Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:04 UTC
HMDB IDHMDB0000607
Secondary Accession Numbers
  • HMDB0014263
  • HMDB00607
  • HMDB14263
Metabolite Identification
Common NameCyanocobalamin
DescriptionCyanocobalamin (commonly known as Vitamin B12) is the most chemically complex of all the vitamins. Cyanocobalamin's structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Cyanocobalamin cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of cyanocobalamin are bacteria and archaea. Higher plants do not concentrate cyanocobalamin from the soil and so are a poor source of the substance as compared with animal tissues. Cyanocobalamin is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products.
Structure
Data?1582752143
Synonyms
ValueSource
AnacobinHMDB
BerubigenHMDB
Betalin 12 crystallineHMDB
Betaline-12HMDB
BetolvexHMDB
BevidoxHMDB
Bevidox concentrateHMDB
BiocobalamineHMDB
ByladoceHMDB
Cabadon mHMDB
Cobadoce forteHMDB
CobalinHMDB
CobaviteHMDB
Copharvit 5000HMDB
CovitHMDB
CrystaminHMDB
CrystamineHMDB
CrystiminHMDB
CrystwelHMDB
Cyano-b12HMDB
Cyanobalamin concentrateHMDB
Cyanocob(III)alaminHMDB
Cyanocobalamin (JP15/usp)HMDB
CyanocobalamineHMDB
CyanocobalminHMDB
CycobeminHMDB
CycolaminHMDB
CykobeminHMDB
CykobeminetHMDB
CyominHMDB
CyredinHMDB
CytaconHMDB
CytamenHMDB
CytobionHMDB
DepinarHMDB
DicopacHMDB
DimethylbenzimidazoylcobamideHMDB
DistivitHMDB
DocemineHMDB
DocibinHMDB
DocivitHMDB
DodecabeeHMDB
DodecaviteHMDB
DodexHMDB
DuodecibinHMDB
EmbiolHMDB
EmociclinaHMDB
EritroneHMDB
ErycytolHMDB
ErythrotinHMDB
EuhaemonHMDB
Extrinsic factorHMDB
Factor IIHMDB
FerminHMDB
FresminHMDB
HemominHMDB
HepagonHMDB
HepavisHMDB
HepcoviteHMDB
Hylugel plusHMDB
Lactobacillus lactis dorner factorHMDB
MacrabinHMDB
MegabionHMDB
MegalovelHMDB
MilbedoceHMDB
MillevitHMDB
NagravonHMDB
NascobalHMDB
NormocytinHMDB
NovidroxinHMDB
PernaemonHMDB
PernaevitHMDB
PernipuronHMDB
PlecyaminHMDB
PoyaminHMDB
RebraminHMDB
RedaminaHMDB
RedisolHMDB
RhodacrystHMDB
RubesolHMDB
RubraminHMDB
RubripcaHMDB
RubrocitolHMDB
SytobexHMDB
VibaltHMDB
VibisoneHMDB
VirubraHMDB
Vita-rubraHMDB
Vitamin b12HMDB
Vitamin b12 complexHMDB
Vitamin b12 preparationHMDB
VitarubinHMDB
VitralHMDB
Chemical FormulaC63H89CoN14O14P
Average Molecular Weight1356.3731
Monoisotopic Molecular Weight1355.575230332
IUPAC Namecyanocobalamin
Traditional Namecyanocobalamin
CAS Registry Number68-19-9
SMILES
[H][C@@](C)(CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)[C@@]2([H])N([Co]C#N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)\[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)/C(C)(C)[C@@H]1CCC(N)=O)OP(O)(=O)O[C@@H]1[C@@H](CO)O[C@@H]([C@@H]1O)N1C=NC2=CC(C)=C(C)C=C12
InChI Identifier
InChI=1S/C62H90N13O14P.CN.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;1-2;/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;;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
InChI KeySEKGMJVHSBBHRD-WZHZPDAFSA-M
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
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Monosaccharide
  • Fatty acyl
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Fatty amide
  • Phosphoric acid ester
  • Benzenoid
  • Alkyl phosphate
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Pyrrolidine
  • Pyrroline
  • Tetrahydrofuran
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketimine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Organic metal salt
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Transition metal cyanide salt
  • Organic transition metal salt
  • Organic salt
  • Hydrocarbon derivative
  • Organic transition metal moeity
  • Imine
  • Organometallic compound
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.5 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.87ALOGPS
logS-4.6ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)13.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area487.61 ŲChemAxon
