{[(2S,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[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: 156116
• 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}[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}[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: 162250254
• 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
• Safety Statements: 22-24/25
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (HPLC)
• Empirical Formula (Hill Notation): C72H100CoN18O17P

DETAILS

Sigma Aldrich - 27591

Other Notes
Review: The mechanism of adenosylcobalamine-dependent reactions1