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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:25 UTC
Update Date2019-07-23 06:08:32 UTC
HMDB IDHMDB0031342
Secondary Accession Numbers
  • HMDB31342
Metabolite Identification
Common NameCyclohexanecarboxylic acid
DescriptionCyclohexanecarboxylic acid, also known as hexahydrobenzoic acid or carboxycyclohexane, 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. Cyclohexanecarboxylic acid is a weakly acidic compound (based on its pKa). Cyclohexanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Cyclohexanecarboxylic acid is an acidic, cheese, and fruity tasting compound. Outside of the human body,. A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group.
Structure
Data?1563862112
Synonyms
ValueSource
CarboxycyclohexaneChEBI
CyclohexancarbonsaeureChEBI
Cyclohexane-1-carboxylateChEBI
Cyclohexanoic acidChEBI
Cyclohexylcarboxylic acidChEBI
Cyclohexylformic acidChEBI
Cyclohexylmethanoic acidChEBI
Hexahydrobenzoic acidChEBI
Cyclohexane-1-carboxylic acidGenerator
CyclohexanoateGenerator
CyclohexylcarboxylateGenerator
CyclohexylformateGenerator
CyclohexylmethanoateGenerator
HexahydrobenzoateGenerator
CyclohexanecarboxylateGenerator
7549-42-0 (Calcium salt)HMDB
FEMA 3531HMDB
Hexahydro-benzoic acidHMDB
Naphthenic acidHMDB
Naphthenoic acidHMDB
Cyclohexanecarboxylic acid, calcium saltHMDB
Cyclohexanecarboxylic acid, cobalt saltHMDB
Cyclohexanecarboxylic acid, potassium saltHMDB
Cyclohexanecarboxylic acid, sodium saltHMDB
Cyclohexanecarboxylic acid, sodium salt, 11C-labeledHMDB
Cyclohexanecarboxylic acid, lead saltHMDB
Chemical FormulaC7H12O2
Average Molecular Weight128.169
Monoisotopic Molecular Weight128.083729628
IUPAC Namecyclohexanecarboxylic acid
Traditional Namecyclohexanecarboxylic acid
CAS Registry Number98-89-5
SMILES
OC(=O)C1CCCCC1
InChI Identifier
InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
InChI KeyNZNMSOFKMUBTKW-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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point31 - 32 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.6 mg/mL at 25 °CNot Available
LogP1.96Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.01 g/LALOGPS
logP1.88ALOGPS
logP1.89ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.85 m³·mol⁻¹ChemAxon
Polarizability14.03 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)splash10-03e9-9700000000-afedc669010cea1fff7aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9700000000-afedc669010cea1fff7aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-9100000000-7b2d7325908346fef2d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008i-9300000000-6340158dcee214fd3ad4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-69422c2f22908125487eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-1900000000-2b1c359177d442da9138Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056s-9500000000-8b79211c98aa33e6b31aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a73dd06af262b4a9ef25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-0018f47571feaf232ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3900000000-5f7af485316f5734f31cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9400000000-4891c30e0de9b93142c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-4e84d360f5dcc7c27e10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-e6c3bee1d7b7769e57d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9500000000-9de2d40e8ed9e23f88feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-e176edd2be2d6a23fcc9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified29.102 +/- 57.424 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified205.198 +/- 493.879 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003406
KNApSAcK IDC00000334
Chemspider ID7135
KEGG Compound IDC09822
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclohexanecarboxylic_acid
METLIN IDNot Available
PubChem Compound7413
PDB IDNot Available
ChEBI ID36096
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mo R, Sun Q, Xue J, Li N, Li W, Zhang C, Ping Q: Multistage pH-responsive liposomes for mitochondrial-targeted anticancer drug delivery. Adv Mater. 2012 Jul 17;24(27):3659-65. doi: 10.1002/adma.201201498. Epub 2012 Jun 8. [PubMed:22678851 ]
  2. BALTES BJ, ELLIOTT WH, DOISY EA Jr, DOISY EA: Biochemical studies of hexahydrobenzoic acid and hexahydrophenylalanine. J Biol Chem. 1952 Feb;194(2):627-34. [PubMed:14927655 ]
  3. MITOMA C, POSNER HS, LEONARD F: Aromatization of hexahydrobenzoic acid by mamalian liver mitochondria. Biochim Biophys Acta. 1958 Jan;27(1):156-60. [PubMed:13510261 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .