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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (2) Show 13 proteins XML

enzymes (11)transporters (2) Show 13 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014834

Secondary Accession Numbers

HMDB14834

Metabolite Identification

Common Name

Ergotamine

Description

Ergotamine is only found in individuals that have used or taken this drug. It is a vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders. [PubChem]Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT_1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT_1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

Structure

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

696
  Mrv0541 02231214562D          

 45 52  0  0  1  0            999 V2000
    3.6245    0.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811    0.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828    3.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    1.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4339   -1.3764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    2.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860    1.5939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -0.1361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -1.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3230   -4.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    1.7378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5335    1.2554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0622    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3689    2.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1959    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    0.2737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6997    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    0.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1214    2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2591   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -1.3708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3347   -2.2359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1468   -0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044    3.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6202   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6202   -3.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492   -3.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3347   -3.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0672   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9569    3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    4.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -4.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6572   -4.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -3.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0399    4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    4.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -4.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3706    5.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287    1.0918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -1.9102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 17  1  0  0  0  0
 12  2  1  6  0  0  0
  3 18  2  0  0  0  0
  4 19  2  0  0  0  0
  5 24  2  0  0  0  0
  6 11  1  0  0  0  0
  6 15  1  0  0  0  0
  6 18  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  0  0  0  0
  7 19  1  0  0  0  0
 17  8  1  6  0  0  0
  8 24  1  0  0  0  0
  9 23  1  0  0  0  0
  9 26  1  0  0  0  0
  9 33  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 44  1  1  0  0  0
 13 16  1  0  0  0  0
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 14 20  1  6  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  1  0  0  0  0
 20 25  1  0  0  0  0
 22 24  1  1  0  0  0
 22 26  1  0  0  0  0
 22 29  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 23 45  1  1  0  0  0
 25 34  2  0  0  0  0
 25 35  1  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 30 32  2  0  0  0  0
 30 38  1  0  0  0  0
 31 32  1  0  0  0  0
 31 37  2  0  0  0  0
 32 36  1  0  0  0  0
 34 40  1  0  0  0  0
 35 41  2  0  0  0  0
 36 39  2  0  0  0  0
 38 42  2  0  0  0  0
 39 42  1  0  0  0  0
 40 43  2  0  0  0  0
 41 43  1  0  0  0  0
M  END

HMDB0014834
     RDKit          3D
Ergotamine
 78 85  0  0  0  0  0  0  0  0999 V2000
   -3.4722    3.4042    1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818    3.0521   -0.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378    2.5560   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110    1.3256    0.7880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3583    0.5971    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.4514    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412    0.0454   -0.7612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -0.6600   -1.0523 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1470   -1.1039   -2.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.7250   -0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -1.8471   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0061   -2.1331    1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -2.9669   -0.8280 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8770   -4.3225   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -4.8930    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -4.3360   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -2.9807   -0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5107   -1.7608   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7199   -1.7501   -0.8910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105   -0.4890   -0.3274 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3215    0.0344    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.3203    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    1.3046    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    2.5198    2.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446    3.7365    2.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5952    3.7331    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960    2.5407    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3902   -0.6080   -0.4029 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332    0.2549   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.4939   -0.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    0.4501    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    0.8146   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0149   -0.1180   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8686   -1.4654    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9910   -2.2671   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2078   -1.7381   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3703   -0.3886   -0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3175    0.4843   -1.1134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8145    1.7443   -1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4482    1.6846   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364    0.3734   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3898    2.6656   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0084    2.1126   -0.7250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0025    2.5677    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    3.5821    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    4.3339    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    2.2919   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750    3.3657    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633    1.7165    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    0.1789   -1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -0.8000   -3.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143   -0.6134   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534   -2.1987   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795   -1.8578    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -2.8374   -1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -4.2773    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -4.9666   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225   -4.4441    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -5.9887    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0345   -4.3588    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -4.9134   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1569   -0.7249    1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137    0.2112    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    0.3744    2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0249    2.4405    3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    4.6539    2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    4.6972    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    2.5798    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.5155    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201   -1.8325    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8647   -3.3177    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0885   -2.3528   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5121    3.3192    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    2.0467   -1.8238 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  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  8 10  1  0
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 11 12  1  1
 11 13  1  0
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 21 22  1  0
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 29 30  2  0
  4 31  1  0
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 29  8  1  0
 43 32  1  0
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 17 13  1  0
 27 22  1  0
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 13 55  1  6
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 31 70  1  0
 34 71  1  0
 35 72  1  0
 36 73  1  0
 38 74  1  0
 39 75  1  0
 42 76  1  0
 42 77  1  0
 43 78  1  6
M  END

