hydroxy[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-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 hydrochloride

• ChemBase ID: 155930
• Molecular Formular: C62H90ClCoN13O15P
• Molecular Mass: 1382.816061
• Monoisotopic Mass: 1381.54374356
• SMILES: Cc1cc2c(cc1C)n(cn2)[C@@H]1[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(=N3)/C(=C\3/[C@@]([C@@H](C(=N3)/C=C\3/C([C@@H](C(=N3)/C(=C/1\N2[Co+]O)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.Cl
• Canonical SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(O[C@@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@H]2N(/C/1=C(/C)\C1=N/C(=C\C3=N/C(=C(\C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)/C)/[C@@]([C@@H]3CCC(=O)N)(C)CC(=O)N)/C([C@@H]1CCC(=O)N)(C)C)[Co+]O)C)[O-])O)n1cnc2c1cc(C)c(c2)C.Cl
• InChI: InChI=1S/C62H90N13O14P.ClH.Co.H2O/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);1H;;1H2/q;;+3;/p-3/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;;/m1.../s1
• InChIKey: KEHNCSYXYMMUCO-BXSGNKEGSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: hydroxy[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-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 hydrochloride
• IUPAC Traditional name: hydroxy[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-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 hydrochloride
• Synonyms: α-(5,6-Dimethylbenzimidazolyl)hydroxocobamide hydrochloride; Aquocobalamin chloride; Hydroxocobalamine hydrochloride; OH-Cbl HCl; Vitamin B12a; 维生素 B12a

Database IDs

• CAS Number: 78091-12-0
• EC Number: 261-200-3
• MDL Number: MFCD00167463
• PubChem SID: 24890104; 162250068
• PubChem CID: 46783759

CALCULATED PROPERTIES

• Acid pKa: 1.8410834
• H Acceptors: 18
• H Donor: 10
• LogD (pH = 5.5): -8.333373
• LogD (pH = 7.4): -4.5855017
• Log P: -4.143233
• Molar Refractivity: 333.0836 cm^3
• Polarizability: 133.40277 Å^3
• Polar Surface Area: 474.29 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: soluble10 mg/mL at 20 °C, clear, dark red

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC); ≥96% (UV)
• Loss on Drying: ≤12% loss on drying, 20 °C (HV)
• Empirical Formula (Hill Notation): C62H90ClCoN13O15P

DETAILS

Sigma Aldrich - 95200

Other Notes
Review1
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.