Record Information
Version2.0
Creation Date2012-07-30 14:55:41 -0600
Update Date2015-09-17 15:41:05 -0600
Secondary Accession Numbers
  • ECMDB21386
Identification
Name:Cyanocobalamin
Description:B12 is the most chemically complex of all the vitamins. 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). Vitamin 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 B 12 from the soil and so are a poor source of the substance as compared with animal tissues.
Structure
Thumb
Synonyms:
  • Alphamine
  • Anacobin
  • Berubigen
  • Betalin 12 Crystalline
  • Betaline-12
  • Betolvex
  • Bevidox
  • Bevidox concentrate
  • Bevidox concentric acid
  • Biocobalamine
  • Byladoce
  • Cabadon m
  • Cobadoce forte
  • Cobalin
  • Cobavite
  • Copharvit 5000
  • Covit
  • Crystamin
  • Crystamine
  • Crystimin
  • Crystwel
  • Cyano-B12
  • Cyanobalamin concentrate
  • Cyanobalamin concentric acid
  • Cyanocob(III)alamin
  • Cyanocobalamin
  • Cyanocobalamin (JP15/USP)
  • Cyanocobalamine
  • Cyanocobalmin
  • Cyanoject
  • Cycobemin
  • Cycolamin
  • Cykobemin
  • Cykobeminet
  • Cyomin
  • 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
  • Hydrobexan
  • Hylugel plus
  • Lactobacillus lactis dorner factor
  • Macrabin
  • Megabion
  • Megalovel
  • Milbedoce
  • Millevit
  • Nagravon
  • Nascobal
  • Nascobal (TN)
  • Normocytin
  • Novidroxin
  • Pernaemon
  • Pernaevit
  • Pernipuron
  • Plecyamin
  • Poyamin
  • Rebramin
  • Redamina
  • Redisol
  • Rhodacryst
  • Rubesol
  • Rubramin
  • Rubripca
  • Rubrocitol
  • Sytobex
  • Vibalt
  • Vibisone
  • Virubra
  • Vita-rubra
  • Vitamin B12
  • Vitamin B12 Preparation
  • Vitarubin
  • Vitral
Chemical Formula:C63H89CoN14O14P
Weight:Average: 1356.3731
Monoisotopic: 1355.575230332
InChI Key:SEKGMJVHSBBHRD-WZHZPDAFSA-M
InChI: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
CAS number:68-19-9
IUPAC Name:Not Available
Traditional IUPAC Name:Not Available
SMILES:OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@]([H])(C)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co]C#N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)N1C=NC2=CC(C)=C(C)C=C12
Chemical Taxonomy
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
Physical Properties
State:Solid
Charge:0
Melting point:>300 °C
Experimental Properties:
PropertyValueSource
Water Solubility:12.5 mg/mL [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0424 mg/mLALOGPS
logP0.84ALOGPS
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area503.03 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity355.41 m3·mol-1ChemAxon
Polarizability135.85 Å3ChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
adenosylcobalamin salvage from cobinamidePW001884 Pw001884Pw001884 greyscalePw001884 simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID28911
HMDB IDHMDB00607
Pubchem Compound ID5462245
Kegg IDC02823
ChemSpider ID10619269
WikipediaCyanocobalamin
BioCyc IDCPD-315
EcoCyc IDCPD-315

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Responsible for energy coupling to the transport system
Gene Name:
btuD
Uniprot ID:
P06611
Molecular weight:
27081
Reactions
ATP + H(2)O + vitamin B12(Out) = ADP + phosphate + vitamin B12(In).
General function:
Involved in cobalamin transport
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
Gene Name:
btuC
Uniprot ID:
P06609
Molecular weight:
34949
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Binds vitamin B12 and delivers it to the periplasmic surface of BtuC
Gene Name:
btuF
Uniprot ID:
P37028
Molecular weight:
29367

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Responsible for energy coupling to the transport system
Gene Name:
btuD
Uniprot ID:
P06611
Molecular weight:
27081
Reactions
ATP + H(2)O + vitamin B12(Out) = ADP + phosphate + vitamin B12(In).
General function:
Involved in cobalamin transport
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
Gene Name:
btuC
Uniprot ID:
B1XG18
Molecular weight:
34949
General function:
Involved in cobalamin transport
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
Gene Name:
btuC
Uniprot ID:
C4ZYH3
Molecular weight:
34949
General function:
Involved in receptor activity
Specific function:
Involved in the active translocation of vitamin B12 (cyanocobalamin) across the outer membrane to the periplasmic space. It derives its energy for transport by interacting with the trans-periplasmic membrane protein tonB. Is also a receptor for bacteriophages BF23 and C1, and for A and E colicins
Gene Name:
btuB
Uniprot ID:
P06129
Molecular weight:
68407
General function:
Involved in cobalamin transport
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
Gene Name:
btuC
Uniprot ID:
P06609
Molecular weight:
34949
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Binds vitamin B12 and delivers it to the periplasmic surface of BtuC
Gene Name:
btuF
Uniprot ID:
P37028
Molecular weight:
29367