methyl[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16E,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-{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}-1,4,6,9,9,14,16,19-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: 172579
• Molecular Formular: C63H91CoN13O14P
• Molecular Mass: 1344.382301
• Monoisotopic Mass: 1343.58780129
• SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(OC(CNC(=O)CC[C@@]1(C)C2=N[C@H]([C@@H]1CC(=O)N)[C@]1(C)N([Co+]C)/C(=C(\C)/C3=N/C(=C\C4=N/C(=C\2/C)/[C@@H](CCC(=O)N)C4(C)C)/[C@H]([C@]3(C)CC(=O)N)CCC(=O)N)/[C@H]([C@]1(C)CC(=O)N)CCC(=O)N)C)[O-])O)n1cnc2c1cc(C)c(c2)C
• Canonical SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(OC(CNC(=O)CC[C@@]1(C)C2=N[C@H]([C@@H]1CC(=O)N)[C@]1(C)N([Co+]C)/C(=C(\C)/C3=N/C(=C\C4=N/C(=C\2/C)/[C@@H](CCC(=O)N)C4(C)C)/[C@H]([C@]3(C)CC(=O)N)CCC(=O)N)/[C@H]([C@]1(C)CC(=O)N)CCC(=O)N)C)[O-])O)n1cnc2c1cc(C)c(c2)C
• InChI: InChI=1S/C62H90N13O14P.CH3.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;;/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;/q;;+2/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
• InChIKey: JEWJRMKHSMTXPP-WYVZQNDMSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16E,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-{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}-1,4,6,9,9,14,16,19-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: methyl[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16E,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-{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}-1,4,6,9,9,14,16,19-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: Methyl-5,6-dimethylbenzimidazolylcobalamin; Methyl Vitamin B12; MeCbl; Algobaz; Hitocobamin-M; Methycobal; Methylcobaz; Mecobalamin

Database IDs

• CAS Number: 13422-55-4
• PubChem SID: 164228489
• PubChem CID: 71749922

CALCULATED PROPERTIES

• Acid pKa: 1.8547493
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -7.632207
• LogD (pH = 7.4): -3.7350152
• Log P: -3.119373
• Molar Refractivity: 336.6078 cm^3
• Polarizability: 134.56718 Å^3
• Polar Surface Area: 454.06 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Dark Red Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M202800

One of the biologically active forms of vitamin B12; differing only by the substitution of a methyl for the cyano group. Coenzyme required in the biosynthesis of methionine. Vitamin (hematopoietic).

REFERENCES

• Kisliuk, R.L., Biochem. J., 75, 467 (1960)
• Guest, J.R., et al.: Nature, 195, 340 (1960)
• Dolphin, D., et al.: Methods Enzymol., 18, 34 (1960)
• Beck, W.S., et al.: Am. J. Hematol., 34, 83 (1960)