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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:45 UTC

HMDB ID

HMDB0001494

Secondary Accession Numbers

HMDB01494

Metabolite Identification

Common Name

Acetylphosphate

Description

Acetylphosphate, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetic acid, monoanhydride with phosphoric acid	ChEBI
Acetyl phosphate	ChEBI
Acetylphosphoric acid	ChEBI
Monoacetyl phosphate	ChEBI
Acetate, monoanhydride with phosphate	Generator
Acetyl phosphoric acid	Generator
Monoacetyl phosphoric acid	Generator
Acetyl-p	HMDB

Chemical Formula

C₂H₅O₅P

Average Molecular Weight

140.0319

Monoisotopic Molecular Weight

139.987459782

IUPAC Name

(acetyloxy)phosphonic acid

Traditional Name

acetylphosphate

CAS Registry Number

590-54-5

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 Key

LIPOUNRJVLNBCD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Acyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

acyl monophosphate (CHEBI:15350 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001494)

Organ

Placenta (HMDB: HMDB0001494)

Source

Endogenous

Endogenous (HMDB: HMDB0001494)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (HMDB: HMDB0001494)
Acetate Metabolism (PathBank: SMP0002102)
Pyruvate Metabolism (HMDB: HMDB0001494)

Disease pathway

Leigh Syndrome (PathBank: SMP0000196)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0000334)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0000212)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0000558)
Pyruvate Kinase Deficiency (PathBank: SMP0000559)

Role

Biological role

Energy source (HMDB: HMDB0001494)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001494)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.8 g/L	ALOGPS
logP	-0.92	ALOGPS
logP	-0.88	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	1.24	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.8 m³·mol⁻¹	ChemAxon
Polarizability	9.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.004	31661259
DarkChem	[M-H]-	121.701	31661259
AllCCS	[M+H]+	132.797	32859911
AllCCS	[M-H]-	125.159	32859911
DeepCCS	[M+H]+	113.395	30932474
DeepCCS	[M-H]-	110.622	30932474
DeepCCS	[M-2H]-	147.258	30932474
DeepCCS	[M+Na]+	121.906	30932474
AllCCS	[M+H]+	132.8	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylphosphate	CC(=O)OP(O)(O)=O	2063.2	Standard polar	33892256
Acetylphosphate	CC(=O)OP(O)(O)=O	1101.9	Standard non polar	33892256
Acetylphosphate	CC(=O)OP(O)(O)=O	1163.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetylphosphate,1TMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C	1159.4	Semi standard non polar	33892256
Acetylphosphate,1TMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C	1214.7	Standard non polar	33892256
Acetylphosphate,1TMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C	1627.9	Standard polar	33892256
Acetylphosphate,2TMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1257.4	Semi standard non polar	33892256
Acetylphosphate,2TMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1360.7	Standard non polar	33892256
Acetylphosphate,2TMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1422.7	Standard polar	33892256
Acetylphosphate,1TBDMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	1424.8	Semi standard non polar	33892256
Acetylphosphate,1TBDMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	1463.0	Standard non polar	33892256
Acetylphosphate,1TBDMS,isomer #1	CC(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	1777.8	Standard polar	33892256
Acetylphosphate,2TBDMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1668.6	Semi standard non polar	33892256
Acetylphosphate,2TBDMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1795.6	Standard non polar	33892256
Acetylphosphate,2TBDMS,isomer #1	CC(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1730.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylphosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-cfae3a8437091232f5d7	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylphosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-9100000000-69d8c7734c01156379c8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004i-9000000000-2f22bf3e8b4d114a56d4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetylphosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ufr-9000000000-55ffd7f2d3597806d481	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 10V, Positive-QTOF	splash10-0002-9100000000-9815fa392fb818a6fab2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 20V, Positive-QTOF	splash10-0002-9000000000-f9f47252b65adfe6b7ab	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 40V, Positive-QTOF	splash10-000w-9000000000-aee29878b0aaf31375ca	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 10V, Negative-QTOF	splash10-004i-9200000000-30c93bbfd1e1c181a0bd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 20V, Negative-QTOF	splash10-004i-9000000000-3f8df70a36020543d1d7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-5ee765f8651dddb71d5c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 10V, Positive-QTOF	splash10-0002-9400000000-ca4664e711accab93652	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 20V, Positive-QTOF	splash10-000w-9000000000-bc91304aa950da45006b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 40V, Positive-QTOF	splash10-0006-9000000000-c51eac598b2179e94478	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 10V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Pyruvate metabolism	Not Available
Leigh Syndrome		Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)		Not Available
Pyruvate Dehydrogenase Complex Deficiency		Not Available
Primary hyperoxaluria II, PH2		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02897

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6278

PubChem Compound

186

PDB ID

Not Available

ChEBI ID

15350

Food Biomarker Ontology

Not Available

VMH ID

ACTP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Costakel, 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

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 ]
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 ]
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

Enzyme Details

1. Acylphosphatase-2

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 + Phosphate	details

Enzyme Details

2. Acylphosphatase-1

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 + Phosphate	details

Showing metabocard for Acetylphosphate (HMDB0001494)

MOL for HMDB0001494 (Acetylphosphate)

3D MOL for HMDB0001494 (Acetylphosphate)

3D SDF for HMDB0001494 (Acetylphosphate)

3D-SDF for HMDB0001494 (Acetylphosphate)

PDB for HMDB0001494 (Acetylphosphate)

3D PDB for HMDB0001494 (Acetylphosphate)

SMILES for HMDB0001494 (Acetylphosphate)

INCHI for HMDB0001494 (Acetylphosphate)

Structure for HMDB0001494 (Acetylphosphate)

3D Structure for HMDB0001494 (Acetylphosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions