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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19) Show 19 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015317

Secondary Accession Numbers

HMDB15317

Metabolite Identification

Common Name

Pergolide

Description

Pergolide is a long-acting dopamine agonist approved in 1982 for the treatment of Parkinson's Disease. It is an ergot derivative that acts on the dopamine D2 and D3, alpha2- and alpha1-adrenergic, and 5-hydroxytryptamine (5-HT) receptors. It was indicated as adjunct therapy with levodopa/carbidopa in the symptomatic treatment of parkinsonian syndrome. It was later found that pergolide increased the risk of cardiac valvulopathy. The drug was withdrawn from the US market in March 2007 and from the Canadian market in August 2007.

Structure

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

HMDB0015317
     RDKit          3D
Pergolide
 48 51  0  0  0  0  0  0  0  0999 V2000
    3.5570   -2.7511    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -3.2492    0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -2.2874    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.2202    0.1898 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.2558    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963    1.1180   -0.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4434    2.0900    0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753    3.8002    0.2252 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    3.9919   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795    1.5609   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6291    0.4757   -0.6949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0581    0.8384   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250    2.1445   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    2.3310   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071    1.2959   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3318   -0.0005   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -1.2225   -0.2226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855   -2.1609   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.5184   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -0.1788   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306   -1.8934   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.8267    0.0408 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6731   -1.9107    1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -2.6182    0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -3.5800    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -4.0006    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -3.8549    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -1.8681    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.9002    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.6062   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -0.1415    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.2423   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985    1.7710    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234    1.9664    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    3.3398   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681    3.5795   -1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328    5.0282   -1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.3771   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    2.0601    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    0.3073   -1.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    2.9378   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332    3.3492   -0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8596    1.5029   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8662   -1.4615   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972   -3.2247   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7587   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0699   -2.9003   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841   -0.7178    1.0573 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
M  END

1186
  Mrv0541 02231215182D          

 24 27  0  0  1  0            999 V2000
    2.3661    2.3349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705    1.0944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5455   -2.3016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -0.1774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5572    0.2351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0920    0.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.1002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8296    1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -0.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -1.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -1.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5572   -1.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2897    1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -2.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920   -1.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8797   -1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993    2.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296   -2.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853   -2.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0184    2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.5118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314    0.5608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 22  1  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  0  0  0  0
  3 15  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4 23  1  6  0  0  0
  5  9  1  0  0  0  0
  5 24  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  1  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  2  0  0  0  0
 12 15  1  0  0  0  0
 13 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015317

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CSC)CN2CCC

> <INCHI_IDENTIFIER>
InChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,18-/m1/s1

> <INCHI_KEY>
YEHCICAEULNIGD-MZMPZRCHSA-N

> <FORMULA>
C19H26N2S

> <MOLECULAR_WEIGHT>
314.488

> <EXACT_MASS>
314.181669532

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
38.398018696635305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
4.225289858

