IMPPAT Phytochemical information: 
Veratramine

Veratramine
Summary

SMILES: C[C@@H]1CN[C@H]([C@@H](C1)O)[C@H](c1ccc2c(c1C)C[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
InChI: InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1
InChIKey: MALFODICFSIXPO-KFKQDBFTSA-N
DeepSMILES: C[C@@H]CN[C@H][C@@H]C6)O))[C@H]cccccc6C))C[C@H][C@H]5CC=C[C@]6C)CC[C@@H]C6)O))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=C2CCCCC2C2Cc3cc(CC4CCCCN4)ccc3C2C1
Scaffold Graph/Node level: C1CCC(CC2CCC3C(C2)CC2C4CCCCC4CCC32)NC1
Scaffold Graph level: C1CCC(CC2CCC3C(C2)CC2C4CCCCC4CCC32)CC1
Functional groups: CNC; CO; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Fluorenes
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Lysine alkaloids|Pseudoalkaloids
NP Classifier Class: Piperidine alkaloids|Steroidal alkaloids
Synonymous chemical names:
veratramine
External chemical identifiers:
CID:CID_6070; ChEMBL:CHEMBL464724; ChEBI:CHEBI:9951; ZINC:ZINC000003875407; FDASRS:RK363YG315; SureChEMBL:SCHEMBL335680; MolPort-035-706-563
Chemical structure download


Veratramine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 409.61
Log P RDKit 4.59
Topological polar surface area (Å2) RDKit 52.49
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Veratramine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.626145


Veratramine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.72
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes