Record Information
Version2.0
Creation Date2012-05-31 13:55:35 -0600
Update Date2015-10-23 17:32:54 -0600
Secondary Accession Numbers
  • ECMDB02086
Identification
Name:Adenosylcobalamin
DescriptionAdenosylcobalamin 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
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
Weight:Average: 1580.5897
Monoisotopic: 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[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]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[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]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
ClassificationNot classified
Physical Properties
State:Solid
Charge:3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity392.44 m³·mol⁻¹ChemAxon
Polarizability160.65 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:Not Available
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

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 ATP binding
Specific function:
Required for both de novo synthesis of the corrin ring for the assimilation of exogenous corrinoids. Participates in the adenosylation of a variety of incomplete and complete corrinoids
Gene Name:
btuR
Uniprot ID:
P0A9H5
Molecular weight:
21999
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.
General function:
Involved in cobalamin 5'-phosphate synthase activity
Specific function:
Joins Ado-cobinamide-GDP and alpha-ribazole to generate adenosylcobalamin (Ado-cobalamin)
Gene Name:
cobS
Uniprot ID:
P36561
Molecular weight:
26385
Reactions
GDP-cobinamide + alpha-ribazole = cobalamin + GMP.
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
Uniprot ID:
P52086
Molecular weight:
23308
Reactions
Adenosylcobalamin 5'-phosphate + H(2)O = coenzyme B12 + phosphate.
Alpha-ribazole 5'-phosphate + H(2)O = alpha-ribazole + phosphate.
General function:
Involved in ATP binding
Specific function:
Converts CNB12 to ADOB12
Gene Name:
eutT
Uniprot ID:
P65643
Molecular weight:
30171
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.
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 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
General function:
Involved in protein transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates. Protects exbD from proteolytic degradation and functionally stabilizes tonB
Gene Name:
exbB
Uniprot ID:
P0ABU7
Molecular weight:
26287
General function:
Involved in transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates
Gene Name:
exbD
Uniprot ID:
P0ABV2
Molecular weight:
15527
General function:
Involved in iron ion transmembrane transporter activity
Specific function:
Interacts with outer membrane receptor proteins that carry out high-affinity binding and energy dependent uptake into the periplasmic space of specific substrates such as cobalamin, and various iron compounds (such as iron dicitrate, enterochelin, aerobactin, etc.). In the absence of tonB these receptors bind their substrates but do not carry out active transport. TonB also interacts with some colicins and is involved in the energy- dependent, irreversible steps of bacteriophages phi 80 and T1 infection. It could act to transduce energy from the cytoplasmic membrane to specific energy-requiring processes in the outer membrane, resulting in the release into the periplasm of ligands bound by these outer membrane proteins
Gene Name:
tonB
Uniprot ID:
P02929
Molecular weight:
26094