Adenosylcobalamin 5'-phosphate (PAMDB003485)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003485
Identification
Name: Adenosylcobalamin 5'-phosphate
Description:Adenosylcobalamin 5'-phosphate is an intermediate in the synthesis of vitamin B12. Until recently it was believed that the last reaction in the biosynthesis of coenzyme B12 was the linking of alpha-ribazole (a product of 5,6-dimethylbenzimidazole ) to adenosylcobinamide-GDP, in a reaction catalyzed by cobalamin synthase. However, it was recently shown that the true substrate for the enzyme is alpha-ribazole-5'-P, and not alpha-ribazole, and that the product of the reaction is actually adenosylcobalamin 5'-phosphate. The dephosphorylation of adenosylcobalamin 5'-phosphate by the CobC protein leads to coenzyme B12.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Adenosylcobalamin 5'-phosphoric acid
Chemical Formula: C72H101CoN18O20P2
Average Molecular Weight: 1659.5617
Monoisotopic Molecular Weight: 1658.62467598
InChI Key: ZKESCEDFYCGFMC-UHFFFAOYSA-L
InChI:InChI=1S/C62H91N13O17P2.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(83)53(41(90-57)27-89-93(84,85)86)92-94(87,88)91-31(3)26-69-49(82)18-19-59(8)37(22-46(66)79)56-62(11)61(10,25-48(68)81)36(14-17-45(65)78)51(74-62)33(5)55-60(9,24-47(67)80)34(12-15-43(63)76)38(71-55)23-42-58(6,7)35(13-16-44(64)77)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;/h20-21,23,28,31,34-37,41,52-53,56-57,83H,12-19,22,24-27H2,1-11H3,(H17,63,64,65,66,67,68,69,71,72,73,74,76,77,78,79,80,81,82,84,85,86,87,88);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2
CAS number: Not Available
IUPAC Name:??-cobalt(2+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy({[(2R)-1-({1-hydroxy-3-[(1R,2R,3R,4R,8S,13S,14S,18S,19S)-8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,??1?????1??,???tricosa-5(23),6,10(22),11,15(21),16-hexaen-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-[(phosphonooxy)methyl]oxolan-2-yl]-5,6-dimethyl-3H-1???3-benzodiazol-1-ylium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl
Traditional IUPAC Name: ??-cobalt(2+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-({hydroxy[(2R)-1-({1-hydroxy-3-[(1R,2R,3R,4R,8S,13S,14S,18S,19S)-8,13,18-tris(2-carboximidatoethyl)-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,??1?????1??,???tricosa-5(23),6,10(22),11,15(21),16-hexaen-4-yl]propylidene}amino)propan-2-yl]oxyphosphoryl}oxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-5,6-dimethyl-3H-1???3-benzodiazol-1-ylium [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl
SMILES:[Co++].[H][C@]1([CH2])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O.[H][C@@](C)(CN=C(O)CC[C@@]1(C)C2=N[C@]([H])([C@]1([H])CC(O)=N)[C@]1(C)NC(=C(C)C3=NC(=CC4=NC(=C2C)[C@@]([H])(CCC([O-])=N)C4(C)C)[C@@]([H])(CCC([O-])=N)[C@]3(C)CC(O)=N)[C@@]([H])(CCC([O-])=N)[C@]1(C)CC(O)=N)OP(O)(=O)O[C@]1([H])[C@@]([H])(COP(O)(O)=O)O[C@]([H])([N+]2=CNC3=C2C=C(C)C(C)=C3)[C@]1([H])O
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
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrolidine
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Ketimine
  • 1,2-diol
  • 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 amine
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP0.99ChemAxon
pKa (Strongest Acidic)1.11ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area526.32 Å2ChemAxon
Rotatable Bond Count29ChemAxon
Refractivity441.71 m3·mol-1ChemAxon
Polarizability137.62 Å3ChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
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
N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Adenosylcobinamide-GDP + Adenosylcobinamide-GDP > Hydrogen ion + GMP + Adenosylcobalamin 5'-phosphate
Adenosylcobalamin 5'-phosphate + Water > Phosphate + coenzyme B12
Pathways:
Spectra
Spectra:
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available