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Record Information
Version4.0
Creation Date2009-04-06 16:20:38 UTC
Update Date2017-09-27 08:26:54 UTC
HMDB IDHMDB0012184
Secondary Accession Numbers
  • HMDB12184
Metabolite Identification
Common NameAdenosyl cobinamide phosphate
DescriptionAdenosyl cobinamide phosphate, a known intermediate of the de novo biosynthetic pathway, is involved in Porphyrin and chlorophyll metabolism.In Salmonella typhimurium LT2, under anaerobic conditions, CobU (EC 2.7.7.62 and EC 2.7.1.156), CobT (EC 2.4.2.21), CobC (EC 3.1.3.73) and CobS (EC 2.7.8.26) catalyse reactions in the nucleotide loop. assembly pathway, which convert adenosylcobinamide (AdoCbi) into. adenosylcobalamin (AdoCbl). CobT and CobC are involved in 5,6-dimethylbenzimidazole activation whereby. 5,6-dimethylbenzimidazole is converted to its riboside,. alpha-ribazole. The second branch of the nuclotide loop assembly. pathway is the cobinamide (Cbi) activation branch where AdoCbi or. adenosylcobinamide-phosphate is converted to the activated. intermediate AdoCbi-GDP by the bifunctional enzyme Cob U. The final. step in adenosylcobalamin biosynthesis is the condensation of. AdoCbi-GDP with alpha-ribazole, which is catalysed by EC 2.7.8.26,. cobalamin synthase (CobS), to yield adenosylcobalamin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC58H85CoN16O14P
Average Molecular Weight1320.3013
Monoisotopic Molecular Weight1319.550078214
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-2,3,6,8,13,13,16,18-octamethyl-18-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-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]cobaltbis(ylium)
Traditional Name{[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-2,3,6,8,13,13,16,18-octamethyl-18-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-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]cobaltbis(ylium)
CAS Registry NumberNot Available
SMILES
C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++]CC3OC(C(O)C3O)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(=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)OP(O)(O)=O
InChI Identifier
InChI=1S/C48H74N11O11P.C10H12N5O3.Co/c1-23(70-71(67,68)69)22-55-38(66)16-17-45(6)29(18-35(52)63)43-48(9)47(8,21-37(54)65)28(12-15-34(51)62)40(59-48)25(3)42-46(7,20-36(53)64)26(10-13-32(49)60)30(56-42)19-31-44(4,5)27(11-14-33(50)61)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43H,10-18,20-22H2,1-9H3,(H16,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;;/m1../s1
InChI KeyQYLVQAVCDRLDAQ-VUCSARQQSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Fatty amide
  • Phosphoric acid ester
  • Fatty acyl
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Alkyl phosphate
  • Monosaccharide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Pyrrolidine
  • Pyrroline
  • Secondary alcohol
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • 1,2-diol
  • Carboxamide group
  • Ketimine
  • Organic transition metal salt
  • Carboxylic acid derivative
  • Organic metal salt
  • Azacycle
  • Oxacycle
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Organic transition metal moeity
  • Imine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Transition metal alkyl
  • Organopnictogen compound
  • Organometallic compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic cobalt salt
  • Amine
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP1.69ALOGPS
logP-7.5ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.52ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area514.03 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity324.57 m³·mol⁻¹ChemAxon
Polarizability130.27 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028837
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06509
BioCyc IDADENOSYLCOBINAMIDE-P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID2481
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available