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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (1) Show 6 proteins XML

enzymes (5)transporters (1) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014465

Secondary Accession Numbers

HMDB14465

Metabolite Identification

Common Name

Dihydroergotamine

Description

Dihydroergotamine is only found in individuals that have used or taken this drug. It is a 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem]Two theories have been proposed to explain the efficacy of 5-HT_1D receptor agonists in migraine: 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

320
  Mrv0541 02231214362D          

 46 53  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
    4.2860    1.5939    0.0000 N   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
    7.3480   -1.3766    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
    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
    6.6203   -2.6484    0.0000 C   0  0  2  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
    2.0622    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3690    2.4147    0.0000 C   0  0  2  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
    5.8628   -1.3708    0.0000 C   0  0  2  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
    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
    3.6997    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    0.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -0.9412    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
    6.6203   -3.4734    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
    5.1468   -0.9611    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
    8.0492   -3.4734    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
    8.0672   -0.9724    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
    5.8695   -3.8915    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
    5.2044    3.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -4.7509    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    4.0564    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
    5.3706    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
    6.0512   -2.9828    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 22  2  0  0  0  0
  4 23  2  0  0  0  0
  5 28  2  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  6 23  1  0  0  0  0
  7 11  1  0  0  0  0
  7 20  1  0  0  0  0
  7 22  1  0  0  0  0
  8 14  1  0  0  0  0
  8 24  1  0  0  0  0
  8 32  1  0  0  0  0
 17  9  1  6  0  0  0
  9 28  1  0  0  0  0
 10 33  1  0  0  0  0
 10 35  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 44  1  1  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 13 26  1  0  0  0  0
 13 45  1  6  0  0  0
 14 25  1  0  0  0  0
 14 46  1  1  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 16 27  1  6  0  0  0
 17 23  1  0  0  0  0
 17 31  1  0  0  0  0
 18 19  1  0  0  0  0
 18 24  1  0  0  0  0
 18 28  1  1  0  0  0
 20 21  1  0  0  0  0
 25 30  1  0  0  0  0
 26 29  2  0  0  0  0
 26 34  1  0  0  0  0
 27 36  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 35  2  0  0  0  0
 33 37  2  0  0  0  0
 34 38  2  0  0  0  0
 36 39  2  0  0  0  0
 36 40  1  0  0  0  0
 37 38  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END

HMDB0014465
     RDKit          3D
Dihydroergotamine
 80 87  0  0  0  0  0  0  0  0999 V2000
   -4.5122    2.3464   -2.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1336    1.9189   -1.0651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634    1.4816   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044    0.7898    0.1426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9099    0.3838    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726    0.8237    0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -0.4964   -0.9682 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -0.9206   -1.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0084   -1.8535   -2.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -1.5081    0.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688   -1.0552    0.3080 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6737   -0.4154    1.5524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -2.2325    0.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3781   -3.0692    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.6783    2.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6345   -2.3720    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -1.6686    0.4697 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352   -0.6164   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5487   -0.5419   -0.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    0.4082   -0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5922    1.6858   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    2.2236   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2936    3.1077   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    3.5811   -1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5666    3.1868   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2007    2.3004    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    1.8088    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0218   -0.0961   -0.6926 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391    0.2125   -1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150    1.2020   -2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.3896    0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    0.2479    0.6106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6168   -0.6425    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3346   -1.6787    2.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -2.4362    2.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7083   -2.1930    2.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0101   -1.1589    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1330   -0.6734    0.7306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7479    0.3460   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3942    0.5105   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9275   -0.4444    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    1.4418   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    0.8776   -0.6652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1003    3.2795   -2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    2.5854   -3.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1339    2.4071   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    0.8734   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    1.4682    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -0.8492   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0478   -2.2058   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.3194   -3.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -2.6987   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -0.7310    2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -2.8042   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -4.1336    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -2.9195    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8430   -3.5235    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737   -1.7689    3.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.7482    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5966    0.6067   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    1.4735    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5086    3.4082   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454    4.2722   -2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014    3.5536   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3919    0.9849   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7742    1.5582   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    0.0883   -1.4635 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
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 31 70  1  0
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 36 75  1  0
 38 76  1  0
 39 77  1  0
 42 78  1  0
 42 79  1  0
 43 80  1  6
M  END

