IMPPAT Phytochemical information: 
(2|A,6|A,9|A)-2-hydroxy-6,18-epoxypimara-7,15-dien-18-one

(2|A,6|A,9|A)-2-hydroxy-6,18-epoxypimara-7,15-dien-18-one
Summary

SMILES: C=C[C@]1(C)CC[C@@H]2C(=C[C@@H]3[C@@H]4[C@]2(C)C[C@H](O)C[C@@]4(C(=O)O3)C)C1
InChI: InChI=1S/C20H28O3/c1-5-18(2)7-6-14-12(9-18)8-15-16-19(14,3)10-13(21)11-20(16,4)17(22)23-15/h5,8,13-16,21H,1,6-7,9-11H2,2-4H3/t13-,14+,15+,16+,18+,19+,20-/m0/s1
InChIKey: VSXVHWPQGHHXGS-GYNABYOXSA-N
DeepSMILES: C=C[C@]C)CC[C@@H]C=C[C@@H][C@@H][C@]6C)C[C@H]O)C[C@@]6C=O)O9))C)))))))))C6
Scaffold Graph/Node/Bond level: O=C1OC2C=C3CCCCC3C3CCCC1C23
Scaffold Graph/Node level: OC1OC2CC3CCCCC3C3CCCC1C23
Scaffold Graph level: CC1CC2CC3CCCCC3C3CCCC1C23
Functional groups: C=CC; CC(=CC)C; CO; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Norpimarane and Norisopimarane diterpenoids|Pimarane and Isopimarane diterpenoids
Synonymous chemical names:
momilactone c
External chemical identifiers:
CID:CID_188452; ZINC:ZINC000006067331
Chemical structure download


(2|A,6|A,9|A)-2-hydroxy-6,18-epoxypimara-7,15-dien-18-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.44
Log P RDKit 3.63
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


(2|A,6|A,9|A)-2-hydroxy-6,18-epoxypimara-7,15-dien-18-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.593414


(2|A,6|A,9|A)-2-hydroxy-6,18-epoxypimara-7,15-dien-18-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.65
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No