cyano[(1R,2R,3R,4R,8S,13S,14S,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: 156757
• Molecular Formular: C63H88CoN14O14P
• Molecular Mass: 1355.365181
• Monoisotopic Mass: 1354.5674002
• SMILES: Cc1cc2c(cc1C)n(cn2)C1[C@@H]([C@@H]([C@H](O1)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]1([C@H]([C@@H]2[C@]3([C@@]([C@@H](/C(=C(/C4=N/C(=C\C5=N/C(=C(\C1=N2)/C)/[C@H](C5(C)C)CCC(=O)N)/[C@H]([C@]4(C)CC(=O)N)CCC(=O)N)\C)/N3[Co+]C#N)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O
• 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,8S,13S,14S,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,8S,13S,14S,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: α-(5,6-Dimethylbenzimidazolyl)cyanocobamide; CN-Cbl; Cyanocob(III)alamin; Cyanocobalamin; Vitamin B12; Vitamin B12; Cyanocobalamin; Cyanocobalamin (B12); 氰钴胺; 维生素 B12; 维生素 B12; 氰钴胺; 腈钴胺（维生素 B12）

Database IDs

• CAS Number: 68-19-9
• EC Number: 200-680-0
• MDL Number: MFCD00151092
• Beilstein Number: 4122889
• PubChem SID: 24866963; 24871566; 24890103; 162250894
• PubChem CID: 16212801

CALCULATED PROPERTIES

• Acid pKa: 1.8546375
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -7.42668
• LogD (pH = 7.4): -3.669606
• Log P: -3.237631
• 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

• RTECS: GG3750000
• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0%; ≥98.0% (dried material)
• Grade: analytical standard; Ph Eur; SAJ special grade
• Packaging: ampule of 100 mg
• Suitability: passes test for foreign pigments
• Loss on Drying: ≤2% loss on drying
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Absorbance ratio: A361/278 nm 1.85 ±0.05
• Empirical Formula (Hill Notation): C63H88CoN14O14P

DETAILS

Sigma Aldrich - 95190

Other Notes
Review1

Sigma Aldrich - 47869

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 47869.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.