696
  Mrv0541 02231214562D          

 45 52  0  0  1  0            999 V2000
    3.6245    0.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811    0.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828    3.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    1.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4339   -1.3764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    2.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860    1.5939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -0.1361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -1.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3230   -4.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    1.7378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5335    1.2554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0622    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3689    2.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1959    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    0.2737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6997    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    0.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1214    2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2591   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -1.3708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3347   -2.2359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1468   -0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044    3.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6202   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6202   -3.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492   -3.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3347   -3.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0672   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9569    3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    4.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -4.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6572   -4.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -3.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0399    4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    4.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -4.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3706    5.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287    1.0918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -1.9102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 17  1  0  0  0  0
 12  2  1  6  0  0  0
  3 18  2  0  0  0  0
  4 19  2  0  0  0  0
  5 24  2  0  0  0  0
  6 11  1  0  0  0  0
  6 15  1  0  0  0  0
  6 18  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  0  0  0  0
  7 19  1  0  0  0  0
 17  8  1  6  0  0  0
  8 24  1  0  0  0  0
  9 23  1  0  0  0  0
  9 26  1  0  0  0  0
  9 33  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 44  1  1  0  0  0
 13 16  1  0  0  0  0
 14 18  1  0  0  0  0
 14 20  1  6  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 21  1  0  0  0  0
 20 25  1  0  0  0  0
 22 24  1  1  0  0  0
 22 26  1  0  0  0  0
 22 29  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 23 45  1  1  0  0  0
 25 34  2  0  0  0  0
 25 35  1  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 30 32  2  0  0  0  0
 30 38  1  0  0  0  0
 31 32  1  0  0  0  0
 31 37  2  0  0  0  0
 32 36  1  0  0  0  0
 34 40  1  0  0  0  0
 35 41  2  0  0  0  0
 36 39  2  0  0  0  0
 38 42  2  0  0  0  0
 39 42  1  0  0  0  0
 40 43  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014834

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

> <INCHI_KEY>
XCGSFFUVFURLIX-VFGNJEKYSA-N

> <FORMULA>
C33H35N5O5

> <MOLECULAR_WEIGHT>
581.6615

> <EXACT_MASS>
581.263819255

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
61.68506242853522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.597697310346601

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.635502175693672

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.695263245586666

> <JCHEM_PKA_STRONGEST_BASIC>
7.780484014775068

> <JCHEM_POLAR_SURFACE_AREA>
118.20999999999998

> <JCHEM_REFRACTIVITY>
160.16779999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ergomar

