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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:30 UTC
HMDB IDHMDB0001494
Secondary Accession Numbers
  • HMDB01494
Metabolite Identification
Common NameAcetylphosphate
DescriptionAcetylphosphate, also known as acetyl-p, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. Since acetylphosphate synthesis is known to depend on cholinesterase activity, pseudocholinesterase was assumed to participate to a small extent in acetylphosphate synthesis by cancerous serum. It is also an intermediate in pyruvate metabolism. Acetylphosphate is a drug. Acetylphosphate exists in all living organisms, ranging from bacteria to humans. Acetylphosphate can be converted into acetic acid; which is mediated by the enzyme acylphosphatase-1. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). In humans, acetylphosphate is involved in the metabolic disorder called the pyruvate dehydrogenase complex deficiency pathway. It is generated from sulfoacetaldehyde, converted to acetyl-CoA and acetate via phosphate acetyltransferase (EC:2.3.1.8) and acetate kinase (EC:2.7.2.1) respectively. Acetylphosphate or actyl phosphate is a compound involved in taurine and hypotaurine metabolism as well as pyruvate metabolism. Cancerous serum produced 37% less acetylphosphate than normal serum.
Structure
Data?1582752205
Synonyms
ValueSource
Acetic acid, monoanhydride with phosphoric acidChEBI
Acetyl phosphateChEBI
Acetylphosphoric acidChEBI
Monoacetyl phosphateChEBI
Acetate, monoanhydride with phosphateGenerator
Acetyl phosphoric acidGenerator
Monoacetyl phosphoric acidGenerator
Acetyl-pHMDB
Chemical FormulaC2H5O5P
Average Molecular Weight140.0319
Monoisotopic Molecular Weight139.987459782
IUPAC Name(acetyloxy)phosphonic acid
Traditional Nameacetylphosphate
CAS Registry Number590-54-5
SMILES
CC(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
InChI KeyLIPOUNRJVLNBCD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Acetate salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.8 g/LALOGPS
logP-0.92ALOGPS
logP-0.88ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)1.24ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.8 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.00431661259
DarkChem[M-H]-121.70131661259
AllCCS[M+H]+132.79732859911
AllCCS[M-H]-125.15932859911
DeepCCS[M+H]+113.39530932474
DeepCCS[M-H]-110.62230932474
DeepCCS[M-2H]-147.25830932474
DeepCCS[M+Na]+121.90630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetylphosphateCC(=O)OP(O)(O)=O2063.2Standard polar33892256
AcetylphosphateCC(=O)OP(O)(O)=O1101.9Standard non polar33892256
AcetylphosphateCC(=O)OP(O)(O)=O1163.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetylphosphate,1TMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C1159.4Semi standard non polar33892256
Acetylphosphate,1TMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C1214.7Standard non polar33892256
Acetylphosphate,1TMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C1627.9Standard polar33892256
Acetylphosphate,2TMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1257.4Semi standard non polar33892256
Acetylphosphate,2TMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1360.7Standard non polar33892256
Acetylphosphate,2TMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1422.7Standard polar33892256
Acetylphosphate,1TBDMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C1424.8Semi standard non polar33892256
Acetylphosphate,1TBDMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C1463.0Standard non polar33892256
Acetylphosphate,1TBDMS,isomer #1CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C1777.8Standard polar33892256
Acetylphosphate,2TBDMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1668.6Semi standard non polar33892256
Acetylphosphate,2TBDMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1795.6Standard non polar33892256
Acetylphosphate,2TBDMS,isomer #1CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1730.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetylphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cfae3a8437091232f5d72017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylphosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-9100000000-69d8c7734c01156379c82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9000000000-2f22bf3e8b4d114a56d42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ufr-9000000000-55ffd7f2d3597806d4812012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 10V, Negative-QTOFsplash10-004i-9200000000-30c93bbfd1e1c181a0bd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 20V, Negative-QTOFsplash10-004i-9000000000-3f8df70a36020543d1d72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 40V, Negative-QTOFsplash10-004i-9000000000-5ee765f8651dddb71d5c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 10V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 10V, Positive-QTOFsplash10-0002-9100000000-9815fa392fb818a6fab22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 20V, Positive-QTOFsplash10-0002-9000000000-f9f47252b65adfe6b7ab2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 40V, Positive-QTOFsplash10-000w-9000000000-aee29878b0aaf31375ca2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 10V, Positive-QTOFsplash10-0002-9400000000-ca4664e711accab936522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 20V, Positive-QTOFsplash10-000w-9000000000-bc91304aa950da45006b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylphosphate 40V, Positive-QTOFsplash10-0006-9000000000-c51eac598b2179e944782021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02897
Phenol Explorer Compound IDNot Available
FooDB IDFDB022653
KNApSAcK IDC00019559
Chemspider ID181
KEGG Compound IDC00227
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6278
PubChem Compound186
PDB IDNot Available
ChEBI ID15350
Food Biomarker OntologyNot Available
VMH IDACTP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCostakel, O.; Kitzoulesco, I. The possibility of acetylphosphate synthesis in cancerous and noncancerous human serum at pH 4. Rev. sci. Med., Acad. rep. populaire Roumaine (1960), 5 7-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Libeer JC, Scharpe SL, Verkerk RM, Deprettere AJ, Schepens PJ: Simultaneous determination of p-aminobenzoic acid, acetyl-p-aminobenzoic acid and p-aminohippuric acid in serum and urine by capillary gas chromatography with use of a nitrogen-phosphorus detector. Clin Chim Acta. 1981 Sep 10;115(2):119-23. [PubMed:6974621 ]
  2. Dowling TC, Frye RF, Zemaitis MA: Simultaneous determination of p-aminohippuric acid, acetyl-p-aminohippuric acid and iothalamate in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Sep 25;716(1-2):305-13. [PubMed:9824245 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Acetylphosphate + Water → Acetic acid + Phosphatedetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Acetylphosphate + Water → Acetic acid + Phosphatedetails