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Record Information
Version4.0
Creation Date2006-05-22 14:17:45 UTC
Update Date2017-09-27 08:24:14 UTC
HMDB IDHMDB0002274
Secondary Accession Numbers
  • HMDB02274
Metabolite Identification
Common NameMethylcobalamin
DescriptionThe name vitamin B12 is used in two different ways. In a broad sense it refers to a group of cobalt-containing compounds known as cobalamins - cyanocobalamin (an artifact formed as a result of the use of cyanide in the purification procedures), hydroxocobalamin and the two coenzyme forms of B12, methylcobalamin (MeB12) and 5-deoxyadenosylcobalamin (adenosylcobalamin - AdoB12). In a more specific way, the term B12 is used to refer to only one of these forms, cyanocobalamin, which is the principal B12 form used for foods and in nutritional supplements. B12 cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of B12 are bacteria and archaea. The total synthesis of B12 was reported in 1973 by Robert Burns Woodward, and remains one of the classic feats of total synthesis. Cyanocobalamin is a vitamin commonly known as vitamin B12 (or B12 for short).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC63H92CoN13O14P
Average Molecular Weight1345.3902
Monoisotopic Molecular Weight1344.595631423
IUPAC Nameλ⁴-cobalt(4+) ion 1-(3-hydroxy-4-{[hydroxy({[1-({1-hydroxy-3-[8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-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-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl)-5,6-dimethyl-3H-1λ⁵,3-benzodiazol-1-ylium methane
Traditional Nameλ⁴-cobalt(4+) ion 1-[3-hydroxy-4-({hydroxy[1-({1-hydroxy-3-[8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-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-4-yl]propylidene}amino)propan-2-yl]oxyphosphoryl}oxy)-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1λ⁵,3-benzodiazol-1-ylium methane
CAS Registry Number13422-55-4
SMILES
C.[Co+4].CC(CN=C(O)CCC1(C)C(CC(O)=N)C2N=C1C(C)=C1N=C(C=C3N=C(C(C)=C4NC2(C)C(C)(CC(O)=N)C4CCC([O-])=N)C(C)(CC(O)=N)C3CCC([O-])=N)C(C)(C)C1CCC([O-])=N)OP(O)(=O)OC1C(CO)OC(C1O)[N+]1=CNC2=C1C=C(C)C(C)=C2
InChI Identifier
InChI=1S/C62H90N13O14P.CH4.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);1H4;/q;;+4/p-2
InChI KeyDAWIHDLSSOERNY-UHFFFAOYSA-L
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassCorrinoids
Direct ParentCobalamin derivatives
Alternative Parents
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • 1-ribofuranosylbenzimidazole
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Benzenoid
  • Fatty acyl
  • Tetrahydrofuran
  • Pyrroline
  • Pyrrolidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketimine
  • Carboximidic acid derivative
  • Carbene-type 1,3-dipolar compound
  • Carboximidic acid
  • Organic transition metal salt
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic salt
  • Organic oxygen compound
  • Imine
  • Organic cobalt salt
  • Organic oxide
  • Hydrocarbon derivative
  • Saturated hydrocarbon
  • Hydrocarbon
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological Location:

  Cell and elements:

    Cell:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.1ChemAxon
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area479.79 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity430.84 m³·mol⁻¹ChemAxon
Polarizability132.62 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0009000000-270ebe7bf52ebc393bc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-0009000000-837bcde718484550d5d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-0009000000-9cdd3a31b906175760adView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Fibroblasts
  • Myelin
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.000220 +/- 8.410e-05 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.000221 +/- 8.983e-05 uMAdult (>18 years old)Not Specifiedfibromyalgia details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022939
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06453
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylcobalamin
METLIN ID6587
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28115
References
Synthesis ReferenceTollinger, Martin; Derer, Tomas; Konrat, Robert; Kraeutler, Bernhard. An efficient method for the preparation of methylcobalamin, nature's organometallic methyl transfer catalyst. Journal of Molecular Catalysis A: Chemical (1997), 116(1-2), 147-155.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Koyama K, Usami T, Takeuchi O, Morozumi K, Kimura G: Efficacy of methylcobalamin on lowering total homocysteine plasma concentrations in haemodialysis patients receiving high-dose folic acid supplementation. Nephrol Dial Transplant. 2002 May;17(5):916-22. [PubMed:11981084 ]
  2. Roze E, Gervais D, Demeret S, Ogier de Baulny H, Zittoun J, Benoist JF, Said G, Pierrot-Deseilligny C, Bolgert F: Neuropsychiatric disturbances in presumed late-onset cobalamin C disease. Arch Neurol. 2003 Oct;60(10):1457-62. [PubMed:14568819 ]
  3. Frisbie SM, Chance MR: Human cobalophilin: the structure of bound methylcobalamin and a functional role in protecting methylcobalamin from photolysis. Biochemistry. 1993 Dec 21;32(50):13886-92. [PubMed:8268164 ]
  4. Suormala T, Baumgartner MR, Coelho D, Zavadakova P, Kozich V, Koch HG, Berghauser M, Wraith JE, Burlina A, Sewell A, Herwig J, Fowler B: The cblD defect causes either isolated or combined deficiency of methylcobalamin and adenosylcobalamin synthesis. J Biol Chem. 2004 Oct 8;279(41):42742-9. Epub 2004 Aug 2. [PubMed:15292234 ]
  5. Weinberg JB, Sauls DL, Misukonis MA, Shugars DC: Inhibition of productive human immunodeficiency virus-1 infection by cobalamins. Blood. 1995 Aug 15;86(4):1281-7. [PubMed:7632933 ]
  6. Murayama K, Katsumi T, Asai T: [Clinical evaluation of micturitional dysfunction after the operation for rectal cancer and effects of mecobalamin on that dysfunction]. Hinyokika Kiyo. 1989 Nov;35(11):1853-7. [PubMed:2694825 ]
  7. Ramsey RB, Scott T, Banik NL: Fatty acid composition of myelin isolated from the brain of a patient with cellular deficiency of co-enzyme forms of vitamin B12. J Neurol Sci. 1977 Nov;34(2):221-32. [PubMed:925711 ]
  8. van Kapel J, Spijkers LJ, Lindemans J, Abels J: Improved distribution analysis of cobalamins and cobalamin analogues in human plasma in which the use of thiol-blocking agents is a prerequisite. Clin Chim Acta. 1983 Jul 15;131(3):211-24. [PubMed:6883715 ]
  9. el Kholty S, Gueant JL, Bressler L, Djalali M, Boissel P, Gerard P, Nicolas JP: Portal and biliary phases of enterohepatic circulation of corrinoids in humans. Gastroenterology. 1991 Nov;101(5):1399-408. [PubMed:1936810 ]

Enzymes

General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91