Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-07-24 17:50:11 UTC
HMDB IDHMDB00607
Secondary Accession Numbers
  • 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
Thumb
Synonyms
  1. Anacobin
  2. Berubigen
  3. Betalin 12 Crystalline
  4. Betaline-12
  5. Betolvex
  6. Bevidox
  7. Bevidox concentrate
  8. Biocobalamine
  9. Byladoce
  10. Cabadon m
  11. Cobadoce forte
  12. Cobalin
  13. Cobavite
  14. Copharvit 5000
  15. Covit
  16. Crystamin
  17. Crystamine
  18. Crystimin
  19. Crystwel
  20. Cyano-B12
  21. Cyanobalamin concentrate
  22. Cyanocob(III)alamin
  23. Cyanocobalamin (JP15/USP)
  24. Cyanocobalamine
  25. Cyanocobalmin
  26. Cycobemin
  27. Cycolamin
  28. Cykobemin
  29. Cykobeminet
  30. Cyomin
  31. Cyredin
  32. Cytacon
  33. Cytamen
  34. Cytobion
  35. Depinar
  36. Dicopac
  37. Dimethylbenzimidazoylcobamide
  38. Distivit
  39. Docemine
  40. Docibin
  41. Docivit
  42. Dodecabee
  43. Dodecavite
  44. Dodex
  45. Duodecibin
  46. Embiol
  47. Emociclina
  48. Eritrone
  49. Erycytol
  50. Erythrotin
  51. Euhaemon
  52. Extrinsic factor
  53. Factor II
  54. Fermin
  55. Fresmin
  56. Hemomin
  57. Hepagon
  58. Hepavis
  59. Hepcovite
  60. Hylugel plus
  61. Lactobacillus lactis dorner factor
  62. Macrabin
  63. Megabion
  64. Megalovel
  65. Milbedoce
  66. Millevit
  67. Nagravon
  68. Nascobal
  69. Nascobal (TN)
  70. Normocytin
  71. Novidroxin
  72. Pernaemon
  73. Pernaevit
  74. Pernipuron
  75. Plecyamin
  76. Poyamin
  77. Rebramin
  78. Redamina
  79. Redisol
  80. Rhodacryst
  81. Rubesol
  82. Rubramin
  83. Rubripca
  84. Rubrocitol
  85. Sytobex
  86. Vibalt
  87. Vibisone
  88. Virubra
  89. Vita-rubra
  90. Vitamin B12
  91. Vitamin B12 complex
  92. Vitamin B12 Preparation
  93. Vitarubin
  94. Vitral
Chemical FormulaC63H89CoN14O14P
Average Molecular Weight1356.3731
Monoisotopic Molecular Weight1355.575230332
IUPAC Name3-[(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35-bis(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-1-cyano-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2λ⁴,9,19,26,43λ⁴,44λ⁴,45λ⁴-heptaaza-15λ⁵-phospha-1-cobaltadodecacyclo[27.14.1.1¹,³⁴.1²,⁹.1¹⁰,¹³.0¹,²⁶.0³,⁸.0²³,²⁷.0²⁵,⁴².0³²,⁴⁴.0³⁹,⁴³.0³⁷,⁴⁵]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaen-40-yl]propanamide
Traditional IUPAC Name3-[(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35-bis(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-1-cyano-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2λ⁴,9,19,26,43λ⁴,44λ
CAS Registry Number68-19-9
SMILES
[C@H]1([C@H]2[C@@H](CO)O[C@@H]1N1C3=CC(=C(C)C=C3[N]([Co]345(N6C7=C(C8=[N]3C(C([C@@H]8CCC(N)=O)(C)C)=CC3=[N]4C(=C(C4=[N]5[C@@]([C@]6([C@@H]([C@@]7(C)CCC(=O)NC[C@@]([H])(C)OP(O)(=O)O2)CC(N)=O)[H])([C@@]([C@@H]4CCC(N)=O)(C)CC(N)=O)C)C)[C@@]([C@@H]3CCC(N)=O)(C)CC(N)=O)C)C#N)=C1)C)O
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassTetrapyrroles and Derivatives
Sub ClassCorrinoids
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Organic Compounds
Substituents
  • Benzimidazole
  • Carboxamide Group
  • Diterpene
  • Enamine
  • Imidazole
  • Imine
  • Lactam
  • Metallotetrapyrrole Skeleton
  • Nitrile
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Primary Carboxylic Acid Amide
  • Pyrrolidine
  • Pyrroline
  • Quaternary Ammonium Salt
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Toluene
Direct ParentCobalamin Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Antianemic Agents
  • Essential vitamins
  • Vitamins (Vitamin B Complex)
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.5 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.2 g/LALOGPS
logP0.67ALOGPS
logS-3.8ALOGPS
physiological charge0ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area500.2ChemAxon
rotatable bond count16ChemAxon
refractivity356.23ChemAxon
polarizability136.78ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • All Tissues
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Testes
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00037 (0.00009-0.00155) uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified0.00025 +/- 0.00008 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.0002385 +/- 0.0000991 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.00013 (0.00004-0.00050) uMChildren (1-13 year old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified0.00028 +/- 0.00012 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
BloodDetected and Quantified0.0003 +/- 0.0001 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified0.000016 +/- 0.0000057 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified0.000006 +/- 0.000002 umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00055 +/- 0.00041 uMAdult (>18 years old)BothHomozygous sickle cell disease
Associated Disorders and Diseases
Disease References
Homozygous sickle cell disease
  • 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
Associated OMIM IDsNone
DrugBank IDDB00115
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013264
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02823
BioCyc IDCPD-315
BiGG IDNot Available
Wikipedia LinkCyanocobalamin
NuGOwiki LinkHMDB00607
Metagene LinkHMDB00607
METLIN ID5582
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17439
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)Not Available
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. 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

Enzymes

Gene Name:
MTR
Uniprot ID:
Q99707
Gene Name:
MTHFR
Uniprot ID:
P42898
Gene Name:
MTRR
Uniprot ID:
Q9UBK8

Transporters

Gene Name:
TCN2
Uniprot ID:
P20062
Gene Name:
TCN1
Uniprot ID:
P20061
Gene Name:
GIF
Uniprot ID:
P27352
Gene Name:
CUBN
Uniprot ID:
O60494
Gene Name:
AMN
Uniprot ID:
Q9BXJ7