IMPPAT Phytochemical information: 
2-Acetoxymalabaric acid

2-Acetoxymalabaric acid
Summary

SMILES: CC(=O)OC1/C=C(/C)\CC/C=C(\CC/C=C(\CCC1C(=C)C)/C)/C(=O)O
InChI: InChI=1S/C22H32O4/c1-15(2)20-13-12-16(3)8-6-10-19(22(24)25)11-7-9-17(4)14-21(20)26-18(5)23/h8,11,14,20-21H,1,6-7,9-10,12-13H2,2-5H3,(H,24,25)/b16-8-,17-14-,19-11+
InChIKey: UEZWBWGIEOHSAA-RHFHHHDOSA-N
DeepSMILES: CC=O)OC/C=C/C)\CC/C=C\CC/C=C\CCC%14C=C)C)))))/C)))))/C=O)O
Scaffold Graph/Node/Bond level: C1=CCCC=CCCCCC=CCC1
Scaffold Graph/Node level: C1CCCCCCCCCCCCC1
Scaffold Graph level: C1CCCCCCCCCCCCC1
Functional groups: COC(C)=O; C/C=C(/C)C; C/C=C(/C(=O)O)C; C=C(C)C
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: Cembrane diterpenoids
Synonymous chemical names:
2-acetoxymalabaric acid
External chemical identifiers:
CID:CID_101593160
Chemical structure download


2-Acetoxymalabaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.49
Log P RDKit 5.37
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


2-Acetoxymalabaric acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.54


2-Acetoxymalabaric 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 -6.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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