2.0 2012-05-31 13:02:43 -0600 2015-06-03 15:53:38 -0600 ECMDB00965 M2MDB000212 Hypotaurine Hypotaurine is a product of enzyme cysteamine dioxygenase [EC 1.13.11.19] in taurine and hypotaurine metabolism pathway (KEGG). It may function as an antioxidant and a protective agent under physiological conditions (PMID 14992269). 2-Amino-Ethanesulfinate 2-Amino-Ethanesulfinic acid 2-Amino-Ethanesulphinate 2-Amino-Ethanesulphinic acid 2-Aminoethanesulfinate 2-Aminoethanesulfinic acid 2-Aminoethanesulphinate 2-Aminoethanesulphinic acid 2-Aminoethylsulfinate 2-Aminoethylsulfinic acid 2-Aminoethylsulphinate 2-Aminoethylsulphinic acid Cystaminesulfinate Cystaminesulfinic acid Cystaminesulphinate Cystaminesulphinic acid Hypotaurine C2H7NO2S 109.147 109.019749163 2-aminoethane-1-sulfinic acid hypotaurine 300-84-5 NCCS(O)=O InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5) VVIUBCNYACGLLV-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -1.19 ALOGPS logs -0.45 ALOGPS solubility 3.88e+01 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 1.68 ChemAxon pka_strongest_basic 9.64 ChemAxon iupac 2-aminoethane-1-sulfinic acid ChemAxon average_mass 109.147 ChemAxon mono_mass 109.019749163 ChemAxon smiles NCCS(O)=O ChemAxon formula C2H7NO2S ChemAxon inchi InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5) ChemAxon inchikey VVIUBCNYACGLLV-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 23.16 ChemAxon polarizability 10.16 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Taurine and hypotaurine metabolism ec00430 Specdb::CMs 686 Specdb::CMs 687 Specdb::CMs 688 Specdb::CMs 1280 Specdb::CMs 3386 Specdb::CMs 30036 Specdb::CMs 30192 Specdb::CMs 30573 Specdb::CMs 30762 Specdb::CMs 31272 Specdb::CMs 162575 Specdb::NmrOneD 1626 Specdb::NmrOneD 5144 Specdb::NmrOneD 5145 Specdb::NmrOneD 21082 Specdb::NmrOneD 21083 Specdb::NmrOneD 21084 Specdb::NmrOneD 21085 Specdb::NmrOneD 21086 Specdb::NmrOneD 21087 Specdb::NmrOneD 21088 Specdb::NmrOneD 21089 Specdb::NmrOneD 21090 Specdb::NmrOneD 21091 Specdb::NmrOneD 21092 Specdb::NmrOneD 21093 Specdb::NmrOneD 21094 Specdb::NmrOneD 21095 Specdb::NmrOneD 21096 Specdb::NmrOneD 21097 Specdb::NmrOneD 21098 Specdb::NmrOneD 21099 Specdb::NmrOneD 21100 Specdb::NmrOneD 21101 Specdb::MsMs 1369 Specdb::MsMs 1370 Specdb::MsMs 1371 Specdb::MsMs 4991 Specdb::MsMs 4992 Specdb::MsMs 4993 Specdb::MsMs 4994 Specdb::MsMs 4995 Specdb::MsMs 4996 Specdb::MsMs 4997 Specdb::MsMs 4998 Specdb::MsMs 4999 Specdb::MsMs 5000 Specdb::MsMs 5001 Specdb::MsMs 5002 Specdb::MsMs 5003 Specdb::MsMs 5004 Specdb::MsMs 5005 Specdb::MsMs 5006 Specdb::MsMs 5007 Specdb::MsMs 5008 Specdb::MsMs 5012 Specdb::MsMs 5013 Specdb::MsMs 182907 Specdb::MsMs 182908 Specdb::NmrTwoD 1567 HMDB00965 107812 96959 C00519 16668 HYPOTAURINE 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 Fontana, M., Pecci, L., Dupre, S., Cavallini, D. (2004). "Antioxidant properties of sulfinates: protective effect of hypotaurine on peroxynitrite-dependent damage." Neurochem Res 29:111-116. 14992269 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Dominy J, Eller S, Dawson R Jr: Building biosynthetic schools: reviewing compartmentation of CNS taurine synthesis. Neurochem Res. 2004 Jan;29(1):97-103. 14992267 Pitari G, Dupre S, Spirito A, Antonini G, Amicarelli F: Hypotaurine protection on cell damage by singlet oxygen. Adv Exp Med Biol. 2000;483:157-62. 11787593 Grafe F, Wohlrab W, Neubert RH, Brandsch M: Functional characterization of sodium- and chloride-dependent taurine transport in human keratinocytes. Eur J Pharm Biopharm. 2004 Mar;57(2):337-41. 15018993 Krieg RC, Uihlein D, Murthum T, Endlicher E, Hausmann F, Messmann H, Knuechel R: Improving the use of 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) for the gastrointestinal tract by esterification--an in vitro study. Cell Mol Biol (Noisy-le-grand). 2002 Dec;48(8):917-23. 12699251 Guerin P, Menezo Y: Hypotaurine and taurine in gamete and embryo environments: de novo synthesis via the cysteine sulfinic acid pathway in oviduct cells. Zygote. 1995 Nov;3(4):333-43. 8730898 Masuoka N, Yao K, Kinuta M, Ohta J, Wakimoto M, Ubuka T: High-performance liquid chromatographic determination of taurine and hypotaurine using 3,5-dinitrobenzoyl chloride as derivatizing reagent. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):31-5. 7858721 Guerin P, Guillaud J, Menezo Y: Hypotaurine in spermatozoa and genital secretions and its production by oviduct epithelial cells in vitro. Hum Reprod. 1995 Apr;10(4):866-72. 7650134 Holmes RP, Goodman HO, Shihabi ZK, Jarow JP: The taurine and hypotaurine content of human semen. J Androl. 1992 May-Jun;13(3):289-92. 1601750 Mahadevan MM, Trounson AO: Removal of the cumulus oophorus from the human oocyte for in vitro fertilization. Fertil Steril. 1985 Feb;43(2):263-7. 3967784 Owen, Terence C.; Wilbraham, A. C. Convenient preparation and characterization of hypotaurine. Journal of the Chemical Society (1965), (Jan.), 826-7. Glutamate decarboxylase alpha P69908 DCEA_ECOLI gadA http://ecmdb.ca/proteins/P69908.xml Glutamate decarboxylase beta P69910 DCEB_ECOLI gadB http://ecmdb.ca/proteins/P69910.xml 3-Sulfinoalanine <> Hypotaurine + Carbon dioxide R02466 3-Sulfinoalanine > Hypotaurine + Carbon dioxide + Hypotaurine PW_R002554