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.350344088893937

> <JCHEM_PKA_STRONGEST_BASIC>
9.486434456169016

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
97.0167

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.84e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pergolide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015317
     RDKit          3D
Pergolide
 48 51  0  0  0  0  0  0  0  0999 V2000
    3.5570   -2.7511    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -3.2492    0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -2.2874    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.2202    0.1898 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.2558    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963    1.1180   -0.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4434    2.0900    0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753    3.8002    0.2252 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    3.9919   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795    1.5609   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6291    0.4757   -0.6949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0581    0.8384   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250    2.1445   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    2.3310   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071    1.2959   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3318   -0.0005   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -1.2225   -0.2226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855   -2.1609   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.5184   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -0.1788   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306   -1.8934   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.8267    0.0408 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6731   -1.9107    1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -2.6182    0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -3.5800    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -4.0006    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -3.8549    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -1.8681    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.9002    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.6062   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -0.1415    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.2423   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985    1.7710    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234    1.9664    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    3.3398   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681    3.5795   -1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328    5.0282   -1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.3771   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    2.0601    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    0.3073   -1.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    2.9378   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332    3.3492   -0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8596    1.5029   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8662   -1.4615   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972   -3.2247   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7587   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0699   -2.9003   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841   -0.7178    1.0573 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1186                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.417   4.358   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       8.532   2.043   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      10.352  -4.296   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.173  -0.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.507   0.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.772   0.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.759   2.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.149   2.856   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.841  -0.331   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.173  -1.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.841  -1.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.507  -2.641   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.874   2.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.423   2.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.532  -4.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.772  -2.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.975  -2.899   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.892   4.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.149  -5.058   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.759  -4.256   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.234   5.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   5.123   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       6.111  -0.955   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       9.579   1.047   0.000  0.00  0.00           H+0
CONECT    1   14   22                                                       
CONECT    2    5    8   13                                                  
CONECT    3   15   17                                                       
CONECT    4    5    6   10   23                                             
CONECT    5    2    4    9   24                                             
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    2    7                                                       
CONECT    9    5   11                                                       
CONECT   10    4   12   16                                                  
CONECT   11    9   12   17                                                  
CONECT   12   10   11   15                                                  
CONECT   13    2   18                                                       
CONECT   14    1    7                                                       
CONECT   15    3   12   19                                                  
CONECT   16   10   20                                                       
CONECT   17    3   11                                                       
CONECT   18   13   21                                                       
CONECT   19   15   20                                                       
CONECT   20   16   19                                                       
CONECT   21   18                                                            
CONECT   22    1                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0015317
HETATM    1  C1  UNL     1       3.557  -2.751   1.011  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.168  -3.249   0.961  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.058  -2.287   1.137  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.935  -1.220   0.190  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.937  -0.256   0.355  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.696   1.118  -0.198  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.443   2.090   0.726  1.00  0.00           C  
HETATM    8  S1  UNL     1       2.275   3.800   0.225  1.00  0.00           S  
HETATM    9  C7  UNL     1       3.132   3.992  -1.382  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.279   1.561  -0.243  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.629   0.476  -0.695  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.058   0.838  -0.516  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.525   2.144  -0.430  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.900   2.331  -0.260  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.807   1.296  -0.174  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.332  -0.000  -0.261  1.00  0.00           C  
HETATM   17  N2  UNL     1      -4.873  -1.222  -0.223  1.00  0.00           N  
HETATM   18  C15 UNL     1      -3.886  -2.161  -0.363  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.662  -1.518  -0.497  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.982  -0.179  -0.428  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.231  -1.893  -0.681  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.403  -0.827   0.041  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.673  -1.911   1.694  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.027  -2.618   0.006  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.182  -3.580   1.463  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.046  -4.001   1.811  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.054  -3.855   0.012  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.174  -1.868   2.192  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.122  -2.900   1.250  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.885  -0.606  -0.135  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.198  -0.141   1.447  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.141   1.242  -1.219  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.498   1.771   0.870  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.923   1.966   1.724  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.610   3.340  -2.094  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.168   3.579  -1.224  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.133   5.028  -1.729  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.202   2.377  -1.021  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.060   2.060   0.701  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.469   0.307  -1.789  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.813   2.938  -0.500  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.233   3.349  -0.199  1.00  0.00           H  
HETATM   43  H21 UNL     1      -5.860   1.503  -0.042  1.00  0.00           H  
HETATM   44  H22 UNL     1      -5.866  -1.461  -0.109  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.997  -3.225  -0.373  1.00  0.00           H  
HETATM   46  H24 UNL     1      -0.979  -1.759  -1.765  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.070  -2.900  -0.324  1.00  0.00           H  
HETATM   48  H26 UNL     1      -0.884  -0.718   1.057  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   22
CONECT    5    6   30   31
CONECT    6    7   10   32
CONECT    7    8   33   34
CONECT    8    9
CONECT    9   35   36   37
CONECT   10   11   38   39
CONECT   11   12   22   40
CONECT   12   13   13   20
CONECT   13   14   41
CONECT   14   15   15   42
CONECT   15   16   43
CONECT   16   17   20   20
CONECT   17   18   44
CONECT   18   19   19   45
CONECT   19   20   21
CONECT   21   22   46   47
CONECT   22   48
END

