2.0 2012-07-30 14:55:41 -0600 2015-09-17 15:41:05 -0600 ECMDB21386 M2MDB001781 Cyanocobalamin B12 is the most chemically complex of all the vitamins. B12's structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Vitamin B12 cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of B12 are bacteria and archaea. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. Alphamine Anacobin Berubigen Betalin 12 Crystalline Betaline-12 Betolvex Bevidox Bevidox concentrate Bevidox concentric acid Biocobalamine Byladoce Cabadon m Cobadoce forte Cobalin Cobavite Copharvit 5000 Covit Crystamin Crystamine Crystimin Crystwel Cyano-B12 Cyanobalamin concentrate Cyanobalamin concentric acid Cyanocob(III)alamin Cyanocobalamin Cyanocobalamin (JP15/USP) Cyanocobalamine Cyanocobalmin Cyanoject Cycobemin Cycolamin Cykobemin Cykobeminet Cyomin Cyredin Cytacon Cytamen Cytobion Depinar Dicopac Dimethylbenzimidazoylcobamide Distivit Docemine Docibin Docivit Dodecabee Dodecavite Dodex Duodecibin Embiol Emociclina Eritrone Erycytol Erythrotin Euhaemon Extrinsic factor Factor II Fermin Fresmin Hemomin Hepagon Hepavis Hepcovite Hydrobexan Hylugel plus Lactobacillus lactis dorner factor Macrabin Megabion Megalovel Milbedoce Millevit Nagravon Nascobal Nascobal (TN) Normocytin Novidroxin Pernaemon Pernaevit Pernipuron Plecyamin Poyamin Rebramin Redamina Redisol Rhodacryst Rubesol Rubramin Rubripca Rubrocitol Sytobex Vibalt Vibisone Virubra Vita-rubra Vitamin B12 Vitamin B12 Preparation Vitarubin Vitral C63H89CoN14O14P 1356.3731 1355.575230332 cyanocobalamin cyanocobalamin 68-19-9 OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@]([H])(C)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co]C#N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)N1C=NC2=CC(C)=C(C)C=C12 InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1 SEKGMJVHSBBHRD-WZHZPDAFSA-M Solid Cytoplasm logp 1.87 ALOGPS logs -4.55 ALOGPS solubility 3.84e-02 g/l ALOGPS melting_point >300 oC pka_strongest_acidic 1.82 ChemAxon pka_strongest_basic 13.57 ChemAxon iupac cyanocobalamin ChemAxon average_mass 1356.3731 ChemAxon mono_mass 1355.575230332 ChemAxon smiles OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@]([H])(C)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co]C#N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)N1C=NC2=CC(C)=C(C)C=C12 ChemAxon formula C63H89CoN14O14P ChemAxon inchi InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1 ChemAxon inchikey SEKGMJVHSBBHRD-WZHZPDAFSA-M ChemAxon polar_surface_area 487.61 ChemAxon polarizability 137.36 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon adenosylcobalamin salvage from cobinamide Cobinamide is incorporated from the extracellular space through a transport system into the cytosol. Once inside the cytosol, cobinamide interacts with ATP through a cobinamide adenosyl transferase resulting in the release of a triphosphate and an adenosylcobinamide. The latter compound is then phosphorylated through an ATP-dependent cobinamide kinase resulting in the release of ADP, a hydrogen ion and adenosyl-cobinamide phosphate. This last compound then interacts with GTP and a hydrogen ion through a cobinamide-P guanylyltransferase resulting in the release of a pyrophosphate and an adenosylcobinamide-GDP. A dimethylbenzimidazole interacts with a nicotinate D-ribonucleotide through a nicotinate-nucleotide dimethylbenzumidazole phosphoribosyltransferase resulting in the release of a nicotinate, a hydrogen ion and an alpha-ribazole 5' phosphate. The adenosylcobinamide-GDP and the alpha-ribazole 5' phosphate interact together through a cobalamin 5' phosphate synthase resulting in the release of a hydrogen ion, a GMP and Adenosylcobalamin 5'-phosphate. The latter compound then interacts with a water molecule through an adenosylcbalamin 5' phosphate phosphatase resulting in the release of a phosphate and a coenzyme B12. Likewise a cobalamin molecule can interact with ATP through a cobalamin adenosyltransferase resulting in the release of a triphosphate and a coenzyme B12 PW001884 Metabolic Specdb::EiMs 2062 Specdb::NmrOneD 286035 Specdb::NmrOneD 286036 Specdb::NmrOneD 286037 Specdb::NmrOneD 286038 Specdb::NmrOneD 286039 Specdb::NmrOneD 286040 Specdb::NmrOneD 286041 Specdb::NmrOneD 286042 Specdb::NmrOneD 286043 Specdb::NmrOneD 286044 Specdb::NmrOneD 286045 Specdb::NmrOneD 286046 Specdb::NmrOneD 286047 Specdb::NmrOneD 286048 Specdb::NmrOneD 286049 Specdb::NmrOneD 286050 Specdb::NmrOneD 286051 Specdb::NmrOneD 286052 Specdb::NmrOneD 286053 Specdb::NmrOneD 286054 Specdb::MsMs 296539 Specdb::MsMs 296540 Specdb::MsMs 296541 Specdb::MsMs 337867 Specdb::MsMs 337868 Specdb::MsMs 337869 Specdb::MsMs 2694435 Specdb::MsMs 2694436 Specdb::MsMs 2694437 Specdb::MsMs 2987312 Specdb::MsMs 2987313 Specdb::MsMs 2987314 HMDB00607 5462245 C02823 28911 CPD-315 Cyanocobalamin http://hmdb.ca/system/metabolites/msds/000/000/526/original/HMDB00607.pdf?1358893996 Vitamin B12 import ATP-binding protein BtuD P06611 BTUD_ECOLI btuD http://ecmdb.ca/proteins/P06611.xml Vitamin B12 import system permease protein BtuC P06609 BTUC_ECOLI btuC http://ecmdb.ca/proteins/P06609.xml Vitamin B12-binding protein P37028 BTUF_ECOLI btuF http://ecmdb.ca/proteins/P37028.xml Vitamin B12 import ATP-binding protein BtuD P06611 BTUD_ECOLI btuD http://ecmdb.ca/proteins/P06611.xml Vitamin B12 import system permease protein BtuC B1XG18 BTUC_ECODH btuC http://ecmdb.ca/proteins/B1XG18.xml Vitamin B12 import system permease protein BtuC C4ZYH3 BTUC_ECOBW btuC http://ecmdb.ca/proteins/C4ZYH3.xml Vitamin B12 transporter BtuB P06129 BTUB_ECOLI btuB http://ecmdb.ca/proteins/P06129.xml Vitamin B12 import system permease protein BtuC P06609 BTUC_ECOLI btuC http://ecmdb.ca/proteins/P06609.xml Vitamin B12-binding protein P37028 BTUF_ECOLI btuF http://ecmdb.ca/proteins/P37028.xml Cyanocobalamin + Adenosine triphosphate + Water + Cyanocobalamin > Adenosine diphosphate + Phosphate + Hydrogen ion + Cyanocobalamin + ADP PW_RCT000170