Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-08-14 17:18:54 UTC |
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Update Date | 2020-02-26 21:26:52 UTC |
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HMDB ID | HMDB0006880 |
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Secondary Accession Numbers | - HMDB0006947
- HMDB06880
- HMDB06947
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Metabolite Identification |
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Common Name | Acetyl adenylate |
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Description | Acetyl adenylate, also known as acetyl AMP, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Acetyl adenylate is a strong basic compound (based on its pKa). |
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Structure | |
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Synonyms | Value | Source |
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5'-Acetylphosphoadenosine | Kegg | Acetyl adenylic acid | Generator | 5'-O-[Acetoxy(hydroxy)phosphoryl]adenosine | HMDB | Acetyl AMP | HMDB | Acetyladenylate | HMDB | [[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] acetate | HMDB |
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Chemical Formula | C12H16N5O8P |
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Average Molecular Weight | 389.2579 |
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Monoisotopic Molecular Weight | 389.073649025 |
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IUPAC Name | (acetyloxy)({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid |
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Traditional Name | 5'-acetylphosphoadenosine |
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CAS Registry Number | 13015-87-7 |
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SMILES | CC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N |
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InChI Identifier | InChI=1S/C12H16N5O8P/c1-5(18)25-26(21,22)23-2-6-8(19)9(20)12(24-6)17-4-16-7-10(13)14-3-15-11(7)17/h3-4,6,8-9,12,19-20H,2H2,1H3,(H,21,22)(H2,13,14,15)/t6-,8-,9-,12-/m1/s1 |
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InChI Key | UBPVOHPZRZIJHM-WOUKDFQISA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Bile acids, alcohols and derivatives |
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Direct Parent | Tetrahydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - 26-hydroxysteroid
- Tetrahydroxy bile acid, alcohol, or derivatives
- Sulfated steroid skeleton
- 3-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- 3-alpha-hydroxysteroid
- 7-hydroxysteroid
- Sulfate-ester
- Sulfuric acid monoester
- Alkyl sulfate
- Sulfuric acid ester
- Organic sulfuric acid or derivatives
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Organic oxide
- Primary alcohol
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Source: |
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Process | Naturally occurring process: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0gvt-5913000000-4b21305f5ae8862b482a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00pl-4891600000-9a73d48fc64423dadb41 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000j-1819000000-91af5d9e32b06642ebc1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0901000000-afcae5af796629b17092 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-b6122ae0e10da781cb2d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00c9-2809000000-bcbe596d9947ab374421 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-003r-4901000000-e99793fd821fb5ed2ce6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0059-9600000000-330dd6ff381223198137 | Spectrum |
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General References | - WEBSTER LT Jr: STUDIES OF THE ACETYL COENZYME A SYNTHETASE REACTION. I. ISOLATION AND CHARACTERIZATION OF ENZYME-BOUND ACETYL ADENYLATE. J Biol Chem. 1963 Dec;238:4010-5. [PubMed:14086739 ]
- Webster LT Jr: Studies of the acetyl coenzyme A synthetase reaction. V. The requirement for monovalent and divalent cations in partial reactions involving enzyme-bound acetyl adenylate. J Biol Chem. 1967 Mar 25;242(6):1232-40. [PubMed:4290317 ]
- Hilscher LW, Hanson CD, Russell DH, Raushel FM: Measurement of positional isotope exchange rates in enzyme-catalyzed reactions by fast atom bombardment mass spectrometry: application to argininosuccinate synthetase. Biochemistry. 1985 Oct 8;24(21):5888-93. [PubMed:2867775 ]
- Schmellenkamp H, Eggerer H: Mechanism of enzymic acetylation of des-acetyl citrate lyase. Proc Natl Acad Sci U S A. 1974 May;71(5):1987-91. [PubMed:4365579 ]
- Ramponi G, Manao G, Camici G: Nonenzymatic acetylation of histones with acetyl phosphate and acetyl adenylate. Biochemistry. 1975 Jun 17;14(12):2681-5. [PubMed:238571 ]
- Camici G, Manao G, Ramponi G: Nonenzymatic reactivation of des-acetyl citrate lyase by acetyl adenylate. First example of enzyme activation by chemotrophic modification. Physiol Chem Phys. 1975;7(5):409-14. [PubMed:698 ]
- Shewmaker CK, Wagner TE: Analysis of binding interactions between histone core complex and simian virus 40 DNA. A comparison of acetylated versus non-acetylated histone core complexes. Eur J Biochem. 1980 Jun;107(2):505-10. [PubMed:6249594 ]
- Cohen BN, Blue WT, Wagner TE: Chemically induced gene expression. Manipulation of the transforming ability of simian virus 40 minichromatin by specific chemical hyperacetylation of histones H3 and H4. Eur J Biochem. 1980 Jun;107(2):511-8. [PubMed:6249595 ]
- Krajewski WA, Luchnik AN: Relationship of histone acetylation to DNA topology and transcription. Mol Gen Genet. 1991 Dec;230(3):442-8. [PubMed:1662766 ]
- Krajewski WA: Effect of nonenzymatic histone acetylation on chromatin high-order folding. Biochem Biophys Res Commun. 1996 Apr 16;221(2):295-9. [PubMed:8619849 ]
- Wolfe AJ, Conley MP, Berg HC: Acetyladenylate plays a role in controlling the direction of flagellar rotation. Proc Natl Acad Sci U S A. 1988 Sep;85(18):6711-5. [PubMed:2901103 ]
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