320
  Mrv0541 02231214362D          

 46 53  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
    4.2860    1.5939    0.0000 N   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
    7.3480   -1.3766    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
    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
    6.6203   -2.6484    0.0000 C   0  0  2  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
    2.0622    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3690    2.4147    0.0000 C   0  0  2  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
    5.8628   -1.3708    0.0000 C   0  0  2  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
    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
    3.6997    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    0.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -0.9412    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
    6.6203   -3.4734    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
    5.1468   -0.9611    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
    8.0492   -3.4734    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
    8.0672   -0.9724    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
    5.8695   -3.8915    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
    5.2044    3.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -4.7509    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    4.0564    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
    5.3706    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
    6.0512   -2.9828    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 22  2  0  0  0  0
  4 23  2  0  0  0  0
  5 28  2  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  6 23  1  0  0  0  0
  7 11  1  0  0  0  0
  7 20  1  0  0  0  0
  7 22  1  0  0  0  0
  8 14  1  0  0  0  0
  8 24  1  0  0  0  0
  8 32  1  0  0  0  0
 17  9  1  6  0  0  0
  9 28  1  0  0  0  0
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 20 21  1  0  0  0  0
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 26 29  2  0  0  0  0
 26 34  1  0  0  0  0
 27 36  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 35  2  0  0  0  0
 33 37  2  0  0  0  0
 34 38  2  0  0  0  0
 36 39  2  0  0  0  0
 36 40  1  0  0  0  0
 37 38  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014465

> <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)[C@@]4([H])C3)O[C@@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

> <INCHI_KEY>
LUZRJRNZXALNLM-JGRZULCMSA-N

> <FORMULA>
C33H37N5O5

> <MOLECULAR_WEIGHT>
583.6774

> <EXACT_MASS>
583.279469319

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
63.30311653380885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,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),9,12,14-tetraene-4-carboxamide

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.7116222909811363

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.674687752899596

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.712761266905385

> <JCHEM_PKA_STRONGEST_BASIC>
8.394791367163506

> <JCHEM_POLAR_SURFACE_AREA>
118.20999999999998

> <JCHEM_REFRACTIVITY>
159.39479999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroergotamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014465
     RDKit          3D
Dihydroergotamine
 80 87  0  0  0  0  0  0  0  0999 V2000
   -4.5122    2.3464   -2.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1336    1.9189   -1.0651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634    1.4816   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044    0.7898    0.1426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9099    0.3838    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726    0.8237    0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -0.4964   -0.9682 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -0.9206   -1.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0084   -1.8535   -2.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -1.5081    0.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688   -1.0552    0.3080 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6737   -0.4154    1.5524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -2.2325    0.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3781   -3.0692    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.6783    2.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6345   -2.3720    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5487   -0.5419   -0.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    0.4082   -0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5922    1.6858   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    2.2236   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2936    3.1077   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    3.5811   -1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5666    3.1868   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2007    2.3004    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    1.8088    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0218   -0.0961   -0.6926 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391    0.2125   -1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150    1.2020   -2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.3896    0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    0.2479    0.6106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6168   -0.6425    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3346   -1.6787    2.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -2.4362    2.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7083   -2.1930    2.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0101   -1.1589    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1330   -0.6734    0.7306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7479    0.3460   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3942    0.5105   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9275   -0.4444    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    1.4418   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    0.8776   -0.6652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1003    3.2795   -2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    2.5854   -3.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    1.5275   -2.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    2.4071   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    0.8734   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    1.4682    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -0.8492   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0478   -2.2058   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.3194   -3.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -2.6987   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -0.7310    2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -2.8042   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -4.1336    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -2.9195    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8430   -3.5235    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737   -1.7689    3.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.7482    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1574   -3.2935    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    0.6067   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    1.4735    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    2.4810   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    3.4082   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454    4.2722   -2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014    3.5536   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9722    1.9766    1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6870    1.1049    1.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -0.9519    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -1.0034   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4242    1.0697    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -1.8442    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1807   -3.2475    3.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4993   -2.8048    2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0833   -1.0197    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3919    0.9849   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4352    2.4044   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7742    1.5582   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    0.0883   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  5  6  2  0
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  8  7  1  1
  8  9  1  0
  8 10  1  0
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  4 31  1  0
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 38 76  1  0
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 42 78  1  0
 42 79  1  0
 43 80  1  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 320                                               
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       8.001   2.975   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.502   4.776   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      13.716  -2.570   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.601  -0.254   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      12.358  -4.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.691  -4.174   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.849   2.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.155   4.507   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      10.944  -2.559   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.956  -4.163   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.099   5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   4.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.906   5.408   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.026   1.839   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.333  -1.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.025  -4.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.358  -6.484   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.560   5.139   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.607  -1.794   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.691  -7.254   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.025  -6.484   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.950  -0.997   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.059  -1.815   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.716  -8.858   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.956  -7.264   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.160  -7.511   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.715   6.671   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.333  -9.670   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.944  -8.868   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.120   7.303   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.466   7.572   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.274   8.835   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.621   9.104   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      11.296  -5.568   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      14.763  -3.566   0.000  0.00  0.00           H+0
CONECT    1   12   17                                                       
CONECT    2   12                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   28                                                            
CONECT    6   12   16   23                                                  
CONECT    7   11   20   22                                                  
CONECT    8   14   24   32                                                  
CONECT    9   17   28                                                       
CONECT   10   33   35                                                       
CONECT   11    7   12   15   44                                             
CONECT   12    1    2    6   11                                             
CONECT   13   14   19   26   45                                             
CONECT   14    8   13   25   46                                             
CONECT   15   11   21                                                       
CONECT   16    6   22   27                                                  
CONECT   17    1    9   23   31                                             
CONECT   18   19   24   28                                                  
CONECT   19   13   18                                                       
CONECT   20    7   21                                                       
CONECT   21   15   20                                                       
CONECT   22    3    7   16                                                  
CONECT   23    4    6   17                                                  
CONECT   24    8   18                                                       
CONECT   25   14   30                                                       
CONECT   26   13   29   34                                                  
CONECT   27   16   36                                                       
CONECT   28    5    9   18                                                  
CONECT   29   26   30   33                                                  
CONECT   30   25   29   35                                                  
CONECT   31   17                                                            
CONECT   32    8                                                            
CONECT   33   10   29   37                                                  
CONECT   34   26   38                                                       
CONECT   35   10   30                                                       
CONECT   36   27   39   40                                                  
CONECT   37   33   38                                                       
CONECT   38   34   37                                                       
CONECT   39   36   41                                                       
CONECT   40   36   42                                                       
CONECT   41   39   43                                                       
CONECT   42   40   43                                                       
CONECT   43   41   42                                                       
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  106    0
END

COMPND    HMDB0014465
HETATM    1  C1  UNL     1      -4.512   2.346  -2.402  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.134   1.919  -1.065  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.763   1.482  -1.121  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.304   0.790   0.143  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.910   0.384   0.036  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.073   0.824   0.862  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.445  -0.496  -0.968  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.918  -0.921  -1.106  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.008  -1.853  -2.301  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.405  -1.508   0.040  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.669  -1.055   0.308  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.674  -0.415   1.552  1.00  0.00           O  
HETATM   13  C8  UNL     1       3.621  -2.233   0.342  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.378  -3.069   1.553  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.496  -2.678   2.486  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.634  -2.372   1.524  1.00  0.00           C  
HETATM   17  N3  UNL     1       4.962  -1.669   0.470  1.00  0.00           N  
HETATM   18  C12 UNL     1       5.335  -0.616  -0.394  1.00  0.00           C  
HETATM   19  O4  UNL     1       6.549  -0.542  -0.784  1.00  0.00           O  
HETATM   20  C13 UNL     1       4.374   0.408  -0.866  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.592   1.686  -0.101  1.00  0.00           C  
HETATM   22  C15 UNL     1       5.954   2.224  -0.276  1.00  0.00           C  
HETATM   23  C16 UNL     1       6.294   3.108  -1.279  1.00  0.00           C  
HETATM   24  C17 UNL     1       7.579   3.581  -1.402  1.00  0.00           C  
HETATM   25  C18 UNL     1       8.567   3.187  -0.528  1.00  0.00           C  
HETATM   26  C19 UNL     1       8.201   2.300   0.467  1.00  0.00           C  
HETATM   27  C20 UNL     1       6.921   1.809   0.616  1.00  0.00           C  
HETATM   28  N4  UNL     1       3.022  -0.096  -0.693  1.00  0.00           N  
HETATM   29  C21 UNL     1       1.839   0.213  -1.405  1.00  0.00           C  
HETATM   30  O5  UNL     1       1.615   1.202  -2.119  1.00  0.00           O  
HETATM   31  C22 UNL     1      -3.262  -0.390   0.375  1.00  0.00           C  
HETATM   32  C23 UNL     1      -4.602   0.248   0.611  1.00  0.00           C  
HETATM   33  C24 UNL     1      -5.617  -0.643   1.193  1.00  0.00           C  
HETATM   34  C25 UNL     1      -5.335  -1.679   2.085  1.00  0.00           C  
HETATM   35  C26 UNL     1      -6.407  -2.436   2.561  1.00  0.00           C  
HETATM   36  C27 UNL     1      -7.708  -2.193   2.180  1.00  0.00           C  
HETATM   37  C28 UNL     1      -8.010  -1.159   1.287  1.00  0.00           C  
HETATM   38  N5  UNL     1      -9.133  -0.673   0.731  1.00  0.00           N  
HETATM   39  C29 UNL     1      -8.748   0.346  -0.057  1.00  0.00           C  
HETATM   40  C30 UNL     1      -7.394   0.510  -0.005  1.00  0.00           C  
HETATM   41  C31 UNL     1      -6.927  -0.444   0.848  1.00  0.00           C  
HETATM   42  C32 UNL     1      -6.445   1.442  -0.648  1.00  0.00           C  
HETATM   43  C33 UNL     1      -5.043   0.878  -0.665  1.00  0.00           C  
HETATM   44  H1  UNL     1      -5.100   3.280  -2.372  1.00  0.00           H  
HETATM   45  H2  UNL     1      -3.592   2.585  -3.010  1.00  0.00           H  
HETATM   46  H3  UNL     1      -5.024   1.528  -2.940  1.00  0.00           H  
HETATM   47  H4  UNL     1      -2.134   2.407  -1.209  1.00  0.00           H  
HETATM   48  H5  UNL     1      -2.539   0.873  -2.010  1.00  0.00           H  
HETATM   49  H6  UNL     1      -2.446   1.468   1.001  1.00  0.00           H  
HETATM   50  H7  UNL     1      -1.153  -0.849  -1.642  1.00  0.00           H  
HETATM   51  H8  UNL     1       2.048  -2.206  -2.460  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.591  -1.319  -3.175  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.314  -2.699  -2.088  1.00  0.00           H  
HETATM   54  H11 UNL     1       1.868  -0.731   2.070  1.00  0.00           H  
HETATM   55  H12 UNL     1       3.551  -2.804  -0.594  1.00  0.00           H  
HETATM   56  H13 UNL     1       3.544  -4.134   1.266  1.00  0.00           H  
HETATM   57  H14 UNL     1       2.370  -2.920   1.987  1.00  0.00           H  
HETATM   58  H15 UNL     1       4.843  -3.524   3.115  1.00  0.00           H  
HETATM   59  H16 UNL     1       4.274  -1.769   3.078  1.00  0.00           H  
HETATM   60  H17 UNL     1       6.362  -1.748   2.081  1.00  0.00           H  
HETATM   61  H18 UNL     1       6.157  -3.293   1.185  1.00  0.00           H  
HETATM   62  H19 UNL     1       4.597   0.607  -1.931  1.00  0.00           H  
HETATM   63  H20 UNL     1       4.368   1.473   0.979  1.00  0.00           H  
HETATM   64  H21 UNL     1       3.877   2.481  -0.394  1.00  0.00           H  
HETATM   65  H22 UNL     1       5.509   3.408  -1.958  1.00  0.00           H  
HETATM   66  H23 UNL     1       7.845   4.272  -2.185  1.00  0.00           H  
HETATM   67  H24 UNL     1       9.601   3.554  -0.610  1.00  0.00           H  
HETATM   68  H25 UNL     1       8.972   1.977   1.169  1.00  0.00           H  
HETATM   69  H26 UNL     1       6.687   1.105   1.428  1.00  0.00           H  
HETATM   70  H27 UNL     1      -2.867  -0.952   1.221  1.00  0.00           H  
HETATM   71  H28 UNL     1      -3.256  -1.003  -0.570  1.00  0.00           H  
HETATM   72  H29 UNL     1      -4.424   1.070   1.356  1.00  0.00           H  
HETATM   73  H30 UNL     1      -4.326  -1.844   2.360  1.00  0.00           H  
HETATM   74  H31 UNL     1      -6.181  -3.248   3.260  1.00  0.00           H  
HETATM   75  H32 UNL     1      -8.499  -2.805   2.575  1.00  0.00           H  
HETATM   76  H33 UNL     1     -10.083  -1.020   0.884  1.00  0.00           H  
HETATM   77  H34 UNL     1      -9.392   0.985  -0.674  1.00  0.00           H  
HETATM   78  H35 UNL     1      -6.435   2.404  -0.101  1.00  0.00           H  
HETATM   79  H36 UNL     1      -6.774   1.558  -1.714  1.00  0.00           H  
HETATM   80  H37 UNL     1      -4.989   0.088  -1.464  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   70   71
CONECT   32   33   43   72
CONECT   33   34   34   41
CONECT   34   35   73
CONECT   35   36   36   74
CONECT   36   37   75
CONECT   37   38   41   41
CONECT   38   39   76
CONECT   39   40   40   77
CONECT   40   41   42
CONECT   42   43   78   79
CONECT   43   80
END

HMDB0014465
     RDKit          3D
Dihydroergotamine
 80 87  0  0  0  0  0  0  0  0999 V2000
   -4.5122    2.3464   -2.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1336    1.9189   -1.0651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634    1.4816   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044    0.7898    0.1426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9099    0.3838    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726    0.8237    0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -0.4964   -0.9682 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -0.9206   -1.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0084   -1.8535   -2.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -1.5081    0.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688   -1.0552    0.3080 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6737   -0.4154    1.5524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -2.2325    0.3420 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3781   -3.0692    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.6783    2.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6345   -2.3720    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -1.6686    0.4697 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352   -0.6164   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5487   -0.5419   -0.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    0.4082   -0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5922    1.6858   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    2.2236   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2936    3.1077   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    3.5811   -1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5666    3.1868   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2007    2.3004    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    1.8088    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0218   -0.0961   -0.6926 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391    0.2125   -1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150    1.2020   -2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.3896    0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    0.2479    0.6106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6168   -0.6425    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3346   -1.6787    2.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -2.4362    2.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7083   -2.1930    2.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0101   -1.1589    1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1330   -0.6734    0.7306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7479    0.3460   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3942    0.5105   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9275   -0.4444    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4446    1.4418   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    0.8776   -0.6652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1003    3.2795   -2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    2.5854   -3.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    1.5275   -2.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    2.4071   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    0.8734   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    1.4682    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -0.8492   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0478   -2.2058   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.3194   -3.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -2.6987   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -0.7310    2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -2.8042   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -4.1336    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -2.9195    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8430   -3.5235    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737   -1.7689    3.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.7482    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1574   -3.2935    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    0.6067   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    1.4735    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    2.4810   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    3.4082   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454    4.2722   -2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014    3.5536   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9722    1.9766    1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6870    1.1049    1.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -0.9519    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -1.0034   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4242    1.0697    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -1.8442    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1807   -3.2475    3.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4993   -2.8048    2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0833   -1.0197    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3919    0.9849   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4352    2.4044   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7742    1.5582   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    0.0883   -1.4635 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  1  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
 31 71  1  0
 32 72  1  1
 34 73  1  0
 35 74  1  0
 36 75  1  0
 38 76  1  0
 39 77  1  0
 42 78  1  0
 42 79  1  0
 43 80  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman	ChEBI
9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	ChEBI
9,10-Dihydroergotamine	ChEBI
Dihidroergotamina	ChEBI
Dihydroergotaminum	ChEBI
Neomigran	Kegg
9,10-Dihydro-ergotamine	HMDB
Dihydroergotamine mesylate	HMDB
Dihydroergotamine methanesulfonate	HMDB
Dihydroergotamine monomethanesulfonate	HMDB
Clavigrenin	HMDB
D Tamin retard l.u.t.	HMDB
D.H.E. 45	HMDB
DHE 45	HMDB
DHE ratiopharm	HMDB
Desitin brand OF dihydroergotamine mesylate	HMDB
Methanesulfonate, dihydroergotamine	HMDB
Orstanorm	HMDB
Shire brand OF dihydroergotamine mesylate	HMDB
Wernigeroide brand OF dihydroergotamine mesylate	HMDB
Alpharma brand OF dihydroergotamine mesylate	HMDB
Angionorm	HMDB
Anto brand OF dihydroergotamine mesylate	HMDB
DHE-puren	HMDB
Dihydroergotamine-sandoz	HMDB
Ergomimet	HMDB
IPRAD brand OF dihydroergotamine mesylate	HMDB
Ikaran	HMDB
Migranal	HMDB
Pierre fabre brand OF dihydroergotamine mesylate	HMDB
Seglor	HMDB
Xcel brand 2 OF dihydroergotamine mesylate	HMDB
CT Arzneimittel brand OF dihydroergotamine mesylate	HMDB
CT-Arzneimittel brand OF dihydroergotamine mesylate	HMDB
Agit	HMDB
DET MS	HMDB
DHE puren	HMDB
DHE-ratiopharm	HMDB
DHE45	HMDB
Dihydroergotamin al	HMDB
Dihytamin	HMDB
Erganton	HMDB
Farmasan brand OF dihydroergotamine mesylate	HMDB
Q-Pharm brand OF dihydroergotamine mesylate	HMDB
Tamik	HMDB
Verla brand OF dihydroergotamine mesylate	HMDB
Xcel brand 1 OF dihydroergotamine mesylate	HMDB
Ergotam von CT	HMDB
Aliud brand OF dihydroergotamine mesylate	HMDB
D-Tamin retard l.u.t.	HMDB
DHE-45	HMDB
Dihydergot	HMDB
Dihydroergotamine sandoz	HMDB
Ergont	HMDB
Fujisawa brand OF dihydroergotamine mesylate	HMDB
Hormosan brand OF dihydroergotamine mesylate	HMDB
Mesylate, dihydroergotamine	HMDB
Novartis brand OF dihydroergotamine mesylate	HMDB
Pharmafrid brand OF dihydroergotamine mesylate	HMDB
Q Pharm brand OF dihydroergotamine mesylate	HMDB
Sanol brand OF dihydroergotamine mesylate	HMDB
Schwarz brand OF dihydroergotamine mesylate	HMDB
Verladyn	HMDB
Ratiopharm brand OF dihydroergotamine mesylate	HMDB
Von CT, ergotam	HMDB

Chemical Formula

C₃₃H₃₇N₅O₅

Average Molecular Weight

583.6774

Monoisotopic Molecular Weight

583.279469319

IUPAC Name

(2R,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),9,12,14-tetraene-4-carboxamide

Traditional Name

dihydroergotamine

CAS Registry Number

6190-39-2

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)[C@@]4([H])C3)O[C@@]21O

InChI Identifier

InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

InChI Key

LUZRJRNZXALNLM-JGRZULCMSA-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ergot alkaloid (CHEBI:4562 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

vasoconstrictor agent (HMDB: HMDB0014465)
serotonergic agonist (HMDB: HMDB0014465)
non-narcotic analgesic (HMDB: HMDB0014465)

Biological role

serotonergic agonist (HMDB: HMDB0014465)
non-narcotic analgesic (HMDB: HMDB0014465)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.23 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	8.39	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	159.39 m³·mol⁻¹	ChemAxon
Polarizability	63.3 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]-	256.824	30932474
DeepCCS	[M+Na]+	230.647	30932474
AllCCS	[M+H]+	235.0	32859911
AllCCS	[M+H-H2O]+	234.0	32859911
AllCCS	[M+NH4]+	235.9	32859911
AllCCS	[M+Na]+	236.1	32859911
AllCCS	[M-H]-	214.1	32859911
AllCCS	[M+Na-2H]-	216.1	32859911
AllCCS	[M+HCOO]-	218.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroergotamine	[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)[C@@]4([H])C3)O[C@@]21O	5467.4	Standard polar	33892256
Dihydroergotamine	[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)[C@@]4([H])C3)O[C@@]21O	4311.6	Standard non polar	33892256
Dihydroergotamine	[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)[C@@]4([H])C3)O[C@@]21O	5400.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4713.4	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4614.2	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4701.2	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4624.3	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4804.3	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	6065.9	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4666.8	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4728.0	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	6064.5	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4589.6	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4721.6	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	6078.6	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4611.1	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	4729.3	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]21	5821.5	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4908.4	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4815.5	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	4880.9	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	4990.7	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	5241.0	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=C[NH]4)C[C@H]21	6092.5	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5034.9	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5143.9	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	6112.5	Standard polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	4963.9	Semi standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	5120.3	Standard non polar	33892256
Dihydroergotamine,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[C@@H]2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]21	6128.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr5-5891210000-f53c38352e2598f9007e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (1 TMS) - 70eV, Positive	splash10-0fdn-7491022000-6c73d0337e04ab2f6918	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS ("Dihydroergotamine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroergotamine 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 - Dihydroergotamine 10V, Positive-QTOF	splash10-001i-0022090000-bfd200952b03e8b137ff	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Positive-QTOF	splash10-0un9-0091010000-c5661ba02ab58100d046	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Positive-QTOF	splash10-004i-4590000000-dc4a0cca36e4ae6c18c5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Negative-QTOF	splash10-0019-0049160000-4fdc70b6d84db2eb175e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Negative-QTOF	splash10-03xr-2196220000-3c3fcf127102792f663c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Negative-QTOF	splash10-0g4j-9810000000-88f13186254d2bf07e89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Positive-QTOF	splash10-001i-0000090000-3abf973bfa14967f7f1d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Positive-QTOF	splash10-001i-0010290000-1037c6e147fa5f93e653	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Positive-QTOF	splash10-004i-0090010000-f5347f35594f87c4297f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 10V, Negative-QTOF	splash10-001i-0000090000-10b01aae8e192c05edc6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 20V, Negative-QTOF	splash10-001i-2100390000-475a2b73d09ae5f9c174	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroergotamine 40V, Negative-QTOF	splash10-0v03-9351430000-9c41d997e0687489c4ee	2021-09-22	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 DB00320	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00320	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