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014834
     RDKit          3D
Ergotamine
 78 85  0  0  0  0  0  0  0  0999 V2000
   -3.4722    3.4042    1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818    3.0521   -0.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378    2.5560   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110    1.3256    0.7880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3583    0.5971    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.4514    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412    0.0454   -0.7612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -0.6600   -1.0523 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1470   -1.1039   -2.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.7250   -0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -1.8471   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0061   -2.1331    1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -2.9669   -0.8280 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.9810   -4.8930    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -4.3360   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7199   -1.7501   -0.8910 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3215    0.0344    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.3203    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    1.3046    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    2.5198    2.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446    3.7365    2.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5952    3.7331    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960    2.5407    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3902   -0.6080   -0.4029 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332    0.2549   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.4939   -0.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    0.4501    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    0.8146   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0149   -0.1180   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8686   -1.4654    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9910   -2.2671   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2078   -1.7381   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3703   -0.3886   -0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3175    0.4843   -1.1134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8145    1.7443   -1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4482    1.6846   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364    0.3734   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3898    2.6656   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0084    2.1126   -0.7250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0025    2.5677    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    3.5821    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    4.3339    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    2.2919   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750    3.3657    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633    1.7165    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    0.1789   -1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -0.8000   -3.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143   -0.6134   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534   -2.1987   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795   -1.8578    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -2.8374   -1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -4.2773    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -4.9666   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225   -4.4441    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -5.9887    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0345   -4.3588    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -4.9134   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1595    0.2290   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569   -0.7249    1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137    0.2112    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    0.3744    2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0249    2.4405    3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    4.6539    2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    4.6972    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    2.5798    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.5155    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201   -1.8325    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8647   -3.3177    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0885   -2.3528   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2885    0.2046   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2974    2.6746   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5008    3.3855   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    3.3192    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    2.0467   -1.8238 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  2  0
  5  7  1  0
  8  7  1  1
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  8 10  1  0
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 15 16  1  0
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 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
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 24 25  2  0
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  4 31  1  0
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 32 33  1  0
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 37 38  1  0
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 29  8  1  0
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 41 33  1  0
 17 13  1  0
 27 22  1  0
 41 37  2  0
  1 44  1  0
  1 45  1  0
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  3 47  1  0
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 38 74  1  0
 39 75  1  0
 42 76  1  0
 42 77  1  0
 43 78  1  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 696                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.766   0.822   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.191   1.712   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.061   6.940   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.557   2.003   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.277  -2.569   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.502   4.776   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.001   2.975   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.601  -0.254   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.716  -2.570   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      15.536  -8.909   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.347   3.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.596   2.343   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.849   2.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.155   4.507   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.099   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   4.247   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.265   0.511   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.906   5.408   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.026   1.839   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.560   5.139   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.950  -0.997   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.944  -2.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.691  -4.174   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.607  -1.794   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.715   6.671   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.333  -1.757   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.358  -4.944   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.025  -4.944   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.956  -4.163   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.358  -6.484   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.025  -6.484   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.691  -7.254   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.059  -1.815   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.120   7.303   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.466   7.572   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.716  -8.858   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.160  -7.511   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.956  -7.264   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.333  -9.670   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.274   8.835   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.621   9.104   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.944  -8.868   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.025   9.736   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0       5.094   2.038   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      14.763  -3.566   0.000  0.00  0.00           H+0
CONECT    1   12   17                                                       
CONECT    2   12                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5   24                                                            
CONECT    6   11   15   18                                                  
CONECT    7   12   14   19                                                  
CONECT    8   17   24                                                       
CONECT    9   23   26   33                                                  
CONECT   10   36   37                                                       
CONECT   11    6   12   13   44                                             
CONECT   12    1    2    7   11                                             
CONECT   13   11   16                                                       
CONECT   14    7   18   20                                                  
CONECT   15    6   16                                                       
CONECT   16   13   15                                                       
CONECT   17    1    8   19   21                                             
CONECT   18    3    6   14                                                  
CONECT   19    4    7   17                                                  
CONECT   20   14   25                                                       
CONECT   21   17                                                            
CONECT   22   24   26   29                                                  
CONECT   23    9   27   28   45                                             
CONECT   24    5    8   22                                                  
CONECT   25   20   34   35                                                  
CONECT   26    9   22                                                       
CONECT   27   23   29   30                                                  
CONECT   28   23   31                                                       
CONECT   29   22   27                                                       
CONECT   30   27   32   38                                                  
CONECT   31   28   32   37                                                  
CONECT   32   30   31   36                                                  
CONECT   33    9                                                            
CONECT   34   25   40                                                       
CONECT   35   25   41                                                       
CONECT   36   10   32   39                                                  
CONECT   37   10   31                                                       
CONECT   38   30   42                                                       
CONECT   39   36   42                                                       
CONECT   40   34   43                                                       
CONECT   41   35   43                                                       
CONECT   42   38   39                                                       
CONECT   43   40   41                                                       
CONECT   44   11                                                            
CONECT   45   23                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  104    0
END

