2.0 2012-05-31 09:55:53 -0600 2015-09-17 15:41:01 -0600 ECMDB00044 M2MDB000013 Ascorbic acid Ascorbic acid is the biologically active form of vitamin C. Ascorbic acid is an electron donor for enzymes involved in the biosynthesis of carnitine and tyrosine metabolism. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. (+)-ascorbate (+)-ascorbic acid (+)-Sodium L-ascorbate (+)-Sodium L-ascorbic acid 3-Keto-L-gulofuranolactone 3-Oxo-L-gulofuranolactone Adenex Allercorb Antiscorbic vitamin Antiscorbutic vitamin Arco-cee Ascoltin Ascor-B.I.D. Ascorb Ascorbajen Ascorbate Ascorbic acid Ascorbicab Ascorbicap Ascorbicin Ascorbin Ascorbutina Ascorin Ascorteal Ascorvit C-Level C-Long C-Quin C-Span C-Vimin Cantan Cantaxin Catavin C Ce lent Ce-mi-lin Ce-vi-sol Cebicure Cebid Cebion Cebione Cecon Cee-caps TD Cee-vite Cegiolan Ceglion Ceklin Celaskon Celin Cell C Cemagyl Cemill Cenetone Cenolate Cenolic acid Cereon Cergona Cescorbat Cetamid Cetane Cetane-caps TC Cetane-caps TD Cetebe Cetemican Cevalin Cevatine Cevex Cevi-bid Cevimin Cevital Cevitamate Cevitamic acid Cevitamin Cevitan Cevitex Cewin Chewcee Ciamin Cipca Citriscorb Citrovit Colascor Concemin Davitamon C Dora-C-500 Duoscorb Ferrous ascorbate Ferrous ascorbic acid g-Lactone L-threo-hex-2-enonate g-Lactone L-threo-hex-2-enonic acid Gamma-Lactone L-threo-Hex-2-enonate Gamma-Lactone L-threo-Hex-2-enonic acid Hexuronate Hexuronic acid HiCee Hybrin Ido-C Juvamine Kangbingfeng Kyselina askorbova L(+)-Ascorbate L(+)-Ascorbic acid L-(+)-Ascorbate L-(+)-Ascorbic acid L-3-Ketothreohexuronate lactone L-3-Ketothreohexuronic acid lactone L-Ascorbate L-Ascorbate (vitamin C) L-Ascorbic acid L-Ascorbic acid (vitamin C) L-Lyxoascorbate L-Lyxoascorbic acid L-Threo-ascorbate L-Threo-ascorbic acid L-Xyloascorbate L-Xyloascorbic acid Laroscorbine Lemascorb Liqui-cee Meri-c Natrascorb Natrascorb injectable Planavit C Proscorbin Redoxon Ribena Ronotec 100 Rontex 100 Roscorbic Rovimix C Scorbacid Scorbu C Scorbu-C Secorbate Secorbic acid Sodascorbate Sodascorbic acid Suncoat VC 40 Testascorbic VASC Vicelat Vicin Vicomin C Viforcit Viscorin Viscorin 100M Vitace Vitacee Vitacimin Vitacin Vitamin C Vitamisin Vitascorbol Xitix γ-Lactone L-threo-hex-2-enonate γ-Lactone L-threo-hex-2-enonic acid C6H8O6 176.1241 176.032087988 (2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2,3-dihydrofuran-3-one (2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2H-furan-3-one 50-81-7 [H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1 CIWBSHSKHKDKBQ-JLAZNSOCSA-N Solid Extra-organism Periplasm logp -1.87 ALOGPS logs 0.16 ALOGPS solubility 2.57e+02 g/l ALOGPS melting_point 191 oC logp -1.3 ChemAxon pka_strongest_acidic 0.72 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2,3-dihydrofuran-3-one ChemAxon average_mass 176.1241 ChemAxon mono_mass 176.032087988 ChemAxon smiles [H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO ChemAxon formula C6H8O6 ChemAxon inchi InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1 ChemAxon inchikey CIWBSHSKHKDKBQ-JLAZNSOCSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 46.26 ChemAxon polarizability 14.98 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Ascorbate and aldarate metabolism ec00053 Phosphotransferase system (PTS) ec02060 Ascorbate metabolism E. coli is able to utilize L-ascorbate (vitamin C) as the sole source of carbon under anaerobic and aerobic conditions. Ascorbic acid in the