Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0001988
Secondary Accession Numbers
  • HMDB01988
Metabolite Identification
Common Name4-Hydroxycyclohexylcarboxylic acid
Description4-Hydroxycyclohexylcarboxylic acid belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. 4-Hydroxycyclohexylcarboxylic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-hydroxycyclohexylcarboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Hydroxycyclohexylcarboxylic acid.
Structure
Data?1582752222
Synonyms
ValueSource
4-HydroxycyclohexylcarboxylateGenerator
4-Hydroxycyclohexane-1-carboxylic acidHMDB
4-Hydroxycyclohexanecarboxylic acidHMDB, MeSH
4-HCHCMeSH, HMDB
4-Hydroxycyclohexane-1-carboxylateGenerator, HMDB
Chemical FormulaC7H12O3
Average Molecular Weight144.1684
Monoisotopic Molecular Weight144.07864425
IUPAC Name4-hydroxycyclohexane-1-carboxylic acid
Traditional Name4-hydroxycyclohexane-1-carboxylic acid
CAS Registry Number17419-81-7
SMILES
OC1CCC(CC1)C(O)=O
InChI Identifier
InChI=1S/C7H12O3/c8-6-3-1-5(2-4-6)7(9)10/h5-6,8H,1-4H2,(H,9,10)
InChI KeyHCFRWBBJISAZNK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Cyclic alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP0.56ALOGPS
logP0.5ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.52 m³·mol⁻¹ChemAxon
Polarizability14.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.18831661259
DarkChem[M-H]-128.68331661259
DeepCCS[M+H]+129.30730932474
DeepCCS[M-H]-126.53130932474
DeepCCS[M-2H]-163.04330932474
DeepCCS[M+Na]+137.89130932474
AllCCS[M+H]+133.232859911
AllCCS[M+H-H2O]+128.732859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.532859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-132.432859911
AllCCS[M+HCOO]-134.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxycyclohexylcarboxylic acidOC1CCC(CC1)C(O)=O2648.0Standard polar33892256
4-Hydroxycyclohexylcarboxylic acidOC1CCC(CC1)C(O)=O1303.8Standard non polar33892256
4-Hydroxycyclohexylcarboxylic acidOC1CCC(CC1)C(O)=O1371.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxycyclohexylcarboxylic acid,1TMS,isomer #1C[Si](C)(C)OC1CCC(C(=O)O)CC11466.5Semi standard non polar33892256
4-Hydroxycyclohexylcarboxylic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C1CCC(O)CC11420.3Semi standard non polar33892256
4-Hydroxycyclohexylcarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C)CC11504.2Semi standard non polar33892256
4-Hydroxycyclohexylcarboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCC(C(=O)O)CC11715.1Semi standard non polar33892256
4-Hydroxycyclohexylcarboxylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O)CC11663.4Semi standard non polar33892256
4-Hydroxycyclohexylcarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CC11956.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid GC-EI-TOF (Non-derivatized)splash10-00ea-0930000000-847fab622854d89692402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid GC-EI-TOF (Non-derivatized)splash10-00ea-0930000000-847fab622854d89692402018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004v-9100000000-4c1f052d143e49157a802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-5930000000-0d79b67d3319b73f908f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-057i-3900000000-abc6ac16f21e5ce068442012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-88770293822bd2e9b1d92012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0059-9000000000-35f3ef9952979b17e3962012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 40V, Negative-QTOFsplash10-0005-9000000000-1b2cea72343cecc8e91b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 10V, Negative-QTOFsplash10-0006-0900000000-96b59c40cd0d646bd69f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 20V, Negative-QTOFsplash10-0007-8900000000-057e4d949aac31b312602021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 10V, Positive-QTOFsplash10-004j-2900000000-8fe3526038b3ae3e8c9d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 20V, Positive-QTOFsplash10-057j-7900000000-8e6b4bce93588dedbed02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 40V, Positive-QTOFsplash10-05o0-9000000000-1ed081d3979985a45ba02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 10V, Negative-QTOFsplash10-0006-3900000000-59651bf351fcc5fcf4bb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 20V, Negative-QTOFsplash10-0035-9700000000-6e8062fddb5dc431fcd12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 40V, Negative-QTOFsplash10-000t-9100000000-1800082b5d54d2e7dc912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 10V, Negative-QTOFsplash10-0006-2900000000-9c4062159f99a6e082372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 20V, Negative-QTOFsplash10-001m-9200000000-d66d5f669e271d14dede2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 40V, Negative-QTOFsplash10-0006-9000000000-b48b8d0bf36e587fd68e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 10V, Positive-QTOFsplash10-000t-9500000000-795337373081b3c6fe8f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 20V, Positive-QTOFsplash10-053s-9200000000-ff4f103a5daa54c211142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxycyclohexylcarboxylic acid 40V, Positive-QTOFsplash10-0pbc-9000000000-ac84b42ef25ecdf001792021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified5.9 (0.1-112.4) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified4.4 (1.5-15.4) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified6.1 (1.1-28.1) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022785
KNApSAcK IDNot Available
Chemspider ID133210
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151138
PDB IDNot Available
ChEBI ID16817
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceInoue, Goro; Kato, Toshio; Oshima, Noboru. 4-Hydroxycyclohexanecarboxylic acid and its related compounds. Jpn. Tokkyo Koho (1968), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Sewell AC, Bohles HJ: 4-Hydroxycyclohexanecarboxylic acid: a rare compound in urinary organic acid analysis. Clin Chem. 1991 Jul;37(7):1301-2. [PubMed:1855310 ]