(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-ide; cyanocobaltbis(ylium)

• ChemBase ID: 179534
• Molecular Formular: C63H88CoN14O14P
• Molecular Mass: 1355.365181
• Monoisotopic Mass: 1354.5674002
• SMILES: C1(C(/C/2=C(/C3=N/C(=C\C4=N/C(=C(\C5=NC(C1[N-]2)(C(C5CCC(=O)N)(CC(=O)N)C)C)/C)/C(C4CCC(=O)N)(CC(=O)N)C)/C(C3CCC(=O)N)(C)C)\C)(CCC(=O)NCC(OP(=O)(O[C@@H]1[C@@H](CO)O[C@H](n2c3c(cc(c(c3)C)C)nc2)[C@@H]1O)[O-])C)C)CC(=O)N.[Co+2]C#N
• Canonical SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(OC(CNC(=O)CCC1(C)/C/2=C(\C)/C3=N/C(=C\C4=N/C(=C(\C5=NC(C(C1CC(=O)N)[N-]2)(C)C(C)(CC(=O)N)C5CCC(=O)N)/C)/C(C4CCC(=O)N)(C)CC(=O)N)/C(C3CCC(=O)N)(C)C)C)[O-])O)n1cnc2c1cc(C)c(c2)C.N#C[Co+2]
• 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;;+2/p-2/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;;/m1../s1
• InChIKey: RMRCNWBMXRMIRW-ATSHILDLSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-ide; cyanocobaltbis(ylium)
• IUPAC Traditional name: (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-ide; cyanocobaltbis(ylium)
• Synonyms: 5,6-Dimethyl-1-(3-O-phosphono-α-D-ribofuranosyl)-1H-benzimidazole Monoester Cobinamide Cyanide Inner Salt; 5,6-Dimethylbenzimidazolyl Cyanocobamide; 5,6-Dimethylbenzimidazolyl-Co-cyanocobamide; Anacobin; Antipernicin; Apikobal; B-Twelve; B-Twelve Ora; Bedodeka; Bedoz; Behepan; Berubi; Berubigen; Dobetin; Docemine; Docibin; Poyamin; Rebramin; Redamina; Vitarubin; Vitral; Vitamin B12

Database IDs

• CAS Number: 68-19-9
• PubChem SID: 164235444
• PubChem CID: 71752967

CALCULATED PROPERTIES

• Polarizability: 129.30844 Å^3
• Polar Surface Area: 460.05 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false
• Acid pKa: 1.8412305
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -7.2647085
• LogD (pH = 7.4): -3.3802807
• Log P: -2.7134063
• Molar Refractivity: 330.719 cm^3

DETAILS

Toronto Research Chemicals - V676020

Prototype of the family of naturally occurring cobalt coordination compounds knows as corrinoids. Analogs of vitamin B12 which differ only in the β-ligand of the cobalt are termed cobalamins. Synthesized almost exclusively by bacteria. Dietary sources inc

REFERENCES

• Rickes, et al.: Science, 107, 396 (1948)
• Kirschbaum, J., et al.: Anal. Profiles Drug Subs., 10, 183 (1948)
• Grasbeck, R., et al.: Clin. Biochem., 17, 99 (1948)