HMDB0015317
     RDKit          3D
Pergolide
 48 51  0  0  0  0  0  0  0  0999 V2000
    3.5570   -2.7511    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -3.2492    0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -2.2874    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.2202    0.1898 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9371   -0.2558    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963    1.1180   -0.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4434    2.0900    0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753    3.8002    0.2252 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    3.9919   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795    1.5609   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6291    0.4757   -0.6949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0581    0.8384   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250    2.1445   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    2.3310   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071    1.2959   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3318   -0.0005   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -1.2225   -0.2226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855   -2.1609   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.5184   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -0.1788   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306   -1.8934   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.8267    0.0408 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6731   -1.9107    1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -2.6182    0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -3.5800    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -4.0006    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -3.8549    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -1.8681    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.9002    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.6062   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -0.1415    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    1.2423   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985    1.7710    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234    1.9664    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    3.3398   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681    3.5795   -1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328    5.0282   -1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.3771   -1.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    2.0601    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    0.3073   -1.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    2.9378   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332    3.3492   -0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8596    1.5029   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8662   -1.4615   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972   -3.2247   -0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7587   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0699   -2.9003   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841   -0.7178    1.0573 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pergolida	ChEBI
Pergolidum	ChEBI
Permax	Kegg
Pergolide methanesulfonate	HMDB
Athena brand OF pergolide mesylate	HMDB
Elanco brand OF pergolide mesylate	HMDB
Mesylate, pergolide	HMDB
Pergolide mesylate	HMDB
Celance	HMDB
Lilly brand OF pergolide	HMDB
Parkotil	HMDB
Draxis brand OF pergolide mesylate	HMDB
Lilly brand OF pergolide mesylate	HMDB
Pharken	HMDB

Chemical Formula

C₁₉H₂₆N₂S

Average Molecular Weight

314.488

Monoisotopic Molecular Weight

314.181669532

IUPAC Name

(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

Traditional Name

pergolide

CAS Registry Number

66104-22-1

SMILES

[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CSC)CN2CCC

InChI Identifier

InChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,18-/m1/s1

InChI Key

YEHCICAEULNIGD-MZMPZRCHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Ergoline skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Indole
Indole or derivatives
Alkaloid or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Sulfenyl compound
Dialkylthioether
Azacycle
Thioether
Amine
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:63617 )
methyl sulfide (CHEBI:63617 )
diamine (CHEBI:63617 )

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

Membrane (HMDB: HMDB0015317)

Source

Exogenous

Exogenous (HMDB: HMDB0015317)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antiparkinson drug (HMDB: HMDB0015317)

Dopamine agonist (HMDB: HMDB0015317)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00058 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	177.9	30932474
[M+H]+	Not Available	177.396	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001025

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	4.17	ALOGPS
logP	4.23	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	17.35	ChemAxon
pKa (Strongest Basic)	9.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.02 m³·mol⁻¹	ChemAxon
Polarizability	38.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.866	31661259
DarkChem	[M-H]-	174.649	31661259
DeepCCS	[M-2H]-	210.465	30932474
DeepCCS	[M+Na]+	185.24	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	173.3	32859911
AllCCS	[M+NH4]+	179.1	32859911
AllCCS	[M+Na]+	179.9	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	181.2	32859911
AllCCS	[M+HCOO]-	181.2	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.	5.36 minutes	32390414
Predicted by Siyang on May 30, 2022	11.609 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1693.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	238.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	405.8 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	441.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1022.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	431.7 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	1225.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	273.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	372.5 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pergolide	[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CSC)CN2CCC	4046.4	Standard polar	33892256
Pergolide	[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CSC)CN2CCC	2950.7	Standard non polar	33892256
Pergolide	[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CSC)CN2CCC	2985.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pergolide,1TMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	2659.5	Semi standard non polar	33892256
Pergolide,1TMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	2889.3	Standard non polar	33892256
Pergolide,1TMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	3436.3	Standard polar	33892256
Pergolide,1TBDMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	2851.6	Semi standard non polar	33892256
Pergolide,1TBDMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	3123.4	Standard non polar	33892256
Pergolide,1TBDMS,isomer #1	CCCN1C[C@H](CSC)C[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	3518.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pergolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mk-2790000000-1b8ba54d5d2568dccfc8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pergolide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide LC-ESI-QTOF , positive-QTOF	splash10-014i-0009000000-2ad79ab70c752608fcb3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide LC-ESI-QTOF , positive-QTOF	splash10-066r-0679000000-884687417c70aa3885ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide LC-ESI-QTOF , positive-QTOF	splash10-0gbc-0910000000-9ab47ed0d8af7d82612b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide , positive-QTOF	splash10-014i-0329000000-1f96cb9d349909c64088	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide 35V, Positive-QTOF	splash10-066r-0965000000-a0878944c42cf3c2bb28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide 10V, Positive-QTOF	splash10-014i-0009000000-7411c2d1bd178ae44431	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide 20V, Positive-QTOF	splash10-066r-0569000000-c11a58bee8ef4331cc99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pergolide 40V, Positive-QTOF	splash10-0gbc-0910000000-9ab47ed0d8af7d82612b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 10V, Positive-QTOF	splash10-014i-1049000000-c6819e3f2395e229289a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 20V, Positive-QTOF	splash10-014l-5193000000-1862aa31561fa2c8ca19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 40V, Positive-QTOF	splash10-0006-9630000000-5bee80e04ab9297e67e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 10V, Negative-QTOF	splash10-03dj-6059000000-275f5f6d9ede2d7e8a42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 20V, Negative-QTOF	splash10-0002-9044000000-e0318035317dbb8823a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 40V, Negative-QTOF	splash10-0002-9110000000-89438865cc7ce104b644	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 10V, Positive-QTOF	splash10-014i-0009000000-ed1849c1b4a4c4ed7ddf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 20V, Positive-QTOF	splash10-014i-0009000000-d8500b18d37ff1636280	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 40V, Positive-QTOF	splash10-03xr-6930000000-46296dfe5d34e43b2759	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 10V, Negative-QTOF	splash10-03di-0009000000-a594a3c3e856a1b44d62	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 20V, Negative-QTOF	splash10-03di-0009000000-b3447a9a81dcc08a70c5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergolide 40V, Negative-QTOF	splash10-07vi-1094000000-f4b2d4c92aa76ad840a9	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 DB01186	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01186	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

