Record Information
Version1.0
Creation Date2009-03-22 21:24:53 UTC
Update Date2026-05-14 16:24:00 UTC
Accession NumberCHEM000600
Identification
Common NameCyanocobalamin
ClassSmall Molecule
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. [HMDB]
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Anemic Agent
  • Cobalt Compound
  • Drug
  • Essential Vitamin
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Pollutant
  • Vitamin
  • Vitamin B Complex
Chemical Structure
Thumb
Synonyms
ValueSource
CN-CBLChEBI
CO-CYANOCOBALAMINChEBI
DicopacChEBI
Vitamin b-12ChEBI
Vitamin b12 complexChEBI
Chemical FormulaC63H88CoN14O14P
Average Molecular Mass1355.365 g/mol
Monoisotopic Mass1354.567 g/mol
CAS Registry Number68-19-9
IUPAC Namecyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-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-20-yl]cobaltylium
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)-1-cyano-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2λ⁵,9,19,26,43λ⁵,44λ⁵,45λ⁵-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)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
SMILES[C@H]1([C@@H]2[C@H]([C@@H](N3C4=CC(=C(C)C=C4[N+]([Co-3]456(N7C8=C(C9=[N+]4C(C([C@@H]9CCC(N)=O)(C)C)=CC4=[N+]5C(=C(C5=[N+]6[C@@]([C@]7([C@@H]([C@@]8(C)CCC(=O)NC[C@@]([H])(C)OP([O-])(=O)O2)CC(N)=O)[H])([C@@]([C@@H]5CCC(N)=O)(C)CC(N)=O)C)C)[C@@]([C@@H]4CCC(N)=O)(C)CC(N)=O)C)C#N)=C3)C)O1)O)CO
InChI IdentifierInChI=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;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
InChI KeyRMRCNWBMXRMIRW-WZHZPDAFSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Pterin
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Pteridine
  • Benzamide
  • Benzoic acid or derivatives
  • Aniline or substituted anilines
  • Benzoyl
  • Phenylalkylamine
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • 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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceDark red solid.
Experimental Properties
PropertyValue
Melting Point> 300°C
Boiling PointNot Available
Solubility1.25E+004 mg/L
Predicted Properties
PropertyValueSource
logP-14ChemAxon
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-0.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area440.79 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity344.12 m³·mol⁻¹ChemAxon
Polarizability134.61 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, Positivesplash10-08g0-0029000000-77072081600b65a1c4d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029l-0039000000-38d31a7c52468bf044e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0090000000-932c5dd7c708f3803c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2i-0029000000-79a52bb6630feb8682a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-2098000000-8f39892e9be557c444a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9043000000-9ef3360537c06103842fSpectrum
Toxicity Profile
Route of ExposureInhalation (26) ; oral (26) ; dermal (26) Readily absorbed in the lower half of the ileum.
Mechanism of ToxicityVitamin B12 is used in the body in two forms: Methylcobalamin and 5-deoxyadenosyl cobalamin. The enzyme methionine synthase needs methylcobalamin as a cofactor. This enzyme is involved in the conversion of the amino acid homocysteine into methionine. Methionine in turn is required for DNA methylation. 5-Deoxyadenosyl cobalamin is a cofactor needed by the enzyme that converts L-methylmalonyl-CoA to succinyl-CoA. This conversion is an important step in the extraction of energy from proteins and fats. Furthermore, succinyl CoA is necessary for the production of hemoglobin, the substances that carries oxygen in red blood cells.
MetabolismCobalt is absorbed though the lungs, gastrointestinal tract, and skin. Since it is a component of the vitamin B12 (cyanocobalamin), it is distributed to most tissues of the body. It is transported in the blood, often bound to albumin, with the highest levels being found in the liver and kidney. Cobalt is excreted mainly in the urine and faeces. (26) Half Life: Approximately 6 days (400 days in the liver).
Toxicity ValuesORL-MUS LD50 > 8000 mg/kg
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (29)
Uses/SourcesCyanocobalamin is a form of vitamin B12. (30) It is used for treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
Minimum Risk LevelChronic Inhalation: 0.0001 mg/m3 (28) Intermediate Oral: 0.01 mg/kg/day (28)
Health EffectsExposure to high amount of cobalt can cause heart, lung, kidney, and liver damage. Skin contact is known to result in contact dermatitis. Cobalt may also have mutagenic and carcinogenic effects. (26, 27)
SymptomsAnaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. Cobalt inhalation can cause asthma-like breathing problems. Skin contact is known to result in contact dermatitis, which is characterized by irritation and rashes. Ingesting large amounts of cobalt may cause nausea and vomiting. (31)
TreatmentTreatment of cobalt poisoning is symptomatic. (26)
Concentrations
Not Available
DrugBank IDDB00115
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001534
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyanocobalamin
Chemspider IDNot Available
ChEBI ID17439
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Robert H. Allen, “Preparation of samples for vitamin B12 and/or folate assay and assay.” U.S. Patent US4451571, issued October, 1982.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=29286160