Cyanocobalamin (ECMDB21386) (M2MDB001781)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)Transporters (6)XML
Proteins (6)
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
DescriptionB12 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
MOLSDFPDBSMILESInChI
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:cyanocobalamin
Traditional IUPAC Name:cyanocobalamin
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
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
  • 1-ribofuranosylbenzimidazole
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Monosaccharide
  • Fatty acyl
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Fatty amide
  • Phosphoric acid ester
  • Benzenoid
  • Alkyl phosphate
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Pyrrolidine
  • Pyrroline
  • Tetrahydrofuran
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketimine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Organic metal salt
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Transition metal cyanide salt
  • Organic transition metal salt
  • Organic salt
  • Hydrocarbon derivative
  • Organic transition metal moeity
  • Imine
  • Organometallic compound
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
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 Solubility0.038 g/LALOGPS
logP1.87ALOGPS
logS-4.5ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)13.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area487.61 ŲChemAxon
Polarizability137.36 ųChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cyanocobalamin + Adenosine triphosphate + Water + Cyanocobalamin > Adenosine diphosphate + Phosphate + Hydrogen ion + Cyanocobalamin + ADP
SMPDB Pathways:
adenosylcobalamin salvage from cobinamidePW001884 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2505000009-edb77b0741ab131f8e9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2903000005-7209eb5b1abfc27349e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2920000004-63934a026bb66dd6d2f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-4319000001-284fb8fc72f8ccc63196View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0912000001-6cad42b357edecf06495View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-7900000000-d146eb8a599bacc80954View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-0fc6a488f1be9c417828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmi-2097000000-ff8aea846c78c61c8849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007a-9500000000-229e183ee286be69cc43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052s-0019000002-5c7fd3769fbb6bde0dd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-1097000000-a17c21bdb2ecc6da8610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01em-4890000011-4fe6c6d7508c45900ce6View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 IDNot Available
WikipediaCyanocobalamin
BioCyc IDCPD-315
EcoCyc IDCPD-315

Enzymes

Protein Details
1. Vitamin B12 import ATP-binding protein BtuD
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).
Protein Details
2. Vitamin B12 import system permease protein BtuC
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
Protein Details
3. Vitamin B12-binding protein
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

Protein Details
1. Vitamin B12 import ATP-binding protein BtuD
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).
Protein Details
2. Vitamin B12 import system permease protein BtuC
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
Protein Details
3. Vitamin B12 import system permease protein BtuC
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
Protein Details
4. Vitamin B12 transporter BtuB
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
Protein Details
5. Vitamin B12 import system permease protein BtuC
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
Protein Details
6. Vitamin B12-binding protein
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