IMPPAT Phytochemical information: 
Geranic acid

Geranic acid
Summary

SMILES: CC(=CCC/C(=C/C(=O)O)/C)C
InChI: InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+
InChIKey: ZHYZQXUYZJNEHD-VQHVLOKHSA-N
DeepSMILES: CC=CCC/C=C/C=O)O)))/C)))))C
Functional groups: CC=C(C)C; C/C(C)=C/C(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Monoterpenoids
NP Classifier Biosynthetic pathway: Fatty acids|Terpenoids
NP Classifier Superclass: Fatty Acids and Conjugates|Monoterpenoids
NP Classifier Class: Acyclic monoterpenoids|Branched fatty acids|Unsaturated fatty acids
Synonymous chemical names:
gerainic-acid, geranoic acid, geranic-acid, Geranic acid, geranoic-acid, geranic acid
External chemical identifiers:
CID:CID_5275520; ChEMBL:CHEMBL170190; ChEBI:CHEBI:67264; ZINC:ZINC000001758085; FDASRS:10797G3M5Y; SureChEMBL:SCHEMBL358253; MolPort-001-769-750
Chemical structure download


Geranic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.24
Log P RDKit 2.76
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 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
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 0


Geranic acid
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 0.517363


Geranic 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 -5.13
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No