1.0 2011-09-21 00:23:39 UTC 2018-05-29 01:52:56 UTC FDB023037 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida species (PMID:20423563). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. [HMDB] (3-Hydroxyphenyl)hydracrylate (3-Hydroxyphenyl)hydracrylic acid 3-(3-hydroxyphenyl)-3-hydroxypropanoate 3-(3-hydroxyphenyl)-3-hydroxypropanoic acid 3-(3-Hydroxyphenyl)-3-hydroxypropionate 3-(3-Hydroxyphenyl)-3-hydroxypropionic acid 3-(3-Hydroxyphenyl)hydracrylate 3-(3-Hydroxyphenyl)hydracrylic acid 3-(m-Hydroxyphenyl)hydracrylate 3-(m-Hydroxyphenyl)hydracrylic acid 3-Hydroxy-3-(3-hydroxyphenyl)propionic acid 3-Hydroxyphenyl-hydracrylic acid 3'-Hydroxyphenylhydracrylic acid b-(m-Hydroxyphenyl)hydracrylate b-(m-Hydroxyphenyl)hydracrylic acid beta-(m-Hydroxyphenyl)hydracrylate beta-(m-Hydroxyphenyl)hydracrylic acid HPHPA C9H10O4 182.1733 182.057908808 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid mhpha 3247-75-4 OC(CC(O)=O)C1=CC(O)=CC=C1 InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13) KHTAGVZHYUZYMF-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Phenylpropanoic acids Organic compounds Phenylpropanoids and polyketides Phenylpropanoic acids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aromatic alcohols Benzene and substituted derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3-phenylpropanoic-acid Alcohol Aromatic alcohol Aromatic homomonocyclic compound Benzenoid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Secondary alcohol dihydroxy monocarboxylic acid phenols Solid logp 0.68 ALOGPS logs -1.46 ALOGPS solubility 6.31e+00 g/l ALOGPS logp 0.68 ChemAxon pka_strongest_acidic 3.94 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles OC(CC(O)=O)C1=CC(O)=CC=C1 ChemAxon formula C9H10O4 ChemAxon inchi InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13) ChemAxon inchikey KHTAGVZHYUZYMF-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 45.31 ChemAxon polarizability 17.31 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1832 Specdb::CMs 5710 Specdb::CMs 38451 Specdb::CMs 135625 Specdb::CMs 143359 Specdb::MsIr 1809 Specdb::MsIr 1810 Specdb::MsMs 86574 Specdb::MsMs 86575 Specdb::MsMs 86576 Specdb::MsMs 148899 Specdb::MsMs 148900 Specdb::MsMs 148901 Specdb::MsMs 2400920 Specdb::MsMs 2400921 Specdb::MsMs 2400922 Specdb::MsMs 2537885 Specdb::MsMs 2537886 Specdb::MsMs 2537887 Specdb::NmrOneD 1896 Specdb::NmrOneD 122718 Specdb::NmrOneD 122719 Specdb::NmrOneD 122720 Specdb::NmrOneD 122721 Specdb::NmrOneD 122722 Specdb::NmrOneD 122723 Specdb::NmrOneD 122724 Specdb::NmrOneD 122725 Specdb::NmrOneD 122726 Specdb::NmrOneD 122727 Specdb::NmrOneD 122728 Specdb::NmrOneD 122729 Specdb::NmrOneD 122730 Specdb::NmrOneD 122731 Specdb::NmrOneD 122732 Specdb::NmrOneD 122733 Specdb::NmrOneD 122734 Specdb::NmrOneD 122735 Specdb::NmrOneD 122736 Specdb::NmrOneD 122737 Specdb::NmrOneD 166335 Specdb::NmrOneD 166661 Specdb::NmrOneD 166663 HMDB02643 #<Reference:0x000055ce32352860> #<Reference:0x000055ce323526a8> 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