IMPPAT Phytochemical information: 
Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-

Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-
Summary

SMILES: COC(=O)C([C@H]1C[C@@H]2N(CC1=CC)CCc1c2[nH]c2c1cccc2)C=O
InChI: InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,12,16-17,19,22H,8-11H2,1-2H3/t16-,17?,19-/m0/s1
InChIKey: AUOFTPXWUVYOOQ-VBIIVCKISA-N
DeepSMILES: COC=O)C[C@H]C[C@@H]NCC6=CC))))CCcc6[nH]cc5cccc6)))))))))))))))C=O
Scaffold Graph/Node/Bond level: C=C1CCC2c3[nH]c4ccccc4c3CCN2C1
Scaffold Graph/Node level: CC1CCC2C3NC4CCCCC4C3CCN2C1
Scaffold Graph level: CC1CCC2C(CCC3C4CCCCC4CC23)C1
Functional groups: COC(C)=O; CN(C)C; CC=C(C)C; c[nH]c; CC=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
geissoschizine
External chemical identifiers:
CID:CID_439666
Chemical structure download


Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 3.02
Topological polar surface area (Å2) RDKit 62.4
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 4
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


Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-
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 0.4


Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.87
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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