Carboxy-ergoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4j-2980000000-76cae1d8424dfce15bec	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-allyl-8b-Carboxy-ergoline GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9562000000-65ab2a718e6b497d43a8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-allyl-8b-Carboxy-ergoline 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 - 6-allyl-8b-Carboxy-ergoline 10V, Positive-QTOF	splash10-002b-0090000000-9a9af1b285c8c480ada4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 20V, Positive-QTOF	splash10-002f-3090000000-8ffb90c1d1c03f32eacf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 40V, Positive-QTOF	splash10-0006-9540000000-375d1aa87f5ac4c528bd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 10V, Negative-QTOF	splash10-0002-0090000000-cd483a3ffe2e812ad8a8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 20V, Negative-QTOF	splash10-0udi-0090000000-237c8a3695e0fe5c6d9b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 40V, Negative-QTOF	splash10-0bt9-1290000000-4ba40ff493211410f53c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 10V, Negative-QTOF	splash10-0002-0090000000-15c1a9478cee3b415a5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 20V, Negative-QTOF	splash10-0a4j-0090000000-ed655009859f92144f49	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 40V, Negative-QTOF	splash10-0pvi-0690000000-1c9af694b2ff06794887	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 10V, Positive-QTOF	splash10-0002-0090000000-2a71439addcc9f281845	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 20V, Positive-QTOF	splash10-0005-0390000000-dc97bd818a70a0c424dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-allyl-8b-Carboxy-ergoline 40V, Positive-QTOF	splash10-0gi0-1940000000-ca6220ded6965cd0e482	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769949

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for 6-allyl-8b-Carboxy-ergoline (HMDB0060782)

MOL for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

3D MOL for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

3D SDF for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

3D-SDF for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

PDB for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

3D PDB for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

SMILES for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

INCHI for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

Structure for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

3D Structure for HMDB0060782 (6-allyl-8b-Carboxy-ergoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra