IMPPAT Phytochemical information: 
Ergotamine
Ergotamine
Summary

SMILES: O=C([C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O
InChI: 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
InChIKey: XCGSFFUVFURLIX-VFGNJEKYSA-N
DeepSMILES: O=C[C@H]CNC)[C@H]C=C6)cccccc6cC%10)c[nH]5))))))))))))))N[C@]C)O[C@@]NC5=O))[C@@H]Ccccccc6)))))))C=O)N[C@H]6CCC5))))))))O
Scaffold Graph/Node/Bond level: O=C(NC1OC2C3CCCN3C(=O)C(Cc3ccccc3)N2C1=O)C1C=C2c3cccc4[nH]cc(c34)CC2NC1
Scaffold Graph/Node level: OC(NC1OC2C3CCCN3C(O)C(CC3CCCCC3)N2C1O)C1CNC2CC3CNC4CCCC(C2C1)C34
Scaffold Graph level: CC(CC1CC2C3CCCC3C(C)C(CC3CCCCC3)C2C1C)C1CCC2CC3CCC4CCCC(C2C1)C43
Functional groups: CN(C)C; CN(C)C(C)=O; C[C@@]1(NC(C)=O)O[C@](C)(O)N(C)C1=O; cC(C)=CC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ergoline and derivatives
ClassyFire Subclass: Lysergic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Ergot alkaloids
Synonymous chemical names:
ergotamine
External chemical identifiers:
CID:8223; ChEMBL:CHEMBL442; ChEBI:64318; ZINC:ZINC000052955754; FDASRS:PR834Q503T; SureChEMBL:SCHEMBL1483
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ergotamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 581.67
Log P RDKit 1.99
Topological polar surface area (Å2) RDKit 118.21
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Ergotamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.434
Ergotamine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.68
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
Ergotamine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000219833SLC6A2800
ENSP00000258400HTR2B860
ENSP00000276198HTR2C941
ENSP00000280155ADRA2A968
ENSP00000287907HTR5A778
ENSP00000289753HTR6850
ENSP00000302150PRL818
ENSP00000306662ADRA1B930
ENSP00000307766HTR1E809
ENSP00000311032CASP3700
ENSP00000313661HTR1D998
ENSP00000316244HTR1A979
ENSP00000322924HTR1F968
ENSP00000327652883
ENSP00000354859DRD2962
ENSP00000358963HTR1B999
ENSP00000367959HTR2A977
ENSP00000368766ADRA1D973
ENSP00000369960ADRA1A914
ENSP00000373169DRD3850
ENSP00000386069ADRA2C842
ENSP00000387281ADRA2B961
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.