Hmdb loader
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
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:30:00 UTC
Update Date2021-09-14 14:57:49 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 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. 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; which is catalyzed by the enzyme acetyl-coenzyme A synthetase 2-like, mitochondrial. A purine ribonucleoside 5'-monophosphate consisting of adenosine 5'-monophosphate where one of the hydroxy groups of the phosphate has been condensed with propionic acid. 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 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent5'-acylphosphoadenosines
Alternative Parents
Substituents
  • 5'-acylphosphoadenosine
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Acyl phosphate
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Monosaccharide
  • Pyrimidine
  • N-substituted imidazole
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • 1,2-diol
  • Amino acid or derivatives
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic salt
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Primary amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.99 g/LALOGPS
logP10(-2) g/LALOGPS
logP10(-4) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.10331661259
DarkChem[M-H]-189.02731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propinol adenylate,1TMS,#1CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3288.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TMS,#2CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3290.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TMS,#3CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3306.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TMS,#4CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3340.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#1CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3197.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#2CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3222.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#3CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3236.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#4CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3233.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#5CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3235.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#6CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C3268.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TMS,#7CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3255.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TBDMS,#1CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3503.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TBDMS,#2CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3506.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TBDMS,#3CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3512.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,1TBDMS,#4CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3524.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#1CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3591.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#2CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)O[Si](C)(C)C(C)(C)C3597.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#3CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3584.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#4CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3611.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#5CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3589.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#6CCC(=O)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3618.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Propinol adenylate,2TBDMS,#7CCC(=O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3649.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Propinol adenylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lya-5913000000-c9cc25ab5bf7cdb806ab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propinol adenylate GC-MS (2 TMS) - 70eV, Positivesplash10-01r2-8923410000-ad6814a72184f59e85422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propinol adenylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propinol adenylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 10V, Positive-QTOFsplash10-000i-5914100000-91cfd0c5b4d29b3488b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 20V, Positive-QTOFsplash10-000i-3900000000-16aca9edc0f28599b0612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 40V, Positive-QTOFsplash10-000i-2900000000-2e68af310b047b1bdb7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 10V, Negative-QTOFsplash10-001i-4904300000-5d204fda744d81dc08662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 20V, Negative-QTOFsplash10-003r-6900000000-dd107e3714dfcd94b5402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 40V, Negative-QTOFsplash10-003r-9500000000-0396a7faf046b6610b7a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 10V, Positive-QTOFsplash10-0002-0309300000-552e044f229a538160dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 20V, Positive-QTOFsplash10-000i-1910000000-3030d909025ec83d805c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 40V, Positive-QTOFsplash10-000i-2900000000-25b5fd21f4d139eaa4f52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 10V, Negative-QTOFsplash10-004i-4009300000-68e440eecae9e4f483172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 20V, Negative-QTOFsplash10-004i-9000000000-461bd77745c544eb03d12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propinol adenylate 40V, Negative-QTOFsplash10-004i-9101000000-f61d576d5d36bebef4672021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
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