| Common Name |
cis-4-Hydroxycyclohexylacetic acid
| Description |
Cis-4-hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27), an inborn error of metabolism. (PMIDs 701419, 719903). 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 regliated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones. (OMIM: 609695 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
4-Hydroxy-cyclohexylessigsaeureHMDB
4-HydroxycyclohexylacetateHMDB
cis-4-HydroxycyclohexylacetateHMDB
4-Hydroxycyclohexylacetic acidMeSH
| Chemical Formlia |
C8H14O3
| Average Molecliar Weight |
158.195
| Monoisotopic Molecliar Weight |
158.094294314
| IUPAC Name |
2-(4-hydroxycyclohexyl)acetic acid
| Traditional Name |
4-hydroxycyclohexylacetate
| CAS Registry Number |
68592-22-3
| 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 Key |
ALTAAUJNHYWOGS-UHFFFAOYSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility27.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.09 m3·mol-1ChemAxon
Polarizability16.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Feces
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
FecesDetected but not Quantified Adlit (>18 years old)Both
Normal
24029555
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
20669995
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdlit (>18 years old)BothHawkinsinuria
MetaGene
details
UrineDetected and Quantified40.00 (10.00-70.00) umol/mmol creatinineChildren (1-13 years old)BothHawkinsinuria
MetaGene
details
| Associated Disorders and Diseases |
| Disease References |
| Hawkinsinuria |
- MetaGene [Link]
| Associated OMIM IDs |
140350 (Hawkinsinuria)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022054
| KNApSAcK ID |
Not Available
| Chemspider ID |
13628091
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00451
| Metagene Link |
HMDB00451
| METLIN ID |
Not Available
| PubChem Compound |
12702257
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Nicainoprol
References |
| Synthesis Reference |
Ungnade, 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 |
Not Available |
PMID: 3691669