IMPPAT Phytochemical information: 
15-Hydroxyabieta-7,13-dien-18-oic acid

15-Hydroxyabieta-7,13-dien-18-oic acid
Summary

SMILES: OC(=O)[C@]1(C)CCC[C@]2([C@H]1CC=C1[C@@H]2CCC(=C1)C(O)(C)C)C
InChI: InChI=1S/C20H30O3/c1-18(2,23)14-7-8-15-13(12-14)6-9-16-19(15,3)10-5-11-20(16,4)17(21)22/h6,12,15-16,23H,5,7-11H2,1-4H3,(H,21,22)/t15-,16+,19+,20+/m0/s1
InChIKey: BYQLYGRDILHOFF-LNKGRISISA-N
DeepSMILES: OC=O)[C@]C)CCC[C@][C@H]6CC=C[C@@H]6CCC=C6)CO)C)C))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2=CCC3CCCCC3C2CC1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: CC(=O)O; CC=C(C)C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Abietane diterpenoids
Synonymous chemical names:
15-hydroxyabietic acid
External chemical identifiers:
CID:CID_643004; ZINC:ZINC000032302901
Chemical structure download


15-Hydroxyabieta-7,13-dien-18-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 318.46
Log P RDKit 4.32
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
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 4
Stereochemical complexity RDKit 0.2
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 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3


15-Hydroxyabieta-7,13-dien-18-oic acid
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.8


15-Hydroxyabieta-7,13-dien-18-oic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.86
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes