IMPPAT Phytochemical information: 
2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-, methyl ester, (7S-(7R*,9S*))-

2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-, methyl ester, (7S-(7R*,9S*))-
Summary

SMILES: COC(=O)[C@@H]1C[C@]2(CC)CCCN(C2)CCc2c1[nH]c1c2cccc1
InChI: InChI=1S/C21H28N2O2/c1-3-21-10-6-11-23(14-21)12-9-16-15-7-4-5-8-18(15)22-19(16)17(13-21)20(24)25-2/h4-5,7-8,17,22H,3,6,9-14H2,1-2H3/t17-,21+/m1/s1
InChIKey: JFLTVMWSBAMWAW-UTKZUKDTSA-N
DeepSMILES: COC=O)[C@@H]C[C@]CC))CCCNC6)CCcc%11[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)CCC1CCCN(CC3)C1
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CCCN(CCC12)C3
Scaffold Graph level: C1CC2CCC3CC4CCCCC4C3CCC(C1)C2
Functional groups: COC(C)=O; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Quebrachamine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
vincadine, Vincadine
External chemical identifiers:
CID:CID_12444819; ZINC:ZINC000085982299
Chemical structure download


2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-, methyl ester, (7S-(7R*,9S*))-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 340.47
Log P RDKit 3.86
Topological polar surface area (Å2) RDKit 45.33
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-, methyl ester, (7S-(7R*,9S*))-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.84


2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-, methyl ester, (7S-(7R*,9S*))-
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 -5.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes