{[(2S,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(6Z,11Z,16Z)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-{2-[(2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl)carbamoyl]ethyl}-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.12,5.17,10.112,15]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium

• ChemBase ID: 132492
• Molecular Formular: C72H100CoN18O17P
• Molecular Mass: 1579.581761
• Monoisotopic Mass: 1578.65834046
• SMILES: Cc1cc2c(cc1C)n(cn2)[C@@H]1[C@@H]([C@@H]([C@H](O1)CO)OP(=O)([O-])OC(C)CNC(=O)CCC1(C(C2C3(C(C(C(=N3)/C(=C\3/C(C(C(=N3)/C=C\3/C(C(C(=N3)/C(=C/1\N2[Co+]C[C@@H]1[C@H]([C@H]([C@H](O1)n1cnc2c1ncnc2N)O)O)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O
• Canonical SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(OC(CNC(=O)CCC1(C)C(CC(=O)N)C2N(/C/1=C(/C)\C1=N/C(=C\C3=N/C(=C(\C4=NC2(C)C(C)(CC(=O)N)C4CCC(=O)N)/C)/C(C3CCC(=O)N)(C)CC(=O)N)/C(C1CCC(=O)N)(C)C)[Co+]C[C@H]1O[C@@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)C)[O-])O)n1cnc2c1cc(C)c(c2)C
• InChI: InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;4-,6-,7-,10+;/m11./s1
• InChIKey: ZIHHMGTYZOSFRC-PMDPKNCCSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(6Z,11Z,16Z)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-{2-[(2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl)carbamoyl]ethyl}-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^2,^5.1^7,^1^0.1^1^2,^1^5]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
• IUPAC Traditional name: {[(2S,3S,4R,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(6Z,11Z,16Z)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-{2-[(2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl)carbamoyl]ethyl}-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^2,^5.1^7,^1^0.1^1^2,^1^5]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
• Synonyms: 5′-Deoxyadenosylcobalamine; Adenosyl cobalamine; Cobamamide; DMBC coenzyme; Coenzyme B12

Database IDs

• CAS Number: 13870-90-1
• EC Number: 237-627-6
• MDL Number: MFCD00135609
• Beilstein Number: 4122932
• PubChem SID: 162226769; 24892282
• PubChem CID: 71308568

CALCULATED PROPERTIES

• Acid pKa: 1.816338
• H Acceptors: 24
• H Donor: 12
• LogD (pH = 5.5): -9.819938
• LogD (pH = 7.4): -5.9816422
• Log P: -5.556217
• Molar Refractivity: 391.316 cm^3
• Polarizability: 155.87791 Å^3
• Polar Surface Area: 573.37 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GG3800000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0%

DETAILS

Sigma Aldrich - C0884

Biochem/physiol Actions
Vitamin B12 (cobalamin) refers to a group of chemically-related cobalt containing molecules involved in cell processes such as DNA synthesis, fatty acid synthesis, energy production and regulation. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms. Bacteria-derived hydroxocobalamin (OHCbl) and CNCbl are converted in humans to useful coenzyme forms to support metabolic processes such as mitochondrial methylmalonylcoenzyme A mutase conversion of methylmalonic acid (MMA) to succinate to link lipid and carbohydrate metabolism, and activation of methionine synthase, the rate limiting step in the synthesis of methionine.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C0884.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.