COMPND    HMDB0014834
HETATM    1  C1  UNL     1      -3.472   3.404   1.224  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.082   3.052  -0.107  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.738   2.556  -0.104  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.611   1.326   0.788  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.358   0.597   0.510  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.474   0.451   1.431  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.041   0.045  -0.761  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.162  -0.660  -1.052  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.147  -1.104  -2.496  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.412  -1.725  -0.207  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.766  -1.847  -0.020  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.006  -2.133   1.320  1.00  0.00           O  
HETATM   13  C8  UNL     1       3.383  -2.967  -0.828  1.00  0.00           C  
HETATM   14  C9  UNL     1       2.877  -4.322  -0.361  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.981  -4.893   0.500  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.212  -4.336  -0.179  1.00  0.00           C  
HETATM   17  N3  UNL     1       4.806  -2.981  -0.520  1.00  0.00           N  
HETATM   18  C12 UNL     1       5.511  -1.761  -0.597  1.00  0.00           C  
HETATM   19  O4  UNL     1       6.720  -1.750  -0.891  1.00  0.00           O  
HETATM   20  C13 UNL     1       4.810  -0.489  -0.327  1.00  0.00           C  
HETATM   21  C14 UNL     1       5.322   0.034   0.988  1.00  0.00           C  
HETATM   22  C15 UNL     1       4.681   1.320   1.359  1.00  0.00           C  
HETATM   23  C16 UNL     1       3.529   1.305   2.112  1.00  0.00           C  
HETATM   24  C17 UNL     1       2.926   2.520   2.459  1.00  0.00           C  
HETATM   25  C18 UNL     1       3.445   3.737   2.073  1.00  0.00           C  
HETATM   26  C19 UNL     1       4.595   3.733   1.321  1.00  0.00           C  
HETATM   27  C20 UNL     1       5.196   2.541   0.974  1.00  0.00           C  
HETATM   28  N4  UNL     1       3.390  -0.608  -0.403  1.00  0.00           N  
HETATM   29  C21 UNL     1       2.333   0.255  -0.796  1.00  0.00           C  
HETATM   30  O5  UNL     1       2.363   1.494  -0.906  1.00  0.00           O  
HETATM   31  C22 UNL     1      -2.822   0.450   0.605  1.00  0.00           C  
HETATM   32  C23 UNL     1      -3.865   0.815  -0.063  1.00  0.00           C  
HETATM   33  C24 UNL     1      -5.015  -0.118  -0.194  1.00  0.00           C  
HETATM   34  C25 UNL     1      -4.869  -1.465   0.032  1.00  0.00           C  
HETATM   35  C26 UNL     1      -5.991  -2.267  -0.138  1.00  0.00           C  
HETATM   36  C27 UNL     1      -7.208  -1.738  -0.520  1.00  0.00           C  
HETATM   37  C28 UNL     1      -7.370  -0.389  -0.750  1.00  0.00           C  
HETATM   38  N5  UNL     1      -8.317   0.484  -1.113  1.00  0.00           N  
HETATM   39  C29 UNL     1      -7.814   1.744  -1.163  1.00  0.00           C  
HETATM   40  C30 UNL     1      -6.448   1.685  -0.808  1.00  0.00           C  
HETATM   41  C31 UNL     1      -6.236   0.373  -0.571  1.00  0.00           C  
HETATM   42  C32 UNL     1      -5.390   2.666  -0.654  1.00  0.00           C  
HETATM   43  C33 UNL     1      -4.008   2.113  -0.725  1.00  0.00           C  
HETATM   44  H1  UNL     1      -4.002   2.568   1.739  1.00  0.00           H  
HETATM   45  H2  UNL     1      -2.546   3.582   1.819  1.00  0.00           H  
HETATM   46  H3  UNL     1      -4.062   4.334   1.257  1.00  0.00           H  
HETATM   47  H4  UNL     1      -1.388   2.292  -1.123  1.00  0.00           H  
HETATM   48  H5  UNL     1      -1.075   3.366   0.263  1.00  0.00           H  
HETATM   49  H6  UNL     1      -1.563   1.717   1.823  1.00  0.00           H  
HETATM   50  H7  UNL     1      -0.751   0.179  -1.511  1.00  0.00           H  
HETATM   51  H8  UNL     1       2.077  -0.800  -3.031  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.314  -0.613  -3.067  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.953  -2.199  -2.606  1.00  0.00           H  
HETATM   54  H11 UNL     1       2.280  -1.858   1.913  1.00  0.00           H  
HETATM   55  H12 UNL     1       3.288  -2.837  -1.911  1.00  0.00           H  
HETATM   56  H13 UNL     1       1.910  -4.277   0.143  1.00  0.00           H  
HETATM   57  H14 UNL     1       2.772  -4.967  -1.258  1.00  0.00           H  
HETATM   58  H15 UNL     1       3.922  -4.444   1.516  1.00  0.00           H  
HETATM   59  H16 UNL     1       3.974  -5.989   0.494  1.00  0.00           H  
HETATM   60  H17 UNL     1       6.035  -4.359   0.563  1.00  0.00           H  
HETATM   61  H18 UNL     1       5.531  -4.913  -1.054  1.00  0.00           H  
HETATM   62  H19 UNL     1       5.160   0.229  -1.126  1.00  0.00           H  
HETATM   63  H20 UNL     1       5.157  -0.725   1.798  1.00  0.00           H  
HETATM   64  H21 UNL     1       6.414   0.211   0.976  1.00  0.00           H  
HETATM   65  H22 UNL     1       3.082   0.374   2.440  1.00  0.00           H  
HETATM   66  H23 UNL     1       2.025   2.441   3.051  1.00  0.00           H  
HETATM   67  H24 UNL     1       2.945   4.654   2.363  1.00  0.00           H  
HETATM   68  H25 UNL     1       4.991   4.697   1.024  1.00  0.00           H  
HETATM   69  H26 UNL     1       6.110   2.580   0.375  1.00  0.00           H  
HETATM   70  H27 UNL     1      -2.718  -0.515   1.101  1.00  0.00           H  
HETATM   71  H28 UNL     1      -3.920  -1.832   0.317  1.00  0.00           H  
HETATM   72  H29 UNL     1      -5.865  -3.318   0.041  1.00  0.00           H  
HETATM   73  H30 UNL     1      -8.088  -2.353  -0.656  1.00  0.00           H  
HETATM   74  H31 UNL     1      -9.289   0.205  -1.321  1.00  0.00           H  
HETATM   75  H32 UNL     1      -8.297   2.675  -1.416  1.00  0.00           H  
HETATM   76  H33 UNL     1      -5.501   3.385  -1.528  1.00  0.00           H  
HETATM   77  H34 UNL     1      -5.512   3.319   0.242  1.00  0.00           H  
HETATM   78  H35 UNL     1      -3.752   2.047  -1.824  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   43
CONECT    3    4   47   48
CONECT    4    5   31   49
CONECT    5    6    6    7
CONECT    7    8   50
CONECT    8    9   10   29
CONECT    9   51   52   53
CONECT   10   11
CONECT   11   12   13   28
CONECT   12   54
CONECT   13   14   17   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   60   61
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   28   62
CONECT   21   22   63   64
CONECT   22   23   23   27
CONECT   23   24   65
CONECT   24   25   25   66
CONECT   25   26   67
CONECT   26   27   27   68
CONECT   27   69
CONECT   28   29
CONECT   29   30   30
CONECT   31   32   32   70
CONECT   32   33   43
CONECT   33   34   34   41
CONECT   34   35   71
CONECT   35   36   36   72
CONECT   36   37   73
CONECT   37   38   41   41
CONECT   38   39   74
CONECT   39   40   40   75
CONECT   40   41   42
CONECT   42   43   76   77
CONECT   43   78
END

