IMPPAT Phytochemical information: 
Vincaminoreine

Vincaminoreine
Summary

SMILES: COC(=O)[C@@H]1C[C@]2(CC)CCCN(C2)CCc2c1n(C)c1c2cccc1
InChI: InChI=1S/C22H30N2O2/c1-4-22-11-7-12-24(15-22)13-10-17-16-8-5-6-9-19(16)23(2)20(17)18(14-22)21(25)26-3/h5-6,8-9,18H,4,7,10-15H2,1-3H3/t18-,22+/m1/s1
InChIKey: AULRJVXQWYCCSG-GCJKJVERSA-N
DeepSMILES: COC=O)[C@@H]C[C@]CC))CCCNC6)CCcc%11nC)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; cn(C)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: Yohimbine-like alkaloids
Synonymous chemical names:
vincaminoreine
External chemical identifiers:
CID:CID_12444831; ZINC:ZINC000085982307
Chemical structure download


Vincaminoreine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.49
Log P RDKit 3.87
Topological polar surface area (Å2) RDKit 34.47
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
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 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
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


Vincaminoreine
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 0.77


Vincaminoreine
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 -5.77
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 No