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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:11 UTC
HMDB IDHMDB0000451
Secondary Accession Numbers
  • HMDB00451
Metabolite Identification
Common Namecis-4-Hydroxycyclohexylacetic acid
Descriptioncis-4-Hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (or HPPD) (EC 1.13.11.27), an inborn error of metabolism (PMIDs 701419, 719903) also called hawkinsinuria. 4-Hydroxyphenylpyruvate dioxygenase participates in the tyrosine catabolic pathway by catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate (Hager et al., 1957). The mechanism of action of 4-hydroxyphenylpyruvate dioxygenase involves a decarboxylation step and an oxidation step, followed by a rearrangement step to form homogentisic acid (Tomoeda et al., 2000). Awata et al. (1994) determined that the HPD gene contains 14 exons. Analysis of the 5-prime flanking sequence of the gene suggested that expression of the gene is regulated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones (OMIM: 609695 ). cis-4-Hydroxycyclohexylacetic acid has also been found to be a microbial metabolite (PMID: 20615997 ).
Structure
Data?1563860651
Synonyms
ValueSource
cis-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexylessigsaeureHMDB
4-HydroxycyclohexylacetateHMDB
4-Hydroxycyclohexylacetic acidHMDB
2-(4-Hydroxycyclohexyl)acetateHMDB
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Name2-(4-hydroxycyclohexyl)acetic acid
Traditional Name4-hydroxycyclohexylacetate
CAS Registry Number68592-22-3
SMILES
OC1CCC(CC(O)=O)CC1
InChI Identifier
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)
InChI KeyALTAAUJNHYWOGS-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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility27.1 g/LALOGPS
logP0.93ALOGPS
logP0.69ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.09 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9400000000-abc03a0f8f17c7d423a2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-6950000000-e954349d2bba3a1f7bdaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-2900000000-cdb682550fd7986a0a1cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-9800000000-a24c028ad8e3ba7b5049JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00o4-9000000000-3cefeadb5ca0dbfbb8e7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-228641a4fa5e65521acfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-3900000000-2731aa44b1316101793fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9300000000-382927881c2cd816ee47JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Urine
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 Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0 - 2.2 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified230-1100 umol/mmol creatinineChildren (1 - 13 years old)MaleHawkinsinuria details
UrineDetected and Quantified5.6 - 57.3 umol/mmol creatinineNewborn (0-30 days old)BothHawkinsinuria 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 ]
Hawkinsinuria
  1. Lehnert W, Stogmann W, Engelke U, Wevers RA, van den Berg GB: Long-term follow up of a new case of hawkinsinuria. Eur J Pediatr. 1999 Jul;158(7):578-82. [PubMed:10412819 ]
  2. Thodi G, Schulpis KH, Dotsikas Y, Pavlides C, Molou E, Chatzidaki M, Triantafylli O, Loukas YL: Hawkinsinuria in two unrelated Greek newborns: identification of a novel variant, biochemical findings and treatment. J Pediatr Endocrinol Metab. 2016 Jan;29(1):15-20. doi: 10.1515/jpem-2015-0132. [PubMed:26226126 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022054
KNApSAcK IDNot Available
Chemspider ID13628091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12702257
PDB IDNot Available
ChEBI ID89344
References
Synthesis ReferenceUngnade, Herbert E.; Morriss, Francis V. Hydrogenation of phenolic acids. Journal of the American Chemical Society (1948), 70 1898-9. CODEN: JACSAT ISSN:0002-7863. CAN 42:29753 AN 1948:29753
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]