You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2008-08-12 13:30:00 UTC
Update Date2017-10-23 19:04:24 UTC
HMDB IDHMDB0006806
Secondary Accession Numbers
  • HMDB06806
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
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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.85 m³·mol⁻¹ChemAxon
Polarizability35.81 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lya-5913000000-c9cc25ab5bf7cdb806abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01r2-8923410000-ad6814a72184f59e8542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5914100000-91cfd0c5b4d29b3488b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-16aca9edc0f28599b061View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-2e68af310b047b1bdb7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4904300000-5d204fda744d81dc0866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-6900000000-dd107e3714dfcd94b540View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-0396a7faf046b6610b7aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Malonic AciduriaPw000207Pw000207 greyscalePw000207 simpleNot Available
Malonyl-coa decarboxylase deficiencyPw000478Pw000478 greyscalePw000478 simpleNot Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersPw000208Pw000208 greyscalePw000208 simpleNot Available
Propanoate MetabolismPw000149Pw000149 greyscalePw000149 simpleMap00640
Displaying all 4 entries
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
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

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
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
General function:
Involved in acetate-CoA ligase activity
Specific function:
Not Available
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Molecular weight:
59346.4
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