Polarizability137.36 ųChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 10V, Positive-QTOFsplash10-0002-2505000009-edb77b0741ab131f8e9c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 20V, Positive-QTOFsplash10-0002-2903000005-7209eb5b1abfc27349e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 40V, Positive-QTOFsplash10-0002-2920000004-63934a026bb66dd6d2f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 10V, Negative-QTOFsplash10-03dj-4319000001-284fb8fc72f8ccc631962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 20V, Negative-QTOFsplash10-0002-0912000001-6cad42b357edecf064952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 40V, Negative-QTOFsplash10-002b-7900000000-d146eb8a599bacc809542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 10V, Negative-QTOFsplash10-0udi-0009000000-0fc6a488f1be9c4178282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 20V, Negative-QTOFsplash10-0zmi-2097000000-ff8aea846c78c61c88492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 40V, Negative-QTOFsplash10-007a-9500000000-229e183ee286be69cc432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 10V, Positive-QTOFsplash10-052s-0019000002-5c7fd3769fbb6bde0dd52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 20V, Positive-QTOFsplash10-08g0-1097000000-a17c21bdb2ecc6da86102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanocobalamin 40V, Positive-QTOFsplash10-01em-4890000011-4fe6c6d7508c45900ce62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • All Tissues
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified>0.000120 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000316 +/- 0.000128 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000316 +/- 0.00008790 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000319 +/- 0.000168 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000320 +/- 0.000192 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000410 +/- 0.000160 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000422 +/- 0.000179 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000448 +/- 0.000164 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000450 +/- 0.000283 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000459 +/- 0.000355 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000488 +/- 0.000445 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000524 +/- 0.000623 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000570 +/- 0.000641 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000245 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000281 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.000349 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.000399 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000524 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000276 +/- 0.000137 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000294 +/- 0.000150 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000312 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000315 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000318 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000321 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000346 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000356 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000358 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000363 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00038 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000244 +/- 0.000132 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000280 +/- 0.000151 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.000479 +/- 0.000234 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00037 (0.00009-0.00155) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00025 +/- 0.00008 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0002385 +/- 0.0000991 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00013 (0.00004-0.00050) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00028 +/- 0.00012 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0003 +/- 0.0001 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.000142 - 0.000724 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000016 +/- 0.0000057 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000006 +/- 0.000002 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000001733 +/- 0.000001 umol/mmol creatinineChildren (1 - 13 years old)Both
Normal
details
UrineDetected and Quantified0.000001867 +/- 0.000001200 umol/mmol creatinineChildren (1 - 13 years old)Both
Normal
details
UrineDetected and Quantified0.000002267 +/- 0.000002333 umol/mmol creatinineChildren (1 - 13 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000120 uMAdult (>18 years old)BothVitamin B12 deficiency details
BloodDetected and Quantified0.00055 +/- 0.00041 uMAdult (>18 years old)BothHomozygous sickle cell disease details
BloodDetected and Quantified0.000198 +/- 0.00007299 uMAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease References
Homozygous sickle cell disease
  1. van der Dijs FP, Schnog JJ, Brouwer DA, Velvis HJ, van den Berg GA, Bakker AJ, Duits AJ, Muskiet FD, Muskiet FA: Elevated homocysteine levels indicate suboptimal folate status in pediatric sickle cell patients. Am J Hematol. 1998 Nov;59(3):192-8. [PubMed:9798656 ]
Pregnancy
  1. Shiraishi M, Haruna M, Matsuzaki M, Murayama R, Sasaki S, Murashima S: Validity and reproducibility of folate and vitamin B(12) intakes estimated from a self-administered diet history questionnaire in Japanese pregnant women. Nutr J. 2012 Mar 15;11:15. doi: 10.1186/1475-2891-11-15. [PubMed:22420377 ]
Vitamin B12 deficiency
  1. Brito A, Grapov D, Fahrmann J, Harvey D, Green R, Miller JW, Fedosov SN, Shahab-Ferdows S, Hampel D, Pedersen TL, Fiehn O, Newman JW, Uauy R, Allen LH: The Human Serum Metabolome of Vitamin B-12 Deficiency and Repletion, and Associations with Neurological Function in Elderly Adults. J Nutr. 2017 Aug 9. pii: jn.117.248278. doi: 10.3945/jn.117.248278. [PubMed:28794205 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013264
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02823
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyanocobalamin
METLIN ID5582
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17439
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000199
Good Scents IDNot Available
References
Synthesis ReferenceGardner, N.; Champagne, C. P. Production of Propionibacterium shermanii biomass and vitamin B12 on spent media. Journal of Applied Microbiology (2005), 99(5), 1236-1245.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Cupp MS, Zhang D, Cupp EW: Horn fly (Diptera: Muscidae) saliva targets thrombin action in hemostasis. J Med Entomol. 2000 May;37(3):416-21. [PubMed:15535586 ]
  2. Waters RS, Bryden NA, Patterson KY, Veillon C, Anderson RA: EDTA chelation effects on urinary losses of cadmium, calcium, chromium, cobalt, copper, lead, magnesium, and zinc. Biol Trace Elem Res. 2001 Dec;83(3):207-21. [PubMed:11794513 ]
  3. Reznichenko AM, Fesenko VP, Shestopalov DV, Tatarchuk PA: [Changes in cell immunity indexes under the influence of thymalin, thyroxine and fibronectin in patients with hyperplastic diseases of thyroid gland before and after the surgery]. Klin Khir. 2001 Dec;(12):31-3. [PubMed:11944270 ]
  4. Hermann K, Rittweger R, Ring J: Urinary excretion of angiotensin I, II, arginine vasopressin and oxytocin in patients with anaphylactoid reactions. Clin Exp Allergy. 1992 Sep;22(9):845-53. [PubMed:1422942 ]
  5. Nilsson-Ehle H, Jagenburg R, Landahl S, Lindstedt G, Swolin B, Westin J: Cyanocobalamin absorption in the elderly: results for healthy subjects and for subjects with low serum cobalamin concentration. Clin Chem. 1986 Jul;32(7):1368-71. [PubMed:3719947 ]
  6. Sesso RM, Iunes Y, Melo AC: Myeloneuropathy following nitrous oxide anesthaesia in a patient with macrocytic anaemia. Neuroradiology. 1999 Aug;41(8):588-90. [PubMed:10447571 ]
  7. Authors unspecified: No evidence of association between prothrombotic gene polymorphisms and the development of acute myocardial infarction at a young age. Circulation. 2003 Mar 4;107(8):1117-22. [PubMed:12615788 ]
  8. Oh Y, Beukers MW, Pham HM, Smanik PA, Smith MC, Rosenfeld RG: Altered affinity of insulin-like growth factor II (IGF-II) for receptors and IGF-binding proteins, resulting from limited modifications of the IGF-II molecule. Biochem J. 1991 Aug 15;278 ( Pt 1):249-54. [PubMed:1715685 ]
  9. Hoffer LJ, Saboohi F, Golden M, Barre PE: Cobalamin dose regimen for maximum homocysteine reduction in end-stage renal disease. Metabolism. 2005 Jun;54(6):835-40. [PubMed:15931623 ]
  10. Hohlagschwandtner M, Unfried G, Heinze G, Huber JC, Nagele F, Tempfer C: Combined thrombophilic polymorphisms in women with idiopathic recurrent miscarriage. Fertil Steril. 2003 May;79(5):1141-8. [PubMed:12738509 ]
  11. Pittock SJ, Payne TA, Harper CM: Reversible myelopathy in a 34-year-old man with vitamin B12 deficiency. Mayo Clin Proc. 2002 Mar;77(3):291-4. [PubMed:11888035 ]
  12. Houeto P, Buneaux F, Galliot-Guilley M, Baud FJ, Levillain P: Determination of hydroxocobalamin and cyanocobalamin by derivative spectrophotometry in cyanide poisoning. J Anal Toxicol. 1994 May-Jun;18(3):154-8. [PubMed:8065126 ]
