cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,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: 130828
• 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,6Z,8S,11Z,13S,14S,16Z,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,16Z,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; 氰钴胺; 维生素 B12; 氰钴胺; 维生素 B12

Database IDs

• CAS Number: 68-19-9
• EC Number: 200-680-0
• MDL Number: MFCD00151092
• Beilstein Number: 4122889
• PubChem SID: 24900763; 24900737; 162225106; 24892627; 24900725
• 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: ≥98%
• Suitability: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture

DETAILS

Sigma Aldrich - V6629

Application
Required for growth, genetic stability and survival of cells in vitro. Functions to support one-carbon metabolism. Present in many classical and serum-free formulations.

Sigma Aldrich - V2876

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Vitamin B12 (cobalamin) refers to a group of chemically-related cobalt containing molecules involved in cell processes such as DNA synthesis, fatty acid synthesis, energy production and regulation. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms. Bacteria-derived hydroxocobalamin (OHCbl) and CNCbl are converted in humans to useful coenzyme forms to support metabolic processes such as mitochondrial methylmalonylcoenzyme A mutase conversion of methylmalonic acid (MMA) to succinate to link lipid and carbohydrate metabolism, and activation of methionine synthase, the rate limiting step in the synthesis of methionine.

Sigma Aldrich - V2006

Biochem/physiol Actions
Cobalamin may be important to form organometallic bonds in nature and as a precursor of methylcobalamin. Methycobalamin is important for methionine biosynthesis and 5’-deoxyadenosyl cobalamin supports class II ribonucleotide reductase reactions.

Sigma Aldrich - C3607

Application
维持体外细胞的生长、遗传稳定性和存活所必需。具有支持一碳代谢的作用。存在于许多传统无血清配方中。