Human Metabolome Database Version 3.5

Showing metabocard for Cyanocobalamin (HMDB00607)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:50:11 -0600
HMDB ID HMDB00607
Secondary Accession Numbers
  • HMDB14263
Metabolite Identification
Common Name Cyanocobalamin
Description Cyanocobalamin (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C63H89CoN14O14P
Average Molecular Weight 1356.3731
Monoisotopic Molecular Weight 1355.575230332
IUPAC Name 3-[(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 Name 3-[(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 Number 68-19-9
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 Key SEKGMJVHSBBHRD-WZHZPDAFSA-M
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Corrinoids
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 Parent Cobalamin Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Antianemic Agents
  • Essential vitamins
  • Vitamins (Vitamin B Complex)
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point > 300 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 12.5 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 0.67 ALOGPS
LogS -3.83 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 500.2 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 356.23 ChemAxon
Polarizability 136.78 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • All Tissues
  • Kidney
  • Liver
  • Epidermis
  • Thyroid Gland
  • Brain
  • Prostate
  • Adrenal Gland
  • Adrenal Cortex
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Gonads
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00037 (0.00009-0.00155) uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
0.00025 +/- 0.00008 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.0002385 +/- 0.0000991 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.00013 (0.00004-0.00050) uM Children (1-13 year old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
0.00028 +/- 0.00012 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
0.0003 +/- 0.0001 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.000016 +/- 0.0000057 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
0.000006 +/- 0.000002 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00055 +/- 0.00041 uM Adult (>18 years old) Both Homozygous 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 Link_out
      Associated OMIM IDs None
      DrugBank ID DB00115 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB013264
      KNApSAcK ID Not Available
      Chemspider ID Not Available
      KEGG Compound ID C02823 Link_out
      BioCyc ID CPD-315 Link_out
      BiGG ID Not Available
      Wikipedia Link Cyanocobalamin Link_out
      NuGOwiki Link HMDB00607 Link_out
      Metagene Link HMDB00607 Link_out
      METLIN ID 5582 Link_out
      PubChem Compound Not Available
      PDB ID Not Available
      ChEBI ID 17439 Link_out
      References
      Synthesis Reference Gardner, 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      13. Manier JW, Beltaos E: Benign gastric ulcer in a patient with pernicious anemia. Gastroenterology. 1975 Sep;69(3):744-5. Pubmed: 1158091 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      20. Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. Pubmed: 3295013 Link_out
      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 Link_out
      22. Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. Pubmed: 11863489 Link_out
      23. Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. Pubmed: 12390080 Link_out
      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 Link_out

      Enzymes
      Name: Methionine synthase
      Reactions: Not Available
      Gene Name: MTR
      Uniprot ID: Q99707 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Methylenetetrahydrofolate reductase
      Reactions: Not Available
      Gene Name: MTHFR
      Uniprot ID: P42898 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Methylmalonyl-CoA mutase, mitochondrial
      Reactions: Not Available
      Gene Name: MUT
      Uniprot ID: P22033 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Methionine synthase reductase
      Reactions: Not Available
      Gene Name: MTRR
      Uniprot ID: Q9UBK8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial
      Reactions: Not Available
      Gene Name: MMAB
      Uniprot ID: Q96EY8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Methylmalonic aciduria type A protein, mitochondrial
      Reactions: Not Available
      Gene Name: MMAA
      Uniprot ID: Q8IVH4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Methylmalonic aciduria and homocystinuria type C protein
      Reactions: Not Available
      Gene Name: MMACHC
      Uniprot ID: Q9Y4U1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Transporters
      Name: Transcobalamin-2
      Reactions: Not Available
      Gene Name: TCN2
      Uniprot ID: P20062 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Transcobalamin-1
      Reactions: Not Available
      Gene Name: TCN1
      Uniprot ID: P20061 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Gastric intrinsic factor
      Reactions: Not Available
      Gene Name: GIF
      Uniprot ID: P27352 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cubilin
      Reactions: Not Available
      Gene Name: CUBN
      Uniprot ID: O60494 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Protein amnionless
      Reactions: Not Available
      Gene Name: AMN
      Uniprot ID: Q9BXJ7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA