(acetyloxy)[(6Z,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: 170237
• Molecular Formular: C64H91CoN13O16P
• Molecular Mass: 1388.391801
• Monoisotopic Mass: 1387.57763053
• SMILES: N1=C2C(C(/C/1=C(/C1=NC(C(C1CCC(=O)N)(CC(=O)N)C)(C1C(C(/C(=C(/C3=N/C(=C/2)/C(C3CCC(=O)N)(C)C)\C)/N1[Co+]OC(=O)C)(CCC(=O)NCC(OP(=O)([O-])O[C@H]1[C@H]([C@@H](n2c3c(cc(c(c3)C)C)nc2)O[C@@H]1CO)O)C)C)CC(=O)N)C)\C)(CC(=O)N)C)CCC(=O)N
• 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+]OC(=O)C)C)[O-])O)n1cnc2c1cc(C)c(c2)C
• InChI: InChI=1S/C62H90N13O14P.C2H4O2.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(3)4;/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);1H3,(H,3,4);/q;;+3/p-3/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;;/m1../s1
• InChIKey: KPFAAKYTRSSOQN-ATSHILDLSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)[(6Z,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: (acetyloxy)[(6Z,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: Cobinamide Acetate (Salt) Dihydrogen Phosphate (Ester) Inner Salt 3'-Ester with 5,6-Dimethyl-1-α-D-ribofuranosyl-1H-benzimidazole; Acetatocobalamin; Depo-gamma; Docelan; Fresmin S; Novidroxin; Twelvmin; Hydroxocobalamin Acetate

Database IDs

• CAS Number: 22465-48-1
• PubChem SID: 164226147
• PubChem CID: 71748889

CALCULATED PROPERTIES

• Acid pKa: 1.857509
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -7.804751
• LogD (pH = 7.4): -4.080143
• Log P: -3.653749
• Molar Refractivity: 342.2351 cm^3
• Polarizability: 137.25618 Å^3
• Polar Surface Area: 480.36 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Dark-Red Solid
• Melting Point: >300°C.

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H826800

Physiological analog of vitamin B12 where the CN group is replaced with OH. Exists in aqueous solution as an equilibrium mixture of the hydroxy isomer and the ionic aqua isomer (aquacobalamin). Precursor of the coenzymes methylcobalamin and cobamamide.

REFERENCES

• Kaczka, E.A., et al.: Science, 112, 354 (1950)
• Friedrich, W., et al.: Vitamins, 837 (1950)
• Forsyth, J.C., et al.: Clin. Toxicol., 31, 277 (1950)