Cobalamin (CHEM035354)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:41:09 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035354
Identification
Common NameCobalamin
ClassSmall Molecule
DescriptionA cobalamin in which the central cobalt atom has an oxidation state of +3.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-(5,6-Dimethylbenzimidazolyl)cobamideChEBI
CblChEBI
Cobalamin (III)ChEBI
Cobalamin(1+)ChEBI
Cobalamin(III)ChEBI
a-(5,6-Dimethylbenzimidazolyl)cobamideGenerator
Α-(5,6-dimethylbenzimidazolyl)cobamideGenerator
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
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, VitaminHMDB
b12, VitaminHMDB
CobalaminsHMDB
CyanocobalaminHMDB
EritronHMDB
Vitamin b 12HMDB
Chemical FormulaC62H88CoN13O14P
Average Molecular Mass1329.348 g/mol
Monoisotopic Mass1328.564 g/mol
CAS Registry Number13408-78-1
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)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-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-diuid-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)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-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-diuid-15-olate
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
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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP0.61ALOGPS
logP-14ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-0.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area417 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity337.47 m³·mol⁻¹ChemAxon
Polarizability132.05 ųChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2031000095-b9bf39827ae83761ccb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-2393000063-424c175511ddc5e4d2feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9740000051-7d6903b2dd8881008344Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0059000000-dec49680276dd7d5a080Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i00-0092000000-2a13d3fd995ffd79ff7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3191000000-20e008a7f11bbe916e61Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002174
FooDB IDFDB022886
Phenol Explorer IDNot Available
KNApSAcK IDC00001534
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6527
PDB IDNot Available
Wikipedia LinkCobalamin
Chemspider ID5256728
ChEBI ID28911
PubChem Compound ID6857388
Kegg Compound IDC05776
YMDB IDYMDB16147
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Abou-Zeid, A. A.; El-Sherbeeny, M. R. Production of cobalamin by Streptomyces olivaceus. Indian Journal of Technology (1976), 14(7), 357-9.
2. Fyfe JC, Madsen M, Hojrup P, Christensen EI, Tanner SM, de la Chapelle A, He Q, Moestrup SK: The functional cobalamin (vitamin B12)-intrinsic factor receptor is a novel complex of cubilin and amnionless. Blood. 2004 Mar 1;103(5):1573-9. Epub 2003 Oct 23.
3. Urban G, Pietrzik K, Hotzel D: [Radiological investigations of cobalamin supply with regard to folate status (author's transl)]. Int J Vitam Nutr Res. 1981;51(2):124-31.
4. Kanazawa S, Herbert V: Total corrinoid, cobalamin (vitamin B12), and cobalamin analogue levels may be normal in serum despite cobalamin in liver depletion in patients with alcoholism. Lab Invest. 1985 Jul;53(1):108-10.
5. Minato H, Inada A, Kozaka S: [The effect of the external biliary diversion on cobalamin functions]. Nihon Geka Gakkai Zasshi. 1995 Oct;96(10):695-702.
6. Hansen PK, Byskov J, Gimsing P, Hippe E, Ladefoged K: Cobalamin absorption determined by the stool spot test. Reliability in patients with uremia or disorders of the ileum. Scand J Gastroenterol. 1986 Apr;21(3):341-7.
7. Ermens AA, Vlasveld LT, van Marion-Kievit JA, Lensen CJ, Lindemans J: [The significance of an elevated cobalamin concentration in the blood]. Ned Tijdschr Geneeskd. 2002 Mar 9;146(10):459-64.
8. Lott WB, Takyar SS, Tuppen J, Crawford DH, Harrison M, Sloots TP, Gowans EJ: Vitamin B12 and hepatitis C: molecular biology and human pathology. Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):4916-21. Epub 2001 Apr 10.
9. Haltmayer M, Mueller T, Poelz W: Erythrocyte mean cellular volume and its relation to serum homocysteine, vitamin B12 and folate. Acta Med Austriaca. 2002;29(2):57-60.
10. Baker H, Leevy CB, DeAngelis B, Frank O, Baker ER: Cobalamin (vitamin B12) and holotranscobalamin changes in plasma and liver tissue in alcoholics with liver disease. J Am Coll Nutr. 1998 Jun;17(3):235-8.
11. Watkins D, Matiaszuk N, Rosenblatt DS: Complementation studies in the cblA class of inborn error of cobalamin metabolism: evidence for interallelic complementation and for a new complementation class (cblH). J Med Genet. 2000 Jul;37(7):510-3.
12. Ermens AA, Vlasveld LT, Lindemans J: Significance of elevated cobalamin (vitamin B12) levels in blood. Clin Biochem. 2003 Nov;36(8):585-90.
13. Solomon LR: Disorders of cobalamin (vitamin B12) metabolism: emerging concepts in pathophysiology, diagnosis and treatment. Blood Rev. 2007 May;21(3):113-30. Epub 2006 Jul 11.
14. Andres E, Vidal-Alaball J, Federici L, Loukili NH, Zimmer J, Kaltenbach G: Clinical aspects of cobalamin deficiency in elderly patients. Epidemiology, causes, clinical manifestations, and treatment with special focus on oral cobalamin therapy. Eur J Intern Med. 2007 Oct;18(6):456-62. Epub 2007 Jul 12.