ECMDB: Acetylphosphate (ECMDB01494) (M2MDB000402)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (1005)

Record Information

Version

2.0

Creation Date

2012-05-31 13:53:34 -0600

Update Date

2015-09-13 12:56:11 -0600

Secondary Accession Numbers

ECMDB01494

Identification

Name:

Acetylphosphate

Description

Acetylphosphate is an intermediate in taurine and hypotaurine metabolism. 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. It is also intermediate in pyruvate metabolism. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Acetyl phosphate
Acetyl phosphoric acid
Acetyl-P
Acetylphosphate
Acetylphosphoric acid

Chemical Formula:

C₂H₅O₅P

Weight:

Average: 140.0319
Monoisotopic: 139.987459782

InChI Key:

LIPOUNRJVLNBCD-UHFFFAOYSA-N

InChI:

InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)

CAS number:

590-54-5

IUPAC Name:

(acetyloxy)phosphonic acid

Traditional IUPAC Name:

acetylphosphate

SMILES:

CC(=O)OP(O)(O)=O

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 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Acetyl-CoA + Phosphate <> Acetylphosphate + Coenzyme A
Acetic acid + Adenosine triphosphate <> Acetylphosphate + ADP
Acetylphosphate + Water <> Acetic acid + Phosphate
Adenosine triphosphate + Acetic acid > ADP + Acetylphosphate
Acetyl-CoA + Inorganic phosphate > CoA + Acetylphosphate
Acetyl-CoA + Phosphate > Coenzyme A + Acetylphosphate
Acetylphosphate + ADP > Adenosine triphosphate + Acetic acid
Acetyl-CoA + Phosphate <> Acetylphosphate + Coenzyme A
Acetic acid + Adenosine triphosphate <> Acetylphosphate + ADP
Acetic acid + Adenosine triphosphate <> Acetylphosphate + ADP

SMPDB Pathways:

Acetate metabolism	PW002090
Propanoate metabolism	PW000940

KEGG Pathways:

Metabolic pathways eco01100
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120
Propanoate metabolism ec00640
Pyruvate metabolism ec00620
Reductive carboxylate cycle (CO2 fixation) ec00720
Taurine and hypotaurine metabolism ec00430

EcoCyc Pathways:

acetate formation from acetyl-CoA I PWY0-1312
mixed acid fermentation FERMENTATION-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
1070± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
1050± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
1560± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-cfae3a8437091232f5d7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-9100000000-69d8c7734c01156379c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-2f22bf3e8b4d114a56d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-9000000000-55ffd7f2d3597806d481	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9100000000-9815fa392fb818a6fab2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-f9f47252b65adfe6b7ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000w-9000000000-aee29878b0aaf31375ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9200000000-30c93bbfd1e1c181a0bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-3f8df70a36020543d1d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5ee765f8651dddb71d5c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9400000000-ca4664e711accab93652	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000w-9000000000-bc91304aa950da45006b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c51eac598b2179e94478	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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)

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Links

External Links:

Resource	Link
CHEBI ID	15350
HMDB ID	HMDB01494
Pubchem Compound ID	186
Kegg ID	C00227
ChemSpider ID	181
Wikipedia ID	Not Available
BioCyc ID	ACETYL-P
EcoCyc ID	ACETYL-P
Ligand Expo	UVW

Enzymes

Protein Details

1. Acetate kinase

General function:: Involved in kinase activity
Specific function:: Involved in the activation of acetate to acetyl CoA and the secretion of acetate. During anaerobic growth of the organism, this enzyme is also involved in the synthesis of most of the ATP formed catabolically
Gene Name:: ackA
Uniprot ID:: P0A6A3
Molecular weight:: 43290

Reactions

ATP + acetate = ADP + acetyl phosphate.
ATP + propanoate = ADP + propanoyl phosphate.

Protein Details

2. Phosphate acetyltransferase

General function:: Involved in phosphate acetyltransferase activity
Specific function:: Acetyl-CoA + phosphate = CoA + acetyl phosphate
Gene Name:: pta
Uniprot ID:: P0A9M8
Molecular weight:: 77171

Reactions

Acetyl-CoA + phosphate = CoA + acetyl phosphate.

Protein Details

3. Acylphosphatase

General function:: Involved in acylphosphatase activity
Specific function:: An acylphosphate + H(2)O = a carboxylate + phosphate
Gene Name:: yccX
Uniprot ID:: P0AB65
Molecular weight:: 10300

Reactions

An acylphosphate + H(2)O = a carboxylate + phosphate.

Protein Details

4. Propionate kinase

General function:: Involved in kinase activity
Specific function:: ATP + propanoate = ADP + propanoyl phosphate
Gene Name:: tdcD
Uniprot ID:: P11868
Molecular weight:: 43384

Reactions

ATP + propanoate = ADP + propanoyl phosphate.
ATP + acetate = ADP + acetyl phosphate.

Protein Details

5. Phosphoribosylglycinamide formyltransferase 2

General function:: Involved in ATP binding
Specific function:: Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:: purT
Uniprot ID:: P33221
Molecular weight:: 42433

Reactions

Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.

Protein Details

6. Ethanolamine utilization protein eutD

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Specific function unknown
Gene Name:: eutD
Uniprot ID:: P77218
Molecular weight:: 36066

Acetylphosphate (ECMDB01494) (M2MDB000402)

Structure for #<Compound:0x6fbd48bc>

Enzymes

Reactions

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