  13. Manier JW, Beltaos E: Benign gastric ulcer in a patient with pernicious anemia. Gastroenterology. 1975 Sep;69(3):744-5. [PubMed:1158091 ]
  14. Mayer G, Kroger M, Meier-Ewert K: Effects of vitamin B12 on performance and circadian rhythm in normal subjects. Neuropsychopharmacology. 1996 Nov;15(5):456-64. [PubMed:8914118 ]
  15. Lao JI, Montoriol C, Morer I, Beyer K: Genetic contribution to aging: deleterious and helpful genes define life expectancy. Ann N Y Acad Sci. 2005 Dec;1057:50-63. [PubMed:16399887 ]
  16. Baumann H, Muller-Eberhard U: Synthesis of hemopexin and cysteine protease inhibitor is coordinately regulated by HSF-II and interferon-beta 2 in rat hepatoma cells. Biochem Biophys Res Commun. 1987 Aug 14;146(3):1218-28. [PubMed:3304291 ]
  17. Houeto P, Hoffman JR, Imbert M, Levillain P, Baud FJ: Relation of blood cyanide to plasma cyanocobalamin concentration after a fixed dose of hydroxocobalamin in cyanide poisoning. Lancet. 1995 Sep 2;346(8975):605-8. [PubMed:7651005 ]
  18. van Asselt DZ, van den Broek WJ, Lamers CB, Corstens FH, Hoefnagels WH: Free and protein-bound cobalamin absorption in healthy middle-aged and older subjects. J Am Geriatr Soc. 1996 Aug;44(8):949-53. [PubMed:8708306 ]
  19. Wu H, Bruley DF: Homologous human blood protein separation using immobilized metal affinity chromatography: protein C separation from prothrombin with application to the separation of factor IX and prothrombin. Biotechnol Prog. 1999 Sep-Oct;15(5):928-31. [PubMed:10514264 ]
  20. Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [PubMed:3295013 ]
  21. Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [PubMed:8534956 ]
  22. Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [PubMed:11863489 ]
  23. Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [PubMed:12390080 ]
  24. Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. [PubMed:14616423 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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
References
  1. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [PubMed:19904199 ]
  2. Allen LH: Causes of vitamin B12 and folate deficiency. Food Nutr Bull. 2008 Jun;29(2 Suppl):S20-34; discussion S35-7. [PubMed:18709879 ]
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
References
  1. Nakamura T, Saionji K, Hiejima Y, Hirayama H, Tago K, Takano H, Tajiri M, Hayashi K, Kawabata M, Funamizu M, Makita Y, Hata A: Methylenetetrahydrofolate reductase genotype, vitamin B12, and folate influence plasma homocysteine in hemodialysis patients. Am J Kidney Dis. 2002 May;39(5):1032-9. [PubMed:11979347 ]
  2. Erdogan MO, Yildiz SH, Solak M, Eser O, Cosar E, Eser B, Koken R, Buyukbas S: C677T polymorphism of the methylenetetrahydrofolate reductase gene does not affect folic acid, vitamin B12, and homocysteine serum levels in Turkish children with neural tube defects. Genet Mol Res. 2010 Jun 22;9(2):1197-203. doi: 10.4238/vol9-2gmr816. [PubMed:20589617 ]
General function:
Involved in isomerase activity
Specific function:
Involved in the degradation of several amino acids, odd-chain fatty acids and cholesterol via propionyl-CoA to the tricarboxylic acid cycle. MCM has different functions in other species.
Gene Name:
MUT
Uniprot ID:
P22033
Molecular weight:
83133.755
References
  1. Worgan LC, Niles K, Tirone JC, Hofmann A, Verner A, Sammak A, Kucic T, Lepage P, Rosenblatt DS: Spectrum of mutations in mut methylmalonic acidemia and identification of a common Hispanic mutation and haplotype. Hum Mutat. 2006 Jan;27(1):31-43. [PubMed:16281286 ]
  2. Brooks AJ, Vlasie M, Banerjee R, Brunold TC: Co-C bond activation in methylmalonyl-CoA mutase by stabilization of the post-homolysis product Co2+ cobalamin. J Am Chem Soc. 2005 Nov 30;127(47):16522-8. [PubMed:16305240 ]
  3. Kozlowski PM, Andruniow T, Jarzecki AA, Zgierski MZ, Spiro TG: DFT analysis of co-alkyl and co-adenosyl vibrational modes in B12-cofactors. Inorg Chem. 2006 Jul 10;45(14):5585-90. [PubMed:16813422 ]
  4. Moras E, Hosack A, Watkins D, Rosenblatt DS: Mitochondrial vitamin B12-binding proteins in patients with inborn errors of cobalamin metabolism. Mol Genet Metab. 2007 Feb;90(2):140-7. Epub 2006 Sep 29. [PubMed:17011224 ]
  5. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [PubMed:19904199 ]
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the reductive regeneration of cob(I)alamin cofactor required for the maintenance of methionine synthase in a functional state.