cytoplasm is processed through a spontaneous reaction with a hydrogen ion and hydrogen peroxide, producing water, dehydroascorbic acid and ascorbic acid. Dehydroascorbic acid reacts with water spontaneously producing an isomer, dehydroascorbate (bicyclic form). The compound then loses a hydrogen ion resulting in a 2,3-Diketo-L-gulonate. This compound is then reduced through a NADH dependent 2,3 diketo-L-gulonate reductase, releasing a NAD and 3-Dehydro-L-gulonate.This compound is phosphorylated through an ATP mediated L-xylulose/3-keto-L-gulonate kinase resulting in an ADP, hydrogen ion and a 3-Keto-L-gulonate 6 phosphate. L-ascorbate can also be imported and converted to L-ascorbate-6-phosphate by the L-ascorbate PTS transporter. L-ascorbate-6-phosphate reacts with a probable L-ascorbate-6-phosphate lactonase ulaG, resulting in a 3-keto-L-gulonate 6-phosphate. The compound 3-keto-L-gulonate 6-phosphate can be processed aerobically or anaerobically. Aerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by a 3-keto-L-gulonate-6-phosphate decarboxylase ulaD, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by L-ribulose-5-phosphate 3-epimerase ulaE, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase ulaF resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Anaerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by 3-keto-L-gulonate 6-phosphate decarboxylase sgbH, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by predicted L-xylulose 5-phosphate 3-epimerase, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Expression of the ula regulon is regulated by the L-ascorbate 6-phosphate-binding repressor UlaR and by cAMP-CRP. Under aerobic conditions, metabolism of L-ascorbate is hindered by the special reactivity and toxicity of this compound in the presence of oxygen. PW000793 Metabolic L-ascorbate degradation II (bacterial, aerobic) PWY-6961 Specdb::NmrOneD 1050 Specdb::MsMs 75 Specdb::MsMs 76 Specdb::MsMs 77 Specdb::NmrTwoD 941 Specdb::NmrTwoD 1108 HMDB00044 644104 559144 C00072 29073 ASCORBATE Ascorbic acid Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 http://hmdb.ca/system/metabolites/msds/000/000/031/original/HMDB00044.pdf?1358893460 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Putative phosphotransferase enzyme IIA component yadI P36881 YADI_ECOLI yadI http://ecmdb.ca/proteins/P36881.xml Ascorbate-specific phosphotransferase enzyme IIA component P69820 ULAC_ECOLI ulaC http://ecmdb.ca/proteins/P69820.xml Ascorbate-specific phosphotransferase enzyme IIB component P69822 ULAB_ECOLI ulaB http://ecmdb.ca/proteins/P69822.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 Protein N(pi)-phospho-L-histidine + Ascorbic acid <> Protein histidine + L-Ascorbate 6-phosphate R07671 an oxidized electron acceptor + Ascorbic acid + Hydrogen ion > a reduced electron acceptor + monodehydroascorbate RXN-10981 Ascorbic acid + Hydrogen peroxide > monodehydroascorbate + Water RXN-3521 monodehydroascorbate + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate RXN-3523 Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 Ascorbic acid + Hydrogen peroxide + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate + Water RXN-12440 Ascorbic acid + Hydrogen peroxide + Hydrogen ion > Ascorbic acid + L-dehydro-ascorbate + Water RXN-12440 Ascorbic acid + HPr - phosphorylated + Ascorbic acid > L-ascorbate 6-phosphate + HPr + L-Ascorbate 6-phosphate PW_RCT000136