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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2019-07-23 05:45:26 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
Data?1563860726
Synonyms
ValueSource
CO-METHYLCOBALAMINChEBI
MeCblChEBI
MecobalaminChEBI
Methylcob(III)alaminChEBI
Methyl(III)cobalaminHMDB
Chemical FormulaC63H91CoN13O14P
Average Molecular Weight1344.3823
Monoisotopic Molecular Weight1343.587806391
IUPAC Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-1,5,6,17,23,28,31,31,36,38,41,42-dodecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
Traditional Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-1,5,6,17,23,28,31,31,36,38,41,42-dodecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
CAS Registry Number13422-55-4
SMILES
C1(CC[C@@]2([C@@H](CC(N)=O)[C@@]3([C@@]4([N+]5=C([C@H]([C@@]4(CC(N)=O)C)CCC(N)=O)C(C)=C4[N+]6=C(C=C7[N+]8=C([C@H](C7(C)C)CCC(N)=O)C(C)=C2N3[Co-3]568([N+]2=CN([C@H]3O[C@@H]([C@@H](OP(O[C@@H](CN1)C)([O-])=O)[C@H]3O)CO)C1=CC(C)=C(C=C21)C)C)[C@H]([C@@]4(CC(N)=O)C)CCC(N)=O)C)[H])C)=O
InChI Identifier
InChI=1S/C62H90N13O14P.CH3.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);1H3;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
InChI KeyJEWJRMKHSMTXPP-WZHZPDAFSA-L
Chemical Taxonomy
Description 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
  • Pentose phosphate
  • Monosaccharide phosphate
  • Benzimidazole
  • Benzenoid
  • Fatty amide
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Fatty acyl
  • Monosaccharide
  • Pyrrolidine
  • Pyrroline
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxylic acid derivative
  • Oxacycle
  • Metalloheterocycle
  • Azacycle
  • Organic metal salt
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic salt
  • Alcohol
  • Organic transition metal moeity
  • Organometallic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Transition metal alkyl
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

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-14ChemAxon
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-0.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area417 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity342.79 m³·mol⁻¹ChemAxon
Polarizability135.93 ųChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0009000000-270ebe7bf52ebc393bc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-0009000000-837bcde718484550d5d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-0009000000-9cdd3a31b906175760adJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f95-0089000000-105b8165c01a315a1c06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ke9-0049000000-874b2f636228deaa8738JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-0090000000-8fa0175ad99d0f3bcd2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0089000000-010c91e5b4f5bcb69026JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adj-1094000000-c827499f8629edca78e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7092000000-cfd079b185ddc58fcf85JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Fibroblasts
  • Myelin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.000220 +/- 0.00008410 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.000221 +/- 0.00008983 uMAdult (>18 years old)Not Specifiedfibromyalgia details
Associated Disorders and Diseases
Disease References
Fibromyalgia
  1. Ortancil O, Sanli A, Eryuksel R, Basaran A, Ankarali H: Association between serum ferritin level and fibromyalgia syndrome. Eur J Clin Nutr. 2010 Mar;64(3):308-12. doi: 10.1038/ejcn.2009.149. Epub 2010 Jan 20. [PubMed:20087382 ]
Associated OMIM IDsNone
DrugBank IDDB03614
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022939
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylcobalamin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28115
Food Biomarker OntologyNot Available
VMH IDNot Available
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