IMPPAT Phytochemical information: 
Dtxsid60911603

Dtxsid60911603
Summary

SMILES: COC(=O)[C@@]12O[C@H]([C@@]3(C1)C=CCN1[C@@H]3[C@@]3([C@@]2(O)Nc2c3cccc2)CC1)C
InChI: InChI=1S/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1
InChIKey: YOQNZWXFGROKGY-KVKBDHCBSA-N
DeepSMILES: COC=O)[C@@]O[C@H][C@@]C5)C=CCN[C@@H]6[C@@][C@@]%11O)Ncc5cccc6))))))))CC5)))))))))C
Scaffold Graph/Node/Bond level: C1=CC23COC(C2)C2Nc4ccccc4C24CCN(C1)C34
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4(CCCN5CCC21C54)CO3
Scaffold Graph level: C1CCC2C(C1)CC1C3CCC4(CCCC5CCC21C54)C3
Functional groups: COC(C)=O; COC; CC=CC; CN(C)C; cN[C@](O)(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
vincoline
External chemical identifiers:
CID:CID_3032566
Chemical structure download


Dtxsid60911603
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.43
Log P RDKit 1.4
Topological polar surface area (Å2) RDKit 71.03
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
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 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Dtxsid60911603
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 0.58


Dtxsid60911603
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.92
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes