cyano[(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-{[(2R)-2-{[(2R,3S,4R)-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: 295341
• Molecular Formular: C63H88CoN14O14P
• Molecular Mass: 1355.365181
• Monoisotopic Mass: 1354.5674002
• SMILES: OC[C@H]1OC([C@@H]([C@@H]1OP(=O)(O[C@@H](CNC(=O)CC[C@@]1(C)C2=N[C@H]([C@@H]1CC(=O)N)[C@]1(C)N([Co+]C#N)/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]1OC([C@@H]([C@@H]1OP(=O)(O[C@@H](CNC(=O)CC[C@@]1(C)C2=N[C@H]([C@@H]1CC(=O)N)[C@]1(C)N([Co+]C#N)/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.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-QJRSUKKJSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: cyano[(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-{[(2R)-2-{[(2R,3S,4R)-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: cyano[(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-{[(2R)-2-{[(2R,3S,4R)-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: Cyanocobalamine; Vitamin B12; 维生素B12

Database IDs

• CAS Number: 68-19-9
• EC Number: 200-680-0
• MDL Number: MFCD00151092
• Beilstein Number: 4122889
• Merck Index: 1410014
• PubChem SID: 180680872
• PubChem CID: 73995027

CALCULATED PROPERTIES

• Acid pKa: 1.8166317
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -7.426672
• LogD (pH = 7.4): -3.6696057
• Log P: -3.2376313
• Molar Refractivity: 337.4833 cm^3
• Polarizability: 134.45374 Å^3
• Polar Surface Area: 477.85 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Warning: Hygroscopic
• RTECS: GG3750000
• TSCA Listed: 是

Product Information

• Purity: 98+% (dry wt basis)

REFERENCES

• For review of biosynthesis, see: Angew. Chem. Int. Ed., 32, 1223 (1993).
• For monographs, see: B₁₂(2 vols), D. Dolphon, Ed., Wiley-Interscience, N.Y. (1982); B₁₂ and B₁₂-Proteins, B. Kraeutler, T Golding, Eds., Wiley-VCH, Weinheim (1998).
• For a review, see: Vitamins, W. Friedrich, Ed., de Gruyter, Berlin (1988), pp 837-928.