Adenosylcobalamin (PAMDB000439)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000439
Identification
Name: Adenosylcobalamin
Description:Adenosylcobalamin is one of two metabolically active forms of vitamin B12. it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. (E.C. 5.4.99.2).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (5'-Deoxy-5'-adenosyl)cobamide coenzyme
  • (5,6-dimethylbenzimidazolyl)cobamide coenzyme
  • 5'-Deoxy-5'-adenosyl vitamin B12
  • 5'-Deoxy-5'-adenosylcobalamin
  • 5'-Deoxyadenosyl vitamin B12
  • 5'-Deoxyadenosyl-5,6-dimethylbenzimidazolylcobamide
  • 5'-Deoxyadenosylcobalamin
  • 5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide
  • 5,6-Dimethylbenzimidazolyl-Co-5'-deoxyadenosylcobamide
  • Adenosylcobalamin
  • Adenosylcobalamin 5'-phosphate
  • Adenosylcobalamin 5'-phosphoric acid
  • Calomide
  • CoB12
  • Cobalamin coenzyme
  • Cobamamid
  • Cobamamide
  • Cobamamide 5'-phosphate
  • Cobamamide 5'-phosphoric acid
  • Cobamide coenzyme
  • Coenzyme B12
  • Deoxyadenosylcobalamin
  • Dibencozide
  • Funacomide
  • Vitamin B12
  • Vitamin B12 coenzyme
  • Vitamin B12 coenzymes
  • Vitamin B12
Chemical Formula: C72H101CoN18O17P
Average Molecular Weight: 1580.5897
Monoisotopic Molecular Weight: 1579.666170602
InChI Key: ZIHHMGTYZOSFRC-QRVZQHAISA-M
InChI:InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1
CAS number: 13870-90-1
IUPAC Name:{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,??1?????1??,???tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
Traditional IUPAC Name: {[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,??1?????1??,???tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
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(N)=O)C2N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)\[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)/C(C)(C)[C@@H]1CCC(N)=O)N1C=NC2=C1C=C(C)C(C)=C2
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Tetrapyrroles and derivatives
Sub ClassCorrinoids
Direct Parent Cobalamin derivatives
Alternative Parents
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • 1-ribofuranosylbenzimidazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Aminopyrimidine
  • Fatty acyl
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrolidine
  • Oxolane
  • Imidazole
  • Azole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketimine
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organic metal salt
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organic cobalt salt
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organometallic compound
  • Organic transition metal moeity
  • Imine
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0256 mg/mLALOGPS
logP2.1ALOGPS
logP-5.9ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area570.54 Å2ChemAxon
Rotatable Bond Count30ChemAxon
Refractivity392.44 m3·mol-1ChemAxon
Polarizability160.65 Å3ChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Water + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Adenosylcobalamin > Adenosylcobalamin + ADP + Hydrogen ion + Phosphate
Adenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + Triphosphate
Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole > Adenosylcobalamin + Guanosine monophosphate + Hydrogen ion
Adenosine triphosphate + Cob(I)alamin <> Triphosphate + Adenosylcobalamin
Adenosylcobalamin + Guanosine monophosphate <> Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole
adenosylcobalamin 5'-phosphate + Water > Adenosylcobalamin + Phosphate
Adenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphate
Adenosylcobalamin + Water > Adenosylcobalamin + Inorganic phosphate
Adenosylcobinamide-GDP + N1-(alpha-D-ribosyl)-5,6-dimethyl-benzimidazole + N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole <> Guanosine monophosphate + Adenosylcobalamin + Adenosylcobalamin 5'-phosphate
Pathways:
Spectra
Spectra:
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18408
HMDB IDHMDB02086
Pubchem Compound ID6436143
Kegg IDC00194
ChemSpider IDNot Available
WikipediaAdenosylcobalamin
BioCyc IDADENOSYLCOBALAMIN
EcoCyc IDADENOSYLCOBALAMIN

Enzymes

Protein Details
• Alpha-ribazole phosphatase
General function:
Involved in catalytic activity
Specific function:
Converts N1-(5-phospho-alpha-D-ribosyl)-5,6- dimethylbenzimidazole into N1-alpha-D-ribosyl-5,6- dimethylbenzimidazole; involved in the assembly of the nucleotide loop of cobalamin
Gene Name:
cobC
Locus Tag:
PA1276
Molecular weight:
36.7 kDa
Reactions
Adenosylcobalamin 5'-phosphate + H(2)O = coenzyme B12 + phosphate.
Alpha-ribazole 5'-phosphate + H(2)O = alpha-ribazole + phosphate.

Transporters