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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:30:00 UTC
Update Date2020-02-26 21:26:47 UTC
HMDB IDHMDB0006806
Secondary Accession Numbers
  • HMDB06806
Metabolite Identification
Common NamePropinol adenylate
DescriptionPropinol adenylate, also known as propionyl-AMP, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Propinol adenylate is a strong basic compound (based on its pKa). Propinol adenylate exists in all living organisms, ranging from bacteria to humans. Within humans, propinol adenylate participates in a number of enzymatic reactions. In particular, propinol adenylate can be converted into propionic acid through the action of the enzyme acyl-CoA synthetase short-chain family member 3, mitochondrial. In addition, propinol adenylate can be converted into propionic acid through its interaction with the enzyme acetyl-coenzyme A synthetase 2-like, mitochondrial. In humans, propinol adenylate is involved in the metabolic disorder called methylmalonic aciduria due to cobalamin-related disorders.
Structure
Data?1582752407
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
5'-Adenylate propionate anhydrideGenerator
Propanoyl-adenosine monophosphoric acidGenerator
Propionyl-adenosine monophosphoric acidGenerator
Propionyladenylic acidGenerator
Propinol adenylic 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
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Monoalkyl phosphate
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lya-5913000000-c9cc25ab5bf7cdb806abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01r2-8923410000-ad6814a72184f59e8542Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5914100000-91cfd0c5b4d29b3488b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-16aca9edc0f28599b061Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-2e68af310b047b1bdb7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4904300000-5d204fda744d81dc0866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-6900000000-dd107e3714dfcd94b540Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-0396a7faf046b6610b7aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDHC01668
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