HMDB0014834
     RDKit          3D
Ergotamine
 78 85  0  0  0  0  0  0  0  0999 V2000
   -3.4722    3.4042    1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818    3.0521   -0.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378    2.5560   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110    1.3256    0.7880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3583    0.5971    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.4514    1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412    0.0454   -0.7612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -0.6600   -1.0523 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1470   -1.1039   -2.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.7250   -0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -1.8471   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0061   -2.1331    1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -2.9669   -0.8280 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8770   -4.3225   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -4.8930    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -4.3360   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -2.9807   -0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5107   -1.7608   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7199   -1.7501   -0.8910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105   -0.4890   -0.3274 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3215    0.0344    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.3203    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    1.3046    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    2.5198    2.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446    3.7365    2.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5952    3.7331    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960    2.5407    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3902   -0.6080   -0.4029 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332    0.2549   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.4939   -0.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    0.4501    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    0.8146   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0149   -0.1180   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8686   -1.4654    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9910   -2.2671   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2078   -1.7381   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3703   -0.3886   -0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3175    0.4843   -1.1134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8145    1.7443   -1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4482    1.6846   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2364    0.3734   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3898    2.6656   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0084    2.1126   -0.7250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0025    2.5677    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    3.5821    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    4.3339    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    2.2919   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750    3.3657    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633    1.7165    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506    0.1789   -1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -0.8000   -3.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143   -0.6134   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534   -2.1987   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795   -1.8578    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -2.8374   -1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -4.2773    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -4.9666   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225   -4.4441    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -5.9887    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0345   -4.3588    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5311   -4.9134   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1595    0.2290   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569   -0.7249    1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137    0.2112    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    0.3744    2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0249    2.4405    3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    4.6539    2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9910    4.6972    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    2.5798    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.5155    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201   -1.8325    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8647   -3.3177    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0885   -2.3528   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2885    0.2046   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2974    2.6746   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5008    3.3855   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    3.3192    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7516    2.0467   -1.8238 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  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 20 28  1  0
 28 29  1  0
 29 30  2  0
  4 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 43  2  1  0
 29  8  1  0
 43 32  1  0
 28 11  1  0
 41 33  1  0
 17 13  1  0
 27 22  1  0
 41 37  2  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  1
  7 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 12 54  1  0
 13 55  1  6
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 20 62  1  6
 21 63  1  0
 21 64  1  0
 23 65  1  0
 24 66  1  0
 25 67  1  0
 26 68  1  0
 27 69  1  0
 31 70  1  0
 34 71  1  0
 35 72  1  0
 36 73  1  0
 38 74  1  0
 39 75  1  0
 42 76  1  0
 42 77  1  0
 43 78  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	ChEBI
12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione	ChEBI
Ergotamin	ChEBI
Ergotamina	ChEBI
Ergotaminum	ChEBI
Gynergen	ChEBI
(5'a)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	Generator
(5'Α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	Generator
12'-Hydroxy-2'-methyl-5'a-(phenylmethyl)ergotaman-3',6',18-trione	Generator
12'-Hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione	Generator
Cornutamine	HMDB
Ergotaminine	HMDB
Lingraine	HMDB
Tartrate, ergotamine	HMDB
ErgoKranit	HMDB
Ergo-kranit	HMDB
Ergotamine tartrate (2:1)	HMDB
mono, Ergodryl	HMDB
Pfizer brand OF ergotamine tartrate	HMDB
Ergo sanol	HMDB
Ergo kranit	HMDB
Ergodryl mono	HMDB
Ergomar	HMDB
Ergostat	HMDB
Ergotamine tartrate	HMDB
Krewel brand OF ergotamine tartrate	HMDB
Lotus brand OF ergotamine tartrate	HMDB
Sanofi winthrop brand OF ergotamine tartrate	HMDB

Chemical Formula

C₃₃H₃₅N₅O₅

Average Molecular Weight

581.6615

Monoisotopic Molecular Weight

581.263819255

IUPAC Name

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

Traditional Name

ergomar

CAS Registry Number

113-15-5

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O

InChI Identifier

InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

InChI Key

XCGSFFUVFURLIX-VFGNJEKYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergotamines, dihydroergotamines, and derivatives

Alternative Parents

Substituents

Ergotamine
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Oxazolidinone
Piperazine
Pyrrole
Pyrrolidine
Heteroaromatic compound
Oxazolidine
Tertiary carboxylic acid amide
Carboxamide group
Tertiary amine
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Secondary carboxylic acid amide
Orthocarboxylic acid derivative
Carboxylic acid derivative
Organoheterocyclic compound
Alkanolamine
Oxacycle
Azacycle
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

peptide ergot alkaloid (CHEBI:64318 )

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: HMDB0014834)

Process

Not Available

Role

Industrial application

Vasoconstrictor agent (HMDB: HMDB0014834)
Serotonergic agonist (HMDB: HMDB0014834)
Non-narcotic analgesic (HMDB: HMDB0014834)
Alpha-adrenergic agonist (HMDB: HMDB0014834)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	231.848	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001367

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.6	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	160.17 m³·mol⁻¹	ChemAxon
Polarizability	61.69 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	265.081	30932474
DeepCCS	[M+Na]+	238.931	30932474
AllCCS	[M+H]+	235.3	32859911
AllCCS	[M+H-H2O]+	234.3	32859911
AllCCS	[M+NH4]+	236.2	32859911
AllCCS	[M+Na]+	236.5	32859911
AllCCS	[M-H]-	216.8	32859911
AllCCS	[M+Na-2H]-	218.5	32859911
AllCCS	[M+HCOO]-	220.6	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.	5.33 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3614 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	82.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2167.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	175.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	390.0 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	433.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	569.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1088.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	507.0 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	1627.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	295.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	328.1 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	9.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ergotamine	[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O	6317.4	Standard polar	33892256
Ergotamine	[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O	4410.3	Standard non polar	33892256
Ergotamine	[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O	5456.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ergotamine,1TMS,isomer #1	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4759.5	Semi standard non polar	33892256
Ergotamine,1TMS,isomer #2	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4622.8	Semi standard non polar	33892256
Ergotamine,1TMS,isomer #3	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4694.6	Semi standard non polar	33892256
Ergotamine,2TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4639.4	Semi standard non polar	33892256
Ergotamine,2TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4731.6	Standard non polar	33892256
Ergotamine,2TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	6233.0	Standard polar	33892256
Ergotamine,2TMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4672.6	Semi standard non polar	33892256
Ergotamine,2TMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4660.1	Standard non polar	33892256
Ergotamine,2TMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	6234.2	Standard polar	33892256
Ergotamine,2TMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4573.6	Semi standard non polar	33892256
Ergotamine,2TMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4689.0	Standard non polar	33892256
Ergotamine,2TMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	6231.5	Standard polar	33892256
Ergotamine,3TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4600.6	Semi standard non polar	33892256
Ergotamine,3TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4680.6	Standard non polar	33892256
Ergotamine,3TMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	5987.9	Standard polar	33892256
Ergotamine,1TBDMS,isomer #1	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4942.8	Semi standard non polar	33892256
Ergotamine,1TBDMS,isomer #2	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4830.5	Semi standard non polar	33892256
Ergotamine,1TBDMS,isomer #3	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	4878.3	Semi standard non polar	33892256
Ergotamine,2TBDMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	5016.2	Semi standard non polar	33892256
Ergotamine,2TBDMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	5151.3	Standard non polar	33892256
Ergotamine,2TBDMS,isomer #1	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	6256.1	Standard polar	33892256
Ergotamine,2TBDMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5038.1	Semi standard non polar	33892256
Ergotamine,2TBDMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5060.0	Standard non polar	33892256
Ergotamine,2TBDMS,isomer #2	CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O[Si](C)(C)C(C)(C)C)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	6288.3	Standard polar	33892256
Ergotamine,2TBDMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	4952.8	Semi standard non polar	33892256
Ergotamine,2TBDMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5076.9	Standard non polar	33892256
Ergotamine,2TBDMS,isomer #3	CN1C[C@H](C(=O)N([C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](CC4=CC=CC=C4)N3C2=O)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	6283.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gi0-6692120000-7fabddfa08a8dd219bc3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (1 TMS) - 70eV, Positive	splash10-0g4j-9281023000-06e454bbac7ea8189ead	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS ("Ergotamine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergotamine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	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 - Ergotamine 10V, Positive-QTOF	splash10-001i-0022090000-66faf61c3242915f91f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 20V, Positive-QTOF	splash10-0uyi-0091010000-98b25c5586801771014a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 40V, Positive-QTOF	splash10-00di-4290000000-42f48d5180d5f2f5c20e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 10V, Negative-QTOF	splash10-0019-0049160000-6be92986c4d5c2bd6dad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 20V, Negative-QTOF	splash10-0aor-2196220000-c51c3bf00ec927a5631b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 40V, Negative-QTOF	splash10-0g5a-9810000000-7522033f4e775f417ffa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 10V, Positive-QTOF	splash10-001i-0000090000-34b8023f9528c85e96bc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 20V, Positive-QTOF	splash10-001i-0020190000-ec8f5848bc681f03dbe9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 40V, Positive-QTOF	splash10-00di-0090020000-c4d316e57df458ef5f72	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 10V, Negative-QTOF	splash10-001i-0000090000-7dfa0cf0a740c633816a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 20V, Negative-QTOF	splash10-001i-2100390000-8129f2d9526dbde472d8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergotamine 40V, Negative-QTOF	splash10-0fvi-9252430000-c9d112acb2b7bf8de124	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 DB00696	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00696	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

DB00696

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7930

KEGG Compound ID

C07544

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergotamine

METLIN ID

Not Available

PubChem Compound

8223

PDB ID

Not Available

ChEBI ID

64318

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

Tfelt-Hansen P, Saxena PR, Dahlof C, Pascual J, Lainez M, Henry P, Diener H, Schoenen J, Ferrari MD, Goadsby PJ: Ergotamine in the acute treatment of migraine: a review and European consensus. Brain. 2000 Jan;123 ( Pt 1):9-18. [PubMed:10611116 ]
Schardl CL, Panaccione DG, Tudzynski P: Ergot alkaloids--biology and molecular biology. Alkaloids Chem Biol. 2006;63:45-86. [PubMed:17133714 ]

Only showing the first 10 proteins. There are 13 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

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

Enzyme Details

2. Cytochrome P450 1A2

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

References

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

Enzyme Details

3. Alpha-2A adrenergic receptor

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

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [PubMed:18066532 ]

