Record Information
Version1.0
Creation date2010-04-08 22:10:37 UTC
Update date2019-11-26 03:08:13 UTC
Primary IDFDB013264
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanocobalamin
DescriptionAntipernicious anaemia factor isolated from liver extracts; now obtained comly. from fermentation liquors of Streptomyces griseus and other microorganisms, e.g. Propionibacterium shermanii, Pseudomonas denitrificans. Nutrient, dietary supplement, stabiliser. Haematopoietic vitamin [DFC] Cyanocobalamin is an especially common vitamer of the vitamin B12 family. B12'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). B12 cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of B12 are bacteria and archaea. Higher plants do not concentrate vitamin B12 from the soil and so are a poor source of the substance as compared with animal tissues. Vitamin B12 is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products. [Wikipedia]
CAS Number68-19-9
Structure
Thumb
Synonyms
SynonymSource
a-(5,6-Dimethylbenzimidazoyl)cobamide cyanidedb_source
AlphamineMetaCyc
Anacobinbiospider
Athletebiospider
Athlete GSbiospider
B-12 Dots 500mcgbiospider
B12 1000mcg (Methylcobalamin)biospider
B12 250mcg Cyanocobalaminbiospider
Berubigenbiospider
Betalin 12 Crystallinebiospider
Betaline-12biospider
Betolvexbiospider
Bevidoxbiospider
Bevidox concentratebiospider
Biocobalaminebiospider
Byladocebiospider
Cabadon mbiospider
Cobadoce fortebiospider
Cobalinbiospider
Cobamindb_source
Cobavitebiospider
Copharvit 5000biospider
Covitbiospider
Crystaminbiospider
Crystaminebiospider
Crystiminbiospider
Crystwelbiospider
Cyano-B12biospider
Cyanobalamin concentratebiospider
Cyanocob(III)alaminbiospider
Cyanocobalaminbiospider
Cyanocobalamin (JP15/USP)biospider
Cyanocobalamin (JP15/USP/INN)biospider
Cyanocobalamin, BAN, INN, USANdb_source
Cyanocobalaminebiospider
Cyanocobalminbiospider
CyanojectMetaCyc
Cycobeminbiospider
Cycolaminbiospider
Cykobemindb_source
Cykobeminetbiospider
Cyominbiospider
Cyomin (TN)biospider
Cyredinbiospider
Cytaconbiospider
Cytamenbiospider
Cytobionbiospider
Depinarbiospider
Dicopacbiospider
Dimethylbenzimidazoylcobamidebiospider
Distivitbiospider
Doceminebiospider
Docibinbiospider
Docivitbiospider
Dodecabeebiospider
Dodecavitebiospider
Dodexbiospider
Duodecibinbiospider
Embiolbiospider
Emociclinabiospider
Eritronebiospider
Erycytolbiospider
Erythrotinbiospider
Euhaemonbiospider
Extrinsic factorbiospider
Factor IIdb_source
Ferminbiospider
Formula #1 - Cap 3mcgbiospider
Fresminbiospider
Hemominbiospider
Hepagonbiospider
Hepavisbiospider
Hepcovitebiospider
HydrobexanMetaCyc
Hylugel plusbiospider
Lactobacillus lactis dorner factorbiospider
Liquid Vitamin B12biospider
Macrabinbiospider
Mega B12 Pwr 1mg/Gmbiospider
Megabionbiospider
Megalovelbiospider
Milbedocebiospider
Millevitbiospider
Nagravonbiospider
Nascobalbiospider
Nascobal (TN)biospider
Normocytinbiospider
Novidroxinbiospider
Pernaemonbiospider
Pernaevitbiospider
Pernipuronbiospider
Plecyaminbiospider
Poyaminbiospider
Primebiospider
Rebraminbiospider
Redaminabiospider
Redisolbiospider
Rhodacrystbiospider
Rubesolbiospider
Rubraminbiospider
Rubramin PCbiospider
Rubramin PC (TN)biospider
Rubripcabiospider
Rubrocitolbiospider
Sytobexbiospider
Vibaltbiospider
Vibisonebiospider
Virubrabiospider
Vita-rubrabiospider
Vitamin B12 100 Mcgbiospider
Vitamin B12 1000 Mcgbiospider
Vitamin B12 1000mcg Nuggetsbiospider
Vitamin B12 100mcgbiospider
Vitamin B12 250mcgbiospider
Vitamin B12 500mcgbiospider
Vitamin B12 Complexbiospider
Vitamin B12 Preparationbiospider
Vitarubinbiospider
Vitralbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP2.68ALOGPS
logP1.11ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area479.79 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity430.84 m³·mol⁻¹ChemAxon
Polarizability134.49 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC63H88CoN14O14P
IUPAC namelambda2-cobalt(2+) ion 1-(3-hydroxy-4-{[hydroxy({1-[(1-hydroxy-3-{8,13,18-tris[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-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-4-yl}propylidene)amino]propan-2-yl}oxy)phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl)-5,6-dimethyl-3H-1lambda5,3-benzodiazol-1-ylium cyano
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
InChI KeyRMRCNWBMXRMIRW-UHFFFAOYSA-L
Isomeric SMILESC12N3C4=CC(=C(C)C=C4[N]([Co+]456(N7C8=C(C9=[N]4C(C(C9(C)CC(N)=O)CCC(N)=O)=CC4=[N]5C(C(C4(C)C)CCC(N)=O)=C(C4=[N]6C(C(C4(C)CCC(=O)NCC(C)OP([O-])(=O)OC(C1O)C(CO)O2)CC(N)=O)C7(C(C8CCC(N)=O)(C)CC(N)=O)C)C)C)C#N)=C3)C
Average Molecular Weight1355.3652
Monoisotopic Molecular Weight1354.5674053
Classification
DescriptionThis compound 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
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Benzimidazole
  • Dialkyl phosphate
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrolidine
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Ketimine
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Enamine
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organic cobalt salt
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Foods
  • Dairy products
  • Eggs
  • Meats
  • Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 55.83%; H 6.54%; Co 4.35%; N 14.47%; O 16.53%; P 2.29%DFC
    Melting PointMp 210-220 darkens°DFC
    Boiling PointNot Available
    Experimental Water Solubility12.5 mg/mLMERCK INDEX (1996)
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data550 () (no solvent reported)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    SpectraNot Available
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDC02823
    Pubchem Compound ID5462245
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDDB00115
    HMDB IDHMDB00607
    CRC / DFC (Dictionary of Food Compounds) IDHQL41-U:HQL41-U
    EAFUS ID3858
    Dr. Duke IDCYANOCOBALAMIN|VIT-B12
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDCyanocobalamin
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    Methylmalonyl-CoA mutase, mitochondrialMUTP22033
    Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrialMMABQ96EY8
    Methylmalonic aciduria type A protein, mitochondrialMMAAQ8IVH4
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).