Cyanocobalamin (YMDB01525)

Identification
YMDB IDYMDB01525
NameCyanocobalamin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCyanocobalamin 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • alpha-(5,6-dimethylbenzimidazolyl)cobamide
  • Anacobin
  • Berubigen
  • Betaline-12
  • Betolvex
  • Bevidox
  • Bevidox concentrate
  • Biocobalamine
  • Byladoce
  • Cabadon m
  • Cbl
  • Cob(III)alamin
  • Cobadoce forte
  • Cobalamin (III)
  • cobalamin(1+)
  • cobalamin(III)
  • Cobalin
  • Cobavite
  • Covit
  • Crystamin
  • Crystamine
  • Crystimin
  • Crystwel
  • Cyano-B12
  • Cyanobalamin concentrate
  • Cyanocob(III)alamin
  • Cyanocobalamine
  • Cycobemin
  • Cycolamin
  • Cykobemin
  • Cykobeminet
  • Cyredin
  • Cytacon
  • Cytamen
  • Cytobion
  • Depinar
  • Dicopac
  • Dimethylbenzimidazoylcobamide
  • Distivit
  • Docemine
  • Docibin
  • Docivit
  • Dodecabee
  • Dodecavite
  • Dodex
  • Duodecibin
  • Embiol
  • Emociclina
  • Eritrone
  • Erycytol
  • Erythrotin
  • Euhaemon
  • Extrinsic factor
  • Factor II
  • Fermin
  • Fresmin
  • Hemomin
  • Hepagon
  • Hepavis
  • Hepcovite
  • Macrabin
  • Megabion
  • Megalovel
  • Milbedoce
  • Millevit
  • Nagravon
  • Normocytin
  • Novidroxin
  • Pernaemon
  • Pernaevit
  • Pernipuron
  • Plecyamin
  • Poyamin
  • Rebramin
  • Redamina
  • Redisol
  • Rhodacryst
  • Rubesol
  • Rubripca
  • Rubrocitol
  • Vibalt
  • Vibisone
  • Virubra
  • Vita-rubra
  • Vitamin B12
  • Vitamin B12 complex
  • Vitamin B12 Preparation
  • Vitamine B12
  • Vitarubin
  • Vitral
CAS number68-19-9
WeightAverage: 1355.3652
Monoisotopic: 1354.5674053
InChI KeyAPJNTFOUCQSOLK-RKRHPEFLSA-M
InChIInChI=1S/C62H89N13O14P.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,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);;/q-1;;+2/p-1/b54-32-;;/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;;/m1../s1
IUPAC NameNot Available
Traditional IUPAC NameNot Available
Chemical FormulaC63H88CoN14O14P
SMILES[C@@H]1(C2N3C4=C(C5=[N]6C(C([C@@H]5CCC(N)=O)(C)C)=CC5=[N]7C(=C(C8=[N]([C@@]2([C@@]([C@@H]8CCC(N)=O)(C)CC(N)=O)C)[Co+]367([N]2=CN(C3=C2C=C(C(C)=C3)C)[C@H]2O[C@H](CO)[C@@H](OP([O-])(=O)O[C@H](C)CNC(=O)CC[C@]14C)[C@H]2O)C#N)C)[C@@]([C@@H]5CCC(N)=O)(C)CC(N)=O)C)CC(N)=O
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
  • Pentose phosphate
  • Benzimidazole
  • Fatty acyl
  • Benzenoid
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Fatty amide
  • Tetrahydrofuran
  • Pyrroline
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Transition metal cyanide salt
  • Organic metal salt
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Metalloheterocycle
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic cobalt salt
  • Organic salt
  • Organic zwitterion
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organometallic compound
  • Organic transition metal moeity
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point>300 °C
Experimental Properties
PropertyValueReference
Water Solubility12.5 mg/mL [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP0.85ALOGPS
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area503.03 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity355.11 m³·mol⁻¹ChemAxon
Polarizability136.25 ųChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.0 ± 0.0 µM hops, malted barleyanaerobicBrewer's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
SpectraNot Available
References
References:
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
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.
External Links:
ResourceLink
CHEBI ID28911
HMDB IDHMDB00607
Pubchem Compound ID5462245
Kegg IDC05776
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDCyanocobalamin
BioCyc IDCPD-315