IMPPAT Phytochemical information: 
Malabaric acid

Malabaric acid
Summary

SMILES: C/C/1=C\CC/C(=C\CC/C(=C/CC(CC1)C(=C)C)/C)/C(=O)O
InChI: InChI=1S/C20H30O2/c1-15(2)18-13-11-16(3)7-5-9-19(20(21)22)10-6-8-17(4)12-14-18/h7,10,12,18H,1,5-6,8-9,11,13-14H2,2-4H3,(H,21,22)/b16-7+,17-12+,19-10+
InChIKey: VEFNCYGNRHYTPX-UAIXMNOISA-N
DeepSMILES: C/C=C\CC/C=C\CC/C=C/CCCC\%14))C=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: 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:
malabaric acid, Malabaric acid
External chemical identifiers:
CID:CID_177567882
Chemical structure download


Malabaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.46
Log P RDKit 5.83
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 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 2
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


Malabaric 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 1
Ghose rule RDKit Failed
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 0.65


Malabaric 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