ChemFOnt: Showing chemical card for cis-4-Hydroxycyclohexylacetic acid (CFc000000345)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:42 UTC

Chemfont ID

CFc000000345

Molecule Identification

Common Name

cis-4-Hydroxycyclohexylacetic acid

Definition

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 (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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
cis-4-Hydroxycyclohexylacetate	Generator
4-Hydroxy-cyclohexylessigsaeure	HMDB
4-Hydroxycyclohexylacetate	HMDB
4-Hydroxycyclohexylacetic acid	HMDB
2-(4-Hydroxycyclohexyl)acetate	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular 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

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Urine (PMID: 26226126)
Feces (PMID: 20669995)

Cellular substructure

Cytoplasm (HMDB: HMDB0000451)
Extracellular (HMDB: HMDB0000451)

Source

Endogenous

Endogenous (HMDB: HMDB0000451)

Microbe

Microbe (HMDB: HMDB0000451)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Hawkinsinuria (HMDB: HMDB0000451)

Role

Industrial application

Pharmaceutical industry

Biomarker

Hawkinsinuria (MarkerDB: MDB00000164)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	27.1 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.69	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.09 m³·mol⁻¹	ChemAxon
Polarizability	16.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000451

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

METLIN ID

Not Available

PubChem Compound

12702257

PDB ID

Not Available

ChEBI ID

89344

Food Biomarker Ontology

Not Available

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

Showing chemical card for cis-4-Hydroxycyclohexylacetic acid (CFc000000345)

MOL for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

3D MOL for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

3D SDF for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

3D-SDF for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

PDB for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

3D PDB for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

SMILES for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

INCHI for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

Structure for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)

3D Structure for CFc000000345 (cis-4-Hydroxycyclohexylacetic acid)