Gene Name:
MTRR
Uniprot ID:
Q9UBK8
Molecular weight:
77672.995
References
  1. O'Leary VB, Mills JL, Pangilinan F, Kirke PN, Cox C, Conley M, Weiler A, Peng K, Shane B, Scott JM, Parle-McDermott A, Molloy AM, Brody LC: Analysis of methionine synthase reductase polymorphisms for neural tube defects risk association. Mol Genet Metab. 2005 Jul;85(3):220-7. Epub 2005 Mar 17. [PubMed:15979034 ]
  2. Gueant-Rodriguez RM, Juilliere Y, Candito M, Adjalla CE, Gibelin P, Herbeth B, Van Obberghen E, Gueant JL: Association of MTRRA66G polymorphism (but not of MTHFR C677T and A1298C, MTRA2756G, TCN C776G) with homocysteine and coronary artery disease in the French population. Thromb Haemost. 2005 Sep;94(3):510-5. [PubMed:16268464 ]
  3. Miriuka SG, Langman LJ, Evrovski J, Miner SE, D'Mello N, Delgado DH, Wong BY, Ross HJ, Cole DE: Genetic polymorphisms predisposing to hyperhomocysteinemia in cardiac transplant patients. Transpl Int. 2005 Jan;18(1):29-35. [PubMed:15612980 ]
  4. Berkun Y, Abou Atta I, Rubinow A, Orbach H, Levartovsky D, Aamar S, Arbel O, Dresner-Pollak R, Friedman G, Ben-Yehuda A: 2756GG genotype of methionine synthase reductase gene is more prevalent in rheumatoid arthritis patients treated with methotrexate and is associated with methotrexate-induced nodulosis. J Rheumatol. 2007 Aug;34(8):1664-9. Epub 2007 Jul 1. [PubMed:17611986 ]
  5. van der Linden IJ, den Heijer M, Afman LA, Gellekink H, Vermeulen SH, Kluijtmans LA, Blom HJ: The methionine synthase reductase 66A>G polymorphism is a maternal risk factor for spina bifida. J Mol Med (Berl). 2006 Dec;84(12):1047-54. Epub 2006 Oct 6. [PubMed:17024475 ]
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
References
  1. Zhang J, Dobson CM, Wu X, Lerner-Ellis J, Rosenblatt DS, Gravel RA: Impact of cblB mutations on the function of ATP:cob(I)alamin adenosyltransferase in disorders of vitamin B12 metabolism. Mol Genet Metab. 2006 Apr;87(4):315-22. Epub 2006 Jan 24. [PubMed:16439175 ]
  2. Lerner-Ellis JP, Gradinger AB, Watkins D, Tirone JC, Villeneuve A, Dobson CM, Montpetit A, Lepage P, Gravel RA, Rosenblatt DS: Mutation and biochemical analysis of patients belonging to the cblB complementation class of vitamin B12-dependent methylmalonic aciduria. Mol Genet Metab. 2006 Mar;87(3):219-25. Epub 2006 Jan 10. [PubMed:16410054 ]
General function:
Involved in nucleotide binding
Specific function:
Probable GTPase. May function as chaperone. May be involved in the transport of cobalamin (Cbl) into mitochondria for the final steps of adenosylcobalamin (AdoCbl) synthesis
Gene Name:
MMAA
Uniprot ID:
Q8IVH4
Molecular weight:
46537.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Lerner-Ellis JP, Dobson CM, Wai T, Watkins D, Tirone JC, Leclerc D, Dore C, Lepage P, Gravel RA, Rosenblatt DS: Mutations in the MMAA gene in patients with the cblA disorder of vitamin B12 metabolism. Hum Mutat. 2004 Dec;24(6):509-16. [PubMed:15523652 ]
  4. Dobson CM, Gradinger A, Longo N, Wu X, Leclerc D, Lerner-Ellis J, Lemieux M, Belair C, Watkins D, Rosenblatt DS, Gravel RA: Homozygous nonsense mutation in the MCEE gene and siRNA suppression of methylmalonyl-CoA epimerase expression: a novel cause of mild methylmalonic aciduria. Mol Genet Metab. 2006 Aug;88(4):327-33. Epub 2006 May 11. [PubMed:16697227 ]
General function:
Involved in cobalamin binding
Specific function:
May be involved in the binding and intracellular trafficking of cobalamin (vitamin B12)
Gene Name:
MMACHC
Uniprot ID:
Q9Y4U1
Molecular weight:
31728.1
References
  1. Chandler RJ, Aswani V, Tsai MS, Falk M, Wehrli N, Stabler S, Allen R, Sedensky M, Kazazian HH, Venditti CP: Propionyl-CoA and adenosylcobalamin metabolism in Caenorhabditis elegans: evidence for a role of methylmalonyl-CoA epimerase in intermediary metabolism. Mol Genet Metab. 2006 Sep-Oct;89(1-2):64-73. Epub 2006 Jul 14. [PubMed:16843692 ]
  2. Ben-Omran TI, Wong H, Blaser S, Feigenbaum A: Late-onset cobalamin-C disorder: a challenging diagnosis. Am J Med Genet A. 2007 May 1;143A(9):979-84. [PubMed:17431913 ]
  3. Morel CF, Lerner-Ellis JP, Rosenblatt DS: Combined methylmalonic aciduria and homocystinuria (cblC): phenotype-genotype correlations and ethnic-specific observations. Mol Genet Metab. 2006 Aug;88(4):315-21. Epub 2006 May 22. [PubMed:16714133 ]
  4. Lerner-Ellis JP, Tirone JC, Pawelek PD, Dore C, Atkinson JL, Watkins D, Morel CF, Fujiwara TM, Moras E, Hosack AR, Dunbar GV, Antonicka H, Forgetta V, Dobson CM, Leclerc D, Gravel RA, Shoubridge EA, Coulton JW, Lepage P, Rommens JM, Morgan K, Rosenblatt DS: Identification of the gene responsible for methylmalonic aciduria and homocystinuria, cblC type. Nat Genet. 2006 Jan;38(1):93-100. Epub 2005 Nov 27. [PubMed:16311595 ]

Transporters

General function:
Involved in cobalamin binding
Specific function:
Primary vitamin B12-binding and transport protein. Delivers cobalamin to cells
Gene Name:
TCN2
Uniprot ID:
P20062
Molecular weight:
47534.5
References
  1. Chen X, Remacha AF, Sarda MP, Carmel R: Influence of cobalamin deficiency compared with that of cobalamin absorption on serum holo-transcobalamin II. Am J Clin Nutr. 2005 Jan;81(1):110-4. [PubMed:15640468 ]
  2. Alessio AC, Hoehr NF, Siqueira LH, Bydlowski SP, Annichino-Bizzacchi JM: Polymorphism C776G in the transcobalamin II gene and homocysteine, folate and vitamin B12 concentrations. Association with MTHFR C677T and A1298C and MTRR A66G polymorphisms in healthy children. Thromb Res. 2007;119(5):571-7. Epub 2006 Jul 3. [PubMed:16820193 ]
  3. Bowen RA, Drake SK, Vanjani R, Huey ED, Grafman J, Horne MK 3rd: Markedly increased vitamin B12 concentrations attributable to IgG-IgM-vitamin B12 immune complexes. Clin Chem. 2006 Nov;52(11):2107-14. [PubMed:17068171 ]
  4. Bosco P, Gueant-Rodriguez RM, Anello G, Spada R, Romano A, Fajardo A, Caraci F, Ferri R, Gueant JL: Association of homocysteine (but not of MTHFR 677 C>T, MTR 2756 A>G, MTRR 66 A>G and TCN2 776 C>G) with ischaemic cerebrovascular disease in Sicily. Thromb Haemost. 2006 Aug;96(2):154-9. [PubMed:16894458 ]
  5. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053 ]
General function:
Involved in cobalamin binding
Specific function:
Vitamin B12-binding protein. Transports cobalamin into cells
Gene Name:
TCN1
Uniprot ID:
P20061
Molecular weight:
48206.3
References
  1. Carmel R: Haptocorrin (transcobalamin I) and cobalamin deficiencies. Clin Chem. 2007 Feb;53(2):367-8; author reply 368-9. [PubMed:17259255 ]
  2. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053 ]
General function:
