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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:56 UTC
Update Date2019-07-23 06:08:41 UTC
HMDB IDHMDB0031403
Secondary Accession Numbers
  • HMDB31403
Metabolite Identification
Common NameCyclohexaneacetic acid
DescriptionCyclohexaneacetic acid, also known as cyclohexylethanoic acid or 2-cyclohexylacetate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Cyclohexaneacetic acid is a weakly acidic compound (based on its pKa). Cyclohexaneacetic acid is an acetic, caramel, and cheese. A monocarboxylic acid consisting of cyclohexane carrying a carboxymethyl substituent.
Structure
Data?1563862121
Synonyms
ValueSource
Cyclohexylethanoic acidChEBI
CyclohexylethanoateGenerator
CyclohexaneacetateGenerator
2-CyclohexylacetateHMDB
Cyclohexane-acetic acidHMDB
Cyclohexylacetic acidHMDB
FEMA 2347HMDB
Hexahydrophenylacetic acidHMDB
Cyclohexaneacetic acidChEBI
CyclohexylacetateGenerator
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Name2-cyclohexylacetic acid
Traditional Namecyclohexaneacetic acid
CAS Registry Number5292-21-7
SMILES
OC(=O)CC1CCCCC1
InChI Identifier
InChI=1S/C8H14O2/c9-8(10)6-7-4-2-1-3-5-7/h7H,1-6H2,(H,9,10)
InChI KeyLJOODBDWMQKMFB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.88 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.97 g/LALOGPS
logP2.53ALOGPS
logP2.08ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.42 m³·mol⁻¹ChemAxon
Polarizability15.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9000000000-b41e00ae96a1ce010432Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9000000000-b41e00ae96a1ce010432Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001m-9200000000-3d8ad65cdc383f430c9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gj-9400000000-7cdd05f72c97b91c269cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-b63c5ef41c7cf805c736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-1d638fea85a12d8a5e73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-2233ab05a2190a337741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-4900000000-f7f783e99f31ea43521fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-7900000000-204d44166f324eeec4ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-9c2931c97170ee18763eSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003477
KNApSAcK IDNot Available
Chemspider ID20080
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21363
PDB IDNot Available
ChEBI ID37277
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Iwaki H, Nakai E, Nakamura S, Hasegawa Y: Isolation and characterization of new cyclohexylacetic acid-degrading bacteria. Curr Microbiol. 2008 Aug;57(2):107-10. doi: 10.1007/s00284-008-9158-0. Epub 2008 Apr 8. [PubMed:18392890 ]
  2. Quesnel DM, Bhaskar IM, Gieg LM, Chua G: Naphthenic acid biodegradation by the unicellular alga Dunaliella tertiolecta. Chemosphere. 2011 Jul;84(4):504-11. doi: 10.1016/j.chemosphere.2011.03.012. Epub 2011 Apr 2. [PubMed:21459409 ]
  3. Valente MM, Bortolotto V, Cuccurazzu B, Ubezio F, Meneghini V, Francese MT, Canonico PL, Grilli M: alpha2delta ligands act as positive modulators of adult hippocampal neurogenesis and prevent depression-like behavior induced by chronic restraint stress. Mol Pharmacol. 2012 Aug;82(2):271-80. doi: 10.1124/mol.112.077636. Epub 2012 May 9. [PubMed:22572885 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .