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Showing metabocard for Propinol adenylate (HMDB06806)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version3.6
Creation Date2008-08-12 13:30:00 UTC
Update Date2017-03-02 21:28:19 UTC
HMDB IDHMDB06806
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropinol adenylate
DescriptionPropinol adenylate is involved in the propanoate metabolism pathway. Propinol adenylate can be reversibly produced from propanoate or propanoyl-CoA by acetyl-CoA synthetase [EC:6.2.1.1] and propionyl-CoA synthetase [EC:6.2.1.17].
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5'-Adenylic acid propanoic acid anhydrideChEBI
5'-Adenylic acid propionic acid anhydrideChEBI
5'-O-[Hydroxy(propionyloxy)phosphoryl]adenosineChEBI
Propanoyl-adenosine monophosphateChEBI
Propionyl-adenosine monophosphateChEBI
Propionyl-AMPChEBI
PropionyladenylateChEBI
5'-Adenylate propanoate anhydrideGenerator
Propinol adenylic acidGenerator
5'-Adenylate propionate anhydrideGenerator
Propanoyl-adenosine monophosphoric acidGenerator
Propionyl-adenosine monophosphoric acidGenerator
Propionyladenylic acidGenerator
Chemical FormulaC13H18N5O8P
Average Molecular Weight403.2845
Monoisotopic Molecular Weight403.089299089
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(propanoyloxy)phosphinic acid
Traditional Namepropionyl-AMP
CAS Registry NumberNot Available
SMILES
CCC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C13H18N5O8P/c1-2-7(19)26-27(22,23)24-3-6-9(20)10(21)13(25-6)18-5-17-8-11(14)15-4-16-12(8)18/h4-6,9-10,13,20-21H,2-3H2,1H3,(H,22,23)(H2,14,15,16)/t6-,9-,10-,13-/m1/s1
InChI KeyZGNGGJLVZZHLQM-ZRFIDHNTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent5'-acylphosphoadenosines
Alternative Parents
Substituents
  • 5'-acylphosphoadenosine
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Acyl phosphate
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidine
  • Imidolactam
  • Primary aromatic amine
  • Phosphoric acid ester
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Amino acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility2.99 mg/mLALOGPS
logP-2ALOGPS
logP-4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area192.14 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.85 m3·mol-1ChemAxon
Polarizability35.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Malonic AciduriaSMP00198Not Available
Malonyl-coa decarboxylase deficiencySMP00502Not Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersSMP00201Not Available
Propanoate MetabolismSMP00016map00640
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 IDFDB024092
KNApSAcK IDNot Available
Chemspider ID389700
KEGG Compound IDC05983
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06806
Metagene LinkHMDB06806
METLIN IDNot Available
PubChem Compound440863
PDB IDNot Available
ChEBI ID62415
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Acetyl-coenzyme A synthetase, cytoplasmic
General function:
Involved in acetate-CoA ligase activity
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:
ACSS2
Uniprot ID:
Q9NR19
Molecular weight:
78579.11
Reactions
Propinol adenylate + Coenzyme A → Adenosine monophosphate + Propionyl-CoAdetails
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails
Enzyme Details
2. Acetyl-coenzyme A synthetase 2-like, mitochondrial
General function:
Involved in acetate-CoA ligase activity
Specific function:
Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Molecular weight:
74625.88
Reactions
Propinol adenylate + Coenzyme A → Adenosine monophosphate + Propionyl-CoAdetails
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails
Enzyme Details
3. ACSS2 protein
General function:
Involved in acetate-CoA ligase activity
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Molecular weight:
59346.4
Enzyme Details
4. Acyl-CoA synthetase short-chain family member 3, mitochondrial
General function:
Not Available
Specific function:
Activates acetate so that it can be used for lipid synthesis or for energy generation (By similarity).
Gene Name:
ACSS3
Uniprot ID:
Q9H6R3
Molecular weight:
74777.655
Reactions
Propinol adenylate + Coenzyme A → Adenosine monophosphate + Propionyl-CoAdetails
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylatedetails