IMPPAT Phytochemical information: 
(12S,13R)-9-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.01,15.02,10.04,8]nonadeca-2(10),3,8,15,17-pentaen-19-one
(12S,13R)-9-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.01,15.02,10.04,8]nonadeca-2(10),3,8,15,17-pentaen-19-one
Summary

SMILES: COC1=C(OC)C(=O)C23C(=C1)C[C@H]([C@]3(C)Cc1c2c(OC)c2c(c1O)OCO2)C
InChI: InChI=1S/C22H24O7/c1-10-6-11-7-13(25-3)16(26-4)20(24)22(11)14-12(8-21(10,22)2)15(23)18-19(17(14)27-5)29-9-28-18/h7,10,23H,6,8-9H2,1-5H3/t10-,21+,22?/m1/s1
InChIKey: NHHDUOLOCUZQIE-FEELHUIYSA-N
DeepSMILES: COC=COC))C=O)CC=C6)C[C@H][C@]5C)Ccc8cOC))ccc6O))OCO5))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC=C2CCC3Cc4cc5c(cc4C123)OCO5
Scaffold Graph/Node level: OC1CCCC2CCC3CC4CC5OCOC5CC4C123
Scaffold Graph level: CC1CCCC2CCC3CC4CC5CCCC5CC4C123
Functional groups: COC1=C(OC)C(=O)CC(=C1)C; cOC; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzocyclooctadienes lignans
Synonymous chemical names:
heteroclitin g
External chemical identifiers:
CID:CID_101630513
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(12S,13R)-9-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.01,15.02,10.04,8]nonadeca-2(10),3,8,15,17-pentaen-19-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 400.43
Log P RDKit 2.98
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
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 11
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
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 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(12S,13R)-9-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.01,15.02,10.04,8]nonadeca-2(10),3,8,15,17-pentaen-19-one
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.84
(12S,13R)-9-hydroxy-3,17,18-trimethoxy-12,13-dimethyl-5,7-dioxapentacyclo[10.7.0.01,15.02,10.04,8]nonadeca-2(10),3,8,15,17-pentaen-19-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.67
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes