2.02012-07-30 14:55:41 -06002015-09-17 15:41:05 -0600ECMDB21386M2MDB001781CyanocobalaminB12 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. AlphamineAnacobinBerubigenBetalin 12 CrystallineBetaline-12BetolvexBevidoxBevidox concentrateBevidox concentric acidBiocobalamineByladoceCabadon mCobadoce forteCobalinCobaviteCopharvit 5000CovitCrystaminCrystamineCrystiminCrystwelCyano-B12Cyanobalamin concentrateCyanobalamin concentric acidCyanocob(III)alaminCyanocobalaminCyanocobalamin (JP15/USP)CyanocobalamineCyanocobalminCyanojectCycobeminCycolaminCykobeminCykobeminetCyominCyredinCytaconCytamenCytobionDepinarDicopacDimethylbenzimidazoylcobamideDistivitDocemineDocibinDocivitDodecabeeDodecaviteDodexDuodecibinEmbiolEmociclinaEritroneErycytolErythrotinEuhaemonExtrinsic factorFactor IIFerminFresminHemominHepagonHepavisHepcoviteHydrobexanHylugel plusLactobacillus lactis dorner factorMacrabinMegabionMegalovelMilbedoceMillevitNagravonNascobalNascobal (TN)NormocytinNovidroxinPernaemonPernaevitPernipuronPlecyaminPoyaminRebraminRedaminaRedisolRhodacrystRubesolRubraminRubripcaRubrocitolSytobexVibaltVibisoneVirubraVita-rubraVitamin B12Vitamin B12 PreparationVitarubinVitralC63H89CoN14O14P1356.37311355.575230332cyanocobalamincyanocobalamin68-19-9OC[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=C12InChI=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../s1SEKGMJVHSBBHRD-WZHZPDAFSA-MSolidCytoplasmlogp1.87logs-4.55solubility3.84e-02 g/lmelting_point>300 oCpka_strongest_acidic1.82pka_strongest_basic13.57iupaccyanocobalaminaverage_mass1356.3731mono_mass1355.575230332smilesOC[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=C12formulaC63H89CoN14O14PinchiInChI=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../s1inchikeySEKGMJVHSBBHRD-WZHZPDAFSA-Mpolar_surface_area487.61polarizability137.36acceptor_count15donor_count10physiological_charge0formal_charge0adenosylcobalamin salvage from cobinamideCobinamide 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 B12PW001884MetabolicSpecdb::EiMs2062Specdb::NmrOneD286035Specdb::NmrOneD286036Specdb::NmrOneD286037Specdb::NmrOneD286038Specdb::NmrOneD286039Specdb::NmrOneD286040Specdb::NmrOneD286041Specdb::NmrOneD286042Specdb::NmrOneD286043Specdb::NmrOneD286044Specdb::NmrOneD286045Specdb::NmrOneD286046Specdb::NmrOneD286047Specdb::NmrOneD286048Specdb::NmrOneD286049Specdb::NmrOneD286050Specdb::NmrOneD286051Specdb::NmrOneD286052Specdb::NmrOneD286053Specdb::NmrOneD286054Specdb::MsMs296539Specdb::MsMs296540Specdb::MsMs296541Specdb::MsMs337867Specdb::MsMs337868Specdb::MsMs337869Specdb::MsMs2694435Specdb::MsMs2694436Specdb::MsMs2694437Specdb::MsMs2987312Specdb::MsMs2987313Specdb::MsMs2987314HMDB006075462245C0282328911CPD-315Cyanocobalaminhttp://hmdb.ca/system/metabolites/msds/000/000/526/original/HMDB00607.pdf?1358893996Vitamin B12 import ATP-binding protein BtuDP06611BTUD_ECOLIbtuDhttp://ecmdb.ca/proteins/P06611.xmlVitamin B12 import system permease protein BtuCP06609BTUC_ECOLIbtuChttp://ecmdb.ca/proteins/P06609.xmlVitamin B12-binding proteinP37028BTUF_ECOLIbtuFhttp://ecmdb.ca/proteins/P37028.xmlVitamin B12 import ATP-binding protein BtuDP06611BTUD_ECOLIbtuDhttp://ecmdb.ca/proteins/P06611.xmlVitamin B12 import system permease protein BtuCB1XG18BTUC_ECODHbtuChttp://ecmdb.ca/proteins/B1XG18.xmlVitamin B12 import system permease protein BtuCC4ZYH3BTUC_ECOBWbtuChttp://ecmdb.ca/proteins/C4ZYH3.xmlVitamin B12 transporter BtuBP06129BTUB_ECOLIbtuBhttp://ecmdb.ca/proteins/P06129.xmlVitamin B12 import system permease protein BtuCP06609BTUC_ECOLIbtuChttp://ecmdb.ca/proteins/P06609.xmlVitamin B12-binding proteinP37028BTUF_ECOLIbtuFhttp://ecmdb.ca/proteins/P37028.xmlCyanocobalamin + Adenosine triphosphate + Water + Cyanocobalamin > Adenosine diphosphate + Phosphate + Hydrogen ion + Cyanocobalamin + ADPPW_RCT000170