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Record Information
Version1.0
Creation date2011-09-21 00:21:08 UTC
Update date2019-11-26 03:21:06 UTC
Primary IDFDB022886
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCobalamin
DescriptionCobalamin participates in two enzymatic processes in mammalian cells. In the methionine synthase (EC 2.1.1.13) reaction, homocysteine (HCys) is converted to methionine allowing for the "recycling" of 5-methyl-tetrahydrofolate (THF) to N5,10 methylene-THF which is needed for the de novo synthesis of thymidylic acid and ultimately, for DNA formation. Since conversion of N5,10-methylene-THF to N5-methyl-THF is irreversible, cobalamin deficiency "traps" folic acid as N5-methyl-THF. Concurrently, HCys accumulates while methionine decreases, leading to a decrease in S-adenosylmethionine which further limits N5,10-methylene-THF formation by decreasing the synthesis of formyl-THF ("formate starvation"). Decreased methionine and S-adenosylmethionine may limit many methylation reactions including those involving DNA and myelin basic protein. In the methylmalonyl CoA mutase (EC 5.1.99.1) reaction, methylmalonyl CoA, derived from propionic acid synthesized by intestinal bacteria, is converted to succinyl CoA, a precursor for fatty acid and heme synthesis Thus, cobalamin deficiency results in methylmalonic acid (MMA) accumulation. Cobalamin deficiency causes megaloblastic anemia and neurocognitive abnormalities but effects on immune function and bone formation have also been described. Low serum cobalamin levels increase the risk of osteoporosis. Tests for cobalamin deficiency include measurements of 1) total cobalamin; 2) MMA and HCys, as indices of functional cobalamin deficiency; and 3) holotranscobalamin as a measure of the metabolically active fraction of circulating cobalamin. Each approach has significant limitations. Moreover, since the pathogenesis of neurologic dysfunction in cobalamin deficiency remains unclear, these tests may not be reliable markers of neurocognitive impairment. Subtle cobalamin deficiency, defined as elevated metabolite levels usually in asymptomatic patients with low or normal serum cobalamin values, is prevalent in the elderly and has been associated with food cobalamin malabsorption, a disorder characterized by the inability to release vitamin B12 from food or from its binding proteins. Malabsorption is often unrecognized or not investigated. However, because of the potential seriousness of the complications, particularly neuropsychiatric and hematological investigation of all patients who present with vitamin or nutritional deficiency is required. Classic disorders, such as pernicious anemia, are the cause of cobalamin deficiency in only a limited proportion of elderly patients. Epidemiological studies have shown a prevalence of cobalamin deficiency of around 20% in the elderly population of industrialized countries (between 50% and 60%, depending on the definition of cobalamin deficiency used in the study). New routes of cobalamin administration (oral and nasal) are currently being developed, especially the use of oral cobalamin therapy to treat food-cobalamin malabsorption. (PMID: 16814909, 17822656) [HMDB]. Cobalamin is found in many foods, some of which are yellow bell pepper, green zucchini, sunburst squash (pattypan squash), and yellow wax bean.
CAS Number13408-78-1
Structure
Thumb
Synonyms
SynonymSource
5,6-Dimethyl-1-a-D-ribofuranosyl-1H-benzimidazoleHMDB
5,6-Dimethyl-1-a-D-ribofuranosylbenzimidazoleHMDB
5,6-Dimethyl-1-alpha-delta-ribofuranosyl-1H-benzimidazoleHMDB
5,6-Dimethyl-1-alpha-delta-ribofuranosylbenzimidazoleHMDB
Cob(III)alaminHMDB
Cobalamin (III)HMDB
CobalamineHMDB
Cobinamide ion(1+) dihydrogen phosphate (ester) inner salt 3'-esterHMDB
Cobinamide ion(1+) dihydrogen phosphate (ester) inner salt 3'-ester with 5,6-dimethyl-1-alpha-delta-ribofuranosyl-1H-benzimidazoleHMDB
HydroxominHMDB
RubiviteHMDB
Rubratope-57HMDB
Rubratope-60HMDB
RuviteHMDB
Vitamin b12HMDB
b 12, VitaminMeSH
b12, VitaminMeSH
CobalaminsMeSH
CyanocobalaminMeSH
EritronMeSH
Vitamin b 12MeSH
5,6-dimethyl-1-a-D-ribofuranosylbenzimidazolehmdb
5,6-dimethyl-1-alpha-delta-ribofuranosylbenzimidazolehmdb
Cobinamide ion(1+) dihydrogen ate (ester) inner salt 3'-esterHMDB
Cobinamide ion(1+) dihydrogen ate (ester) inner salt 3'-ester with 5,6-dimethyl-1-alpha-delta-ribofuranosyl-1H-benzimidazoleHMDB
Vitamin B12hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP2.93ALOGPS
logP1.11ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area479.79 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity430.84 m³·mol⁻¹ChemAxon
Polarizability134.49 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC62H88CoN13O14P
IUPAC namecobalt(3+) ion 1-(3-hydroxy-4-{[hydroxy({1-[(1-hydroxy-3-{8,13,18-tris[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]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-1lambda5,3-benzodiazol-1-ylium
InChI IdentifierInChI=1S/C62H90N13O14P.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);/q;+3/p-2
InChI KeyNSLAUEAQDBERRV-UHFFFAOYSA-L
Isomeric SMILES[Co+3].CC(CNC(=O)CCC1(C)C(CC(N)=O)C2[N-]\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=NC2(C)C(C)(CC(N)=O)C4CCC(N)=O)\C(C)(CC(N)=O)C3CCC(N)=O)/C(C)(C)C1CCC(N)=O)OP([O-])(=O)OC1C(CO)OC(C1O)N1C=NC2=C1C=C(C)C(C)=C2
Average Molecular Weight1329.3478
Monoisotopic Molecular Weight1328.564331295
Classification
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
  • 1-ribofuranosylbenzimidazole
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Benzenoid
  • Fatty amide
  • Fatty acyl
  • Pyrroline
  • Pyrrolidine
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Oxacycle
  • Azacycle
  • Organic transition metal salt
  • Carbene-type 1,3-dipolar compound
  • Carboxylic acid derivative
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Imine
  • Primary alcohol
  • Organic salt
  • Organic cobalt salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2031000095-b9bf39827ae83761ccb6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-2393000063-424c175511ddc5e4d2feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9740000051-7d6903b2dd8881008344Spectrum
NMRNot Available
ChemSpider ID4942647
ChEMBL IDNot Available
KEGG Compound IDC05776
Pubchem Compound ID6438156
Pubchem Substance IDNot Available
ChEBI ID28911
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02174
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCobalamin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Methylmalonyl-CoA mutase, mitochondrialMUTP22033
Methylmalonic aciduria type A protein, mitochondrialMMAAQ8IVH4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.