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Record Information
Version3.6
Creation Date2008-08-15 14:47:48 UTC
Update Date2017-03-02 21:28:22 UTC
HMDB IDHMDB06903
Secondary Accession Numbers
  • HMDB06964
Metabolite Identification
Common NameAdenosyl cobinamide
DescriptionAdenosyl cobinamide is an intermediate in vitamin B12 cofactor biosynthesis and adenosylcobalamin synthesis. It is a substrate for the enzyme Cob(I)yrinic acid a,c-diamide adenosyltransferase which is found in the mitochondria. The enzyme is responsible for the following 2 step reaction: ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide and then ATP + cobinamide = triphosphate + adenosylcobinamide.
Structure
Thumb
Synonyms
ValueSource
5'-Deoxy-5'-adenosylcobinamideHMDB
AdenosylcobinamideHMDB
Chemical FormulaC58H84CoN16O11
Average Molecular Weight1240.3214
Monoisotopic Molecular Weight1239.583747804
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)-18-(2-{[(2R)-2-hydroxypropyl]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]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)-18-(2-{[(2R)-2-hydroxypropyl]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]cobaltbis(ylium)
CAS Registry NumberNot Available
SMILES
C[C@@H](O)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
InChI Identifier
InChI=1S/C48H73N11O8.C10H12N5O3.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)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;/h19,23,26-29,43,60H,10-18,20-22H2,1-9H3,(H14,49,50,51,52,53,54,55,56,57,58,59,61,62,63,64,65,66,67);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 KeyPAUPKJHCFVPREX-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
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Fatty acyl
  • Fatty amide
  • Oxolane
  • Azole
  • Imidazole
  • Pyrrolidine
  • Pyrroline
  • Heteroaromatic compound
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Ketimine
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic transition metal salt
  • Oxacycle
  • Azacycle
  • Organic metal salt
  • Organic nitrogen compound
  • Alcohol
  • Organic transition metal moeity
  • Organometallic compound
  • Organonitrogen compound
  • Imine
  • Organooxygen compound
  • Primary amine
  • Organic salt
  • Organic cobalt salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Transition metal alkyl
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.019 mg/mLALOGPS
logP2.12ALOGPS
logP-5.2ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area467.5 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity313.7 m3·mol-1ChemAxon
Polarizability126.05 Å3ChemAxon
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
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 IDFDB024150
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06508
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06903
Metagene LinkHMDB06903
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID2480
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
Reactions
Adenosine triphosphate + Cobinamide → Triphosphate + Adenosyl cobinamidedetails
Adenosine triphosphate + Cobinamide → PPPi + Adenosyl cobinamidedetails