1.0 2016-09-30 22:43:17 UTC 2020-06-04 19:55:18 UTC BMDB0001264 BMDB01264 Dehydroascorbic acid Dehydroascorbic acid, also known as dehydroascorbate or dhaa, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydroascorbic acid exists in all living organisms, ranging from bacteria to humans. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In cattle, dehydroascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway. Dehydroascorbate 1-Dehydroascorbate 1-Dehydroascorbic acid Dehydro-L-ascorbate Dehydro-L-ascorbic acid DHAA L-Dehydroascorbate L-Dehydroascorbic acid L-Threo-2,3-hexodiulosonic acid gamma-lactone L-Threo-hexo-2,3-diulosono-1,4-lactone Oxidized ascorbate Oxidized ascorbic acid Oxidized vitamin C Dehydroerythorbic acid C6H6O6 174.1082 174.016437924 (5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione (5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione 490-83-5 [H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1 SBJKKFFYIZUCET-DUZGATOHSA-N belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Organic compounds Organoheterocyclic compounds Lactones Gamma butyrolactones Gamma butyrolactones 1,2-diols Carboxylic acid esters Cyclic ketones Furanones Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Primary alcohols Secondary alcohols Tetrahydrofurans 1,2-diol 3-furanone Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic ketone Gamma butyrolactone Hydrocarbon derivative Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Primary alcohol Secondary alcohol Tetrahydrofuran Aliphatic heteromonocyclic compounds Solid logp -1.17 ALOGPS logs 0.04 ALOGPS logp -0.67 ChemAxon pka_strongest_acidic 1.56 ChemAxon pka_strongest_basic -3 ChemAxon iupac (5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione ChemAxon average_mass 174.1082 ChemAxon mono_mass 174.016437924 ChemAxon smiles [H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO ChemAxon formula C6H6O6 ChemAxon inchi InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1 ChemAxon inchikey SBJKKFFYIZUCET-DUZGATOHSA-N ChemAxon polar_surface_area 100.9 ChemAxon refractivity 33.55 ChemAxon polarizability 14.02 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Tyrosine Metabolism SMP0087235 Specdb::CMs 12979 Specdb::CMs 37999 Specdb::MsMs 1497 Specdb::MsMs 294517 Specdb::MsMs 294518 Specdb::MsMs 294519 Specdb::MsMs 335260 Specdb::MsMs 335261 Specdb::MsMs 335262 Specdb::NmrOneD 1674 Specdb::NmrTwoD 1615 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Erythrocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 2.240 +/- 0.172 uM Pasteurized whole milk Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74. 1880195 Milk 8.730 +/- 1.149 uM Raw milk Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74. 1880195 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 182283 C00425 210328 FDB021459 17242 34945 Dehydroascorbic acid 342 Utsumi, Isamu; Harada, Kiyoshi; Miura, Hiroshi. Dehydroascorbic acid. Jpn. Tokkyo Koho (1972), 2 pp. Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74. 1880195 BMDBP00655 Dopamine beta-hydroxylase P15101 DBH Enzyme BMDBP00665 Peptidyl-glycine alpha-amidating monooxygenase P10731 PAM Enzyme