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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:23:25 UTC |
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HMDB ID | HMDB0001494 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Acetylphosphate |
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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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. rep. populaire Roumaine (1960), 5 7-10). Cancerous serum produced 37% less acetylphosphate than normal serum. |
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Structure | |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C2H5O5P |
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Average Molecular Weight | 140.0319 |
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Monoisotopic Molecular Weight | 139.987459782 |
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IUPAC Name | (acetyloxy)phosphonic acid |
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Traditional Name | acetylphosphate |
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CAS Registry Number | 590-54-5 |
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SMILES | CC(=O)OP(O)(O)=O |
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InChI Identifier | InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6) |
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InChI Key | LIPOUNRJVLNBCD-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphoric acids and derivatives |
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Sub Class | Phosphate esters |
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Direct Parent | Acyl monophosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9000000000-cfae3a8437091232f5d7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-9100000000-69d8c7734c01156379c8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9000000000-2f22bf3e8b4d114a56d4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ufr-9000000000-55ffd7f2d3597806d481 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9100000000-9815fa392fb818a6fab2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-f9f47252b65adfe6b7ab | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000w-9000000000-aee29878b0aaf31375ca | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9200000000-30c93bbfd1e1c181a0bd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-3f8df70a36020543d1d7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-5ee765f8651dddb71d5c | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB02897 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022653 |
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KNApSAcK ID | C00019559 |
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Chemspider ID | 181 |
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KEGG Compound ID | C00227 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 6278 |
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PubChem Compound | 186 |
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PDB ID | Not Available |
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ChEBI ID | 15350 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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 ]
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