2.0 2012-05-31 10:24:24 -0600 2015-10-02 02:25:47 -0600 ECMDB00235 M2MDB000097 Thiamine Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. It is a metabolite in E. coli, a substrate for enzyme thiamin kinase (gene name: thiK) which catalyzes the chemical reaction thiamin + ATP -> thiamin phosphate + ADP + H+ (EcoCyc compound: THIAMINE). Aneurin Antiberiberi factor Apate drops Apic acid drops Beatine Bedome Begiolan Benerva Bequin Berin Betalin S Betaxin Bethiazine Beuion Bevitex Bevitine Bewon Biamine Bithiamin Biuno Bivatin Bivita Cernevit-12 Clotiamina Eskapen Eskaphen Hybee Lixa-b Lixa-beta Lixa-β Metabolin Slowten THD Thiadoxine Thiamin Thiaminal Thiamine Thiaminium Thiamol Thiavit Tiamidon Tiaminal Trophite Vetalin S VIB Vinothiam Vitamin B1 Vitamin B<SUB>1</SUB> Vitaneuron C12H17N4OS 265.355 265.112306876 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium thiamine 59-43-8 CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1 JZRWCGZRTZMZEH-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -2.11 ALOGPS logs -4.29 ALOGPS solubility 1.53e-02 g/l ALOGPS melting_point 248 oC logp -3.1 ChemAxon pka_strongest_acidic 15.5 ChemAxon pka_strongest_basic 5.54 ChemAxon iupac 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium ChemAxon average_mass 265.355 ChemAxon mono_mass 265.112306876 ChemAxon smiles CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N ChemAxon formula C12H17N4OS ChemAxon inchi InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1 ChemAxon inchikey JZRWCGZRTZMZEH-UHFFFAOYSA-N ChemAxon polar_surface_area 75.91 ChemAxon refractivity 73.4 ChemAxon polarizability 28.14 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Thiamine metabolism ec00730 ABC transporters ec02010 Sulfur relay system ec04122 Metabolic pathways eco01100 Specdb::CMs 3244 Specdb::CMs 37377 Specdb::CMs 168506 Specdb::CMs 1055128 Specdb::CMs 1055130 Specdb::CMs 1055131 Specdb::NmrOneD 1211 Specdb::NmrOneD 1255 Specdb::NmrOneD 4799 Specdb::NmrOneD 4800 Specdb::NmrOneD 143130 Specdb::NmrOneD 143131 Specdb::NmrOneD 143132 Specdb::NmrOneD 143133 Specdb::NmrOneD 143134 Specdb::NmrOneD 143135 Specdb::NmrOneD 143136 Specdb::NmrOneD 143137 Specdb::NmrOneD 143138 Specdb::NmrOneD 143139 Specdb::NmrOneD 143140 Specdb::NmrOneD 143141 Specdb::NmrOneD 143142 Specdb::NmrOneD 143143 Specdb::NmrOneD 143144 Specdb::NmrOneD 143145 Specdb::NmrOneD 143146 Specdb::NmrOneD 143147 Specdb::NmrOneD 143148 Specdb::NmrOneD 143149 Specdb::NmrOneD 166493 Specdb::MsMs 394 Specdb::MsMs 395 Specdb::MsMs 396 Specdb::MsMs 3699 Specdb::MsMs 3700 Specdb::MsMs 3701 Specdb::MsMs 3702 Specdb::MsMs 3703 Specdb::MsMs 3704 Specdb::MsMs 3705 Specdb::MsMs 3706 Specdb::MsMs 3707 Specdb::MsMs 3708 Specdb::MsMs 3709 Specdb::MsMs 3710 Specdb::MsMs 3711 Specdb::MsMs 3712 Specdb::MsMs 3713 Specdb::MsMs 179757 Specdb::MsMs 179758 Specdb::MsMs 179759 Specdb::MsMs 182091 Specdb::MsMs 182092 Specdb::MsMs 182093 Specdb::MsMs 438547 Specdb::NmrTwoD 1004 Specdb::NmrTwoD 1228 HMDB00235 1130 1098 C00378 18385 THIAMINE VIB Thiamine Keseler, I. 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Journal of Organic Chemistry (1990), 55(2), 467-70. http://hmdb.ca/system/metabolites/msds/000/000/170/original/HMDB00235.pdf?1358463414 Thiamine kinase P75948 THIK_ECOLI thiK http://ecmdb.ca/proteins/P75948.xml Thiamine transport system permease protein thiP P31549 THIP_ECOLI thiP http://ecmdb.ca/proteins/P31549.xml Thiamine import ATP-binding protein ThiQ P31548 THIQ_ECOLI thiQ http://ecmdb.ca/proteins/P31548.xml Thiamine-binding periplasmic protein P31550 THIB_ECOLI thiB http://ecmdb.ca/proteins/P31550.xml Thiamine transport system permease protein thiP P31549 THIP_ECOLI thiP http://ecmdb.ca/proteins/P31549.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 Thiamine import ATP-binding protein ThiQ P31548 THIQ_ECOLI thiQ http://ecmdb.ca/proteins/P31548.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 Thiamine-binding periplasmic protein P31550 THIB_ECOLI thiB http://ecmdb.ca/proteins/P31550.xml Adenosine triphosphate + Water + Thiamine > ADP + Hydrogen ion + Phosphate + Thiamine ABC-32-RXN Adenosine triphosphate + Water + Thiamine > ADP + Hydrogen ion + Phosphate + Thiamine ABC-32-RXN Adenosine triphosphate + Thiamine <> ADP + Hydrogen ion + Thiamine monophosphate R02134 THIKIN-RXN Adenosine triphosphate + Thiamine <> ADP + Thiamine monophosphate R02134 Adenosine triphosphate + Thiamine + Water > ADP + Phosphate + Thiamine + Hydrogen ion ABC-32-RXN Adenosine triphosphate + Thiamine + Water > ADP + Phosphate + Thiamine + Hydrogen ion ABC-32-RXN Thiamine + Adenosine triphosphate > Hydrogen ion + Thiamine monophosphate + ADP THIKIN-RXN Adenosine triphosphate + Thiamine > ADP + Thiamine monophosphate