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

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

Verhoeff NP, Visser WH, Ferrari MD, Saxena PR, van Royen EA: Dopamine D2-receptor imaging with 123I-iodobenzamide SPECT in migraine patients abusing ergotamine: does ergotamine cross the blood brain barrier? Cephalalgia. 1993 Oct;13(5):325-9. [PubMed:8242725 ]
Larson BT, Samford MD, Camden JM, Piper EL, Kerley MS, Paterson JA, Turner JT: Ergovaline binding and activation of D2 dopamine receptors in GH4ZR7 cells. J Anim Sci. 1995 May;73(5):1396-400. [PubMed:7665369 ]

Enzyme Details

6. 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

Villalon CM, De Vries P, Rabelo G, Centurion D, Sanchez-Lopez A, Saxena P: Canine external carotid vasoconstriction to methysergide, ergotamine and dihydroergotamine: role of 5-HT1B/1D receptors and alpha2-adrenoceptors. Br J Pharmacol. 1999 Feb;126(3):585-94. [PubMed:10188968 ]
Willems EW, Trion M, De Vries P, Heiligers JP, Villalon CM, Saxena PR: Pharmacological evidence that alpha1-and alpha2-adrenoceptors mediate vasoconstriction of carotid arteriovenous anastomoses in anaesthetized pigs. Br J Pharmacol. 1999 Jul;127(5):1263-71. [PubMed:10455274 ]
Cohen ML, Schenck K: Contractile responses to sumatriptan and ergotamine in the rabbit saphenous vein: effect of selective 5-HT(1F) receptor agonists and PGF(2alpha). Br J Pharmacol. 2000 Oct;131(3):562-8. [PubMed:11015308 ]
Valdivia LF, Centurion D, Arulmani U, Saxena PR, Villalon CM: 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):46-53. Epub 2004 Jun 29. [PubMed:15224175 ]

Enzyme Details

7. 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

Bom AH, Heiligers JP, Saxena PR, Verdouw PD: Reduction of cephalic arteriovenous shunting by ergotamine is not mediated by 5-HT1-like or 5-HT2 receptors. Br J Pharmacol. 1989 Jun;97(2):383-90. [PubMed:2758221 ]
Panconesi A, Anselmi B, Curradi C, Perfetto F, Piluso A, Franchi G: Comparison between venoconstrictor effects of sumatriptan and ergotamine in migraine patients. Headache. 1994 Apr;34(4):194-7. [PubMed:8014033 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 1D

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:: HTR1D
Uniprot ID:: P28221
Molecular weight:: 41906.4

References

Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [PubMed:12558771 ]
Lovenberg TW, Erlander MG, Baron BM, Racke M, Slone AL, Siegel BW, Craft CM, Burns JE, Danielson PE, Sutcliffe JG: Molecular cloning and functional expression of 5-HT1E-like rat and human 5-hydroxytryptamine receptor genes. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2184-8. [PubMed:8384716 ]
Hoyer D, Lery H, Waeber C, Bruinvels AT, Nozulak J, Palacios JM: "5-HT1R" or 5-HT1D sites? Evidence for 5-HT1D binding sites in rabbit brain. Naunyn Schmiedebergs Arch Pharmacol. 1992 Sep;346(3):249-54. [PubMed:1407010 ]
Sanchez-Lopez A, Centurion D, Vazquez E, Arulmani U, Saxena PR, Villalon CM: Pharmacological profile of the 5-HT-induced inhibition of cardioaccelerator sympathetic outflow in pithed rats: correlation with 5-HT1 and putative 5-ht5A/5B receptors. Br J Pharmacol. 2003 Oct;140(4):725-35. Epub 2003 Sep 22. [PubMed:14504136 ]
Deliganis AV, Peroutka SJ: 5-Hydroxtryptamine1D receptor agonism predicts antimigraine efficacy. Headache. 1991 Apr;31(4):228-31. [PubMed:1646776 ]

Enzyme Details

9. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [PubMed:18066532 ]

Enzyme Details

10. Alpha-1B 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
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [PubMed:18066532 ]

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 ]

Enzyme Details

2. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Ergotamine (HMDB0014834)

MOL for HMDB0014834 (Ergotamine)

3D MOL for HMDB0014834 (Ergotamine)

3D SDF for HMDB0014834 (Ergotamine)

3D-SDF for HMDB0014834 (Ergotamine)

PDB for HMDB0014834 (Ergotamine)

3D PDB for HMDB0014834 (Ergotamine)

SMILES for HMDB0014834 (Ergotamine)

INCHI for HMDB0014834 (Ergotamine)

Structure for HMDB0014834 (Ergotamine)

3D Structure for HMDB0014834 (Ergotamine)

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

Transporters

References

References