IMPPAT Phytochemical information: 
Abietic Acid

Abietic Acid
Summary

SMILES: CC(C1=CC2=CC[C@@H]3[C@]([C@H]2CC1)(C)CCC[C@@]3(C)C(=O)O)C
InChI: InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
InChIKey: RSWGJHLUYNHPMX-ONCXSQPRSA-N
DeepSMILES: CCC=CC=CC[C@@H][C@][C@H]6CC%10)))C)CCC[C@@]6C)C=O)O)))))))))))))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=C(C)C=C(C)C; CC(=O)O
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:
Abietic Acid
External chemical identifiers:
CID:CID_10569; ChEMBL:CHEMBL71893; ChEBI:CHEBI:28987; ZINC:ZINC000002267806; FDASRS:V3DHX33184; SureChEMBL:SCHEMBL28888; Molport-002-507-350
Chemical structure download


Abietic Acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.46
Log P RDKit 5.21
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 2
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


Abietic Acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.760294


Abietic Acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -4.75
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No