1.0 2011-09-21 00:07:42 UTC 2015-07-21 06:56:57 UTC FDB022054 cis-4-Hydroxycyclohexylacetic acid 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 regulated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones. (OMIM: 609695) [HMDB] 4-Hydroxy-cyclohexylessigsaeure 4-Hydroxycyclohexylacetate cis-4-Hydroxycyclohexylacetate cis-4-Hydroxycyclohexylacetic acid C8H14O3 158.195 158.094294314 2-(4-hydroxycyclohexyl)acetic acid 4-hydroxycyclohexylacetate 68592-22-3 OC1CCC(CC(O)=O)CC1 InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11) ALTAAUJNHYWOGS-UHFFFAOYSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclohexanol Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Solid logp 0.93 ALOGPS logs -0.77 ALOGPS solubility 2.71e+01 g/l ALOGPS logp 0.69 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac 2-(4-hydroxycyclohexyl)acetic acid ChemAxon average_mass 158.195 ChemAxon mono_mass 158.094294314 ChemAxon smiles OC1CCC(CC(O)=O)CC1 ChemAxon formula C8H14O3 ChemAxon inchi InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11) ChemAxon inchikey ALTAAUJNHYWOGS-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 40.09 ChemAxon polarizability 16.85 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21991 Specdb::CMs 37545 Specdb::CMs 150313 Specdb::CMs 1062950 Specdb::CMs 1062952 Specdb::CMs 1062954 Specdb::CMs 1062956 Specdb::CMs 1062958 Specdb::NmrOneD 6802 Specdb::NmrOneD 6803 Specdb::NmrOneD 6804 Specdb::NmrOneD 6805 Specdb::NmrOneD 6806 Specdb::NmrOneD 6807 Specdb::NmrOneD 6808 Specdb::NmrOneD 6809 Specdb::NmrOneD 6810 Specdb::NmrOneD 6811 Specdb::NmrOneD 6812 Specdb::NmrOneD 6813 Specdb::NmrOneD 6814 Specdb::NmrOneD 6815 Specdb::NmrOneD 6816 Specdb::NmrOneD 6817 Specdb::NmrOneD 6818 Specdb::NmrOneD 6819 Specdb::NmrOneD 6820 Specdb::NmrOneD 6821 Specdb::MsMs 69999 Specdb::MsMs 70000 Specdb::MsMs 70001 Specdb::MsMs 128421 Specdb::MsMs 128422 Specdb::MsMs 128423 Specdb::MsMs 2725121 Specdb::MsMs 2725122 Specdb::MsMs 2725123 Specdb::MsMs 2957592 Specdb::MsMs 2957593 Specdb::MsMs 2957594 HMDB00451 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823