DB00320

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001724

Chemspider ID

10091

KEGG Compound ID

C07798

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydroergotamine

METLIN ID

Not Available

PubChem Compound

10531

PDB ID

Not Available

ChEBI ID

4562

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

Enzyme Details

2. 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

Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]

Enzyme Details

3. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Schaerlinger B, Hickel P, Etienne N, Guesnier L, Maroteaux L: Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. Br J Pharmacol. 2003 Sep;140(2):277-84. Epub 2003 Aug 11. [PubMed:12970106 ]

Enzyme Details

4. 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

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 ]
Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
Buzzi MG, Moskowitz MA: Evidence for 5-HT1B/1D receptors mediating the antimigraine effect of sumatriptan and dihydroergotamine. Cephalalgia. 1991 Sep;11(4):165-8. [PubMed:1660351 ]
Yu XJ, Waeber C, Castanon N, Scearce K, Hen R, Macor JE, Chauveau J, Moskowitz MA: 5-Carboxamido-tryptamine, CP-122,288 and dihydroergotamine but not sumatriptan, CP-93,129, and serotonin-5-O-carboxymethyl-glycyl -tyrosinamide block dural plasma protein extravasation in knockout mice that lack 5-hydroxytryptamine1B receptors. Mol Pharmacol. 1996 May;49(5):761-5. [PubMed:8622623 ]
Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]

Enzyme Details

5. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Lesage AS, Wouters R, Van Gompel P, Heylen L, Vanhoenacker P, Haegeman G, Luyten WH, Leysen JE: Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65. [PubMed:9605573 ]
Buzzi MG, Moskowitz MA: The trigemino-vascular system and migraine. Pathol Biol (Paris). 1992 Apr;40(4):313-7. [PubMed:1379707 ]
Buzzi MG, Dimitriadou V, Theoharides TC, Moskowitz MA: 5-Hydroxytryptamine receptor agonists for the abortive treatment of vascular headaches block mast cell, endothelial and platelet activation within the rat dura mater after trigeminal stimulation. Brain Res. 1992 Jun 26;583(1-2):137-49. [PubMed:1324091 ]
Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [PubMed:12558771 ]
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 ]
Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]

Showing metabocard for Dihydroergotamine (HMDB0014465)

MOL for HMDB0014465 (Dihydroergotamine)

3D MOL for HMDB0014465 (Dihydroergotamine)

3D SDF for HMDB0014465 (Dihydroergotamine)

3D-SDF for HMDB0014465 (Dihydroergotamine)

PDB for HMDB0014465 (Dihydroergotamine)

3D PDB for HMDB0014465 (Dihydroergotamine)

SMILES for HMDB0014465 (Dihydroergotamine)

INCHI for HMDB0014465 (Dihydroergotamine)

Structure for HMDB0014465 (Dihydroergotamine)

3D Structure for HMDB0014465 (Dihydroergotamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References