DB01186

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

43503

KEGG Compound ID

C07425

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pergolide

METLIN ID

Not Available

PubChem Compound

47811

PDB ID

Not Available

ChEBI ID

63617

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

Breitenstein C, Korsukewitz C, Floel A, Kretzschmar T, Diederich K, Knecht S: Tonic dopaminergic stimulation impairs associative learning in healthy subjects. Neuropsychopharmacology. 2006 Nov;31(11):2552-64. Epub 2006 Jul 26. [PubMed:16880771 ]
Schade R, Andersohn F, Suissa S, Haverkamp W, Garbe E: Dopamine agonists and the risk of cardiac-valve regurgitation. N Engl J Med. 2007 Jan 4;356(1):29-38. [PubMed:17202453 ]

Only showing the first 10 proteins. There are 19 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

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 ]
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 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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 ]
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

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

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Fuller RW, Hemrick-Luecke SK, Perry KW, Toomey RE: Pergolide elevation of MHPG sulphate concentration in rat hypothalamus blocked by spiperone and mimicked by other dopamine agonists. J Pharm Pharmacol. 1985 Apr;37(4):268-70. [PubMed:2860228 ]
Huettl P, Gerhardt GA, Browning MD, Masserano JM: Effects of dopamine receptor agonists and antagonists on catecholamine release in bovine chromaffin cells. J Pharmacol Exp Ther. 1991 May;257(2):567-74. [PubMed:1674528 ]
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 ]
Linazasoro G, Obeso JA, Gomez JC, Martinez M, Antonini A, Leenders KL: Modification of dopamine D2 receptor activity by pergolide in Parkinson's disease: an in vivo study by PET. Clin Neuropharmacol. 1999 Sep-Oct;22(5):277-80. [PubMed:10516878 ]
Mehta MA, Riedel WJ: Dopaminergic enhancement of cognitive function. Curr Pharm Des. 2006;12(20):2487-500. [PubMed:16842172 ]
Paturle L, Fage D, Fourrier O, Vernier P, Feuerstein C, Demenge P, Scatton B: Cortical ablation fails to influence striatal dopamine target cell supersensitivity induced by nigrostriatal denervation in the rat. Brain Res. 1987 Feb 3;402(2):383-6. [PubMed:3828803 ]

Enzyme Details

6. 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

7. 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

8. 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

9. 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 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 2A

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. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

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 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Showing metabocard for Pergolide (HMDB0015317)

MOL for HMDB0015317 (Pergolide)

3D MOL for HMDB0015317 (Pergolide)

3D SDF for HMDB0015317 (Pergolide)

3D-SDF for HMDB0015317 (Pergolide)

PDB for HMDB0015317 (Pergolide)

3D PDB for HMDB0015317 (Pergolide)

SMILES for HMDB0015317 (Pergolide)

INCHI for HMDB0015317 (Pergolide)

Structure for HMDB0015317 (Pergolide)

3D Structure for HMDB0015317 (Pergolide)

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

References

References

References

References

References

References

References

References