Involved in cobalamin binding
Specific function:
Promotes absorption of the essential vitamin cobalamin (Cbl) in the ileum by specific receptor-mediated endocytosis
Gene Name:
GIF
Uniprot ID:
P27352
Molecular weight:
45415.7
References
  1. Fedosov SN, Fedosova NU, Berglund L, Moestrup SK, Nexo E, Petersen TE: Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor. Biochemistry. 2005 Mar 8;44(9):3604-14. [PubMed:15736970 ]
  2. He Q, Madsen M, Kilkenney A, Gregory B, Christensen EI, Vorum H, Hojrup P, Schaffer AA, Kirkness EF, Tanner SM, de la Chapelle A, Giger U, Moestrup SK, Fyfe JC: Amnionless function is required for cubilin brush-border expression and intrinsic factor-cobalamin (vitamin B12) absorption in vivo. Blood. 2005 Aug 15;106(4):1447-53. Epub 2005 Apr 21. [PubMed:15845892 ]
  3. Moestrup SK: New insights into carrier binding and epithelial uptake of the erythropoietic nutrients cobalamin and folate. Curr Opin Hematol. 2006 May;13(3):119-23. [PubMed:16567952 ]
General function:
Involved in calcium ion binding
Specific function:
Cotransporter which plays a role in lipoprotein, vitamin and iron metabolism, by facilitating their uptake. Binds to ALB, MB, Kappa and lambda-light chains, TF, hemoglobin, GC, SCGB1A1, APOA1, high density lipoprotein, and the GIF-cobalamin complex. The binding of all ligands required calcium. Serves as important transporter in several absorptive epithelia, including intestine, renal proximal tubules and embryonic yolk sac. Interaction with LRP2 mediates its trafficking throughout vesicles and facilitates the uptake of specific ligands like GC, hemoglobin, ALB, TF and SCGB1A1. Interaction with AMN controls its trafficking to the plasma membrane and facilitates endocytosis of ligands. May play an important role in the development of the peri-implantation embryo through internalization of APOA1 and cholesterol. Binds to LGALS3 at the maternal-fetal interface
Gene Name:
CUBN
Uniprot ID:
O60494
Molecular weight:
398672.8
References
  1. Fedosov SN, Fedosova NU, Berglund L, Moestrup SK, Nexo E, Petersen TE: Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor. Biochemistry. 2005 Mar 8;44(9):3604-14. [PubMed:15736970 ]
  2. He Q, Madsen M, Kilkenney A, Gregory B, Christensen EI, Vorum H, Hojrup P, Schaffer AA, Kirkness EF, Tanner SM, de la Chapelle A, Giger U, Moestrup SK, Fyfe JC: Amnionless function is required for cubilin brush-border expression and intrinsic factor-cobalamin (vitamin B12) absorption in vivo. Blood. 2005 Aug 15;106(4):1447-53. Epub 2005 Apr 21. [PubMed:15845892 ]
  3. Moestrup SK: New insights into carrier binding and epithelial uptake of the erythropoietic nutrients cobalamin and folate. Curr Opin Hematol. 2006 May;13(3):119-23. [PubMed:16567952 ]
General function:
Involved in multicellular organismal development
Specific function:
Necessary for efficient absorption of vitamin B12. May direct the production of trunk mesoderm during development by modulating a bone morphogenetic protein (BMP) signaling pathway in the underlying visceral endoderm
Gene Name:
AMN
Uniprot ID:
Q9BXJ7
Molecular weight:
47753.9
References
  1. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053 ]

Only showing the first 10 proteins. There are 12 proteins in total.