Record Information |
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Version | 1.0 |
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Created at | 2012-09-12 02:18:36 UTC |
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Updated at | 2021-08-19 23:58:55 UTC |
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NP-MRD ID | NP0001214 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Phenyl acetate |
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Description | Phenyl acetate, also known as acetylphenol, is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity. Naturally occurring in mammals, phenylacetate induces differentiation, growth inhibition, and apoptosis in tumor cells. Its mechanisms of action include decreased protein prenylation, activation of the peroxisome proliferation-activated receptors, inhibition of DNA methylation, and depletion of glutamine. Phenyl acetate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Phenyl acetate has a phenolic-like taste. |
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Structure | InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3 |
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Synonyms | Value | Source |
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Acetic acid,phenyl ester | ChEBI | Acetylphenol | ChEBI | Phenol acetate | ChEBI | Acetate,phenyl ester | Generator | Phenol acetic acid | Generator | Phenyl acetic acid | Generator | Acetates | HMDB | Acetic acid phenyl ester | HMDB | Acetic acid, phenyl ester | HMDB | Acetoxybenzene | HMDB | Acetyl phenol | HMDB | FEMA 3958 | HMDB | Fenylester kyseliny octove | HMDB | Phenyl ester OF acetic acid | HMDB |
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Chemical Formula | C8H8O2 |
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Average Mass | 136.1479 Da |
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Monoisotopic Mass | 136.05243 Da |
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IUPAC Name | phenyl acetate |
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Traditional Name | phenyl acetate |
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CAS Registry Number | 122-79-2 |
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SMILES | CC(=O)OC1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3 |
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InChI Key | IPBVNPXQWQGGJP-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenol esters |
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Sub Class | Not Available |
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Direct Parent | Phenol esters |
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Alternative Parents | |
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Substituents | - Phenol ester
- Phenoxy compound
- Monocyclic benzene moiety
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Liquid |
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Experimental Properties | |
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Predicted Properties | |
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External Links |
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HMDB ID | HMDB0040733 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB020542 |
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KNApSAcK ID | C00053673 |
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Chemspider ID | 28969 |
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KEGG Compound ID | C15583 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Phenyl_acetate |
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METLIN ID | Not Available |
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PubChem Compound | 31229 |
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PDB ID | Not Available |
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ChEBI ID | 8082 |
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Good Scents ID | rw1099401 |
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References |
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General References | - Miller AC, Xu J, Stewart M, McClain D: Suppression of depleted uranium-induced neoplastic transformation of human cells by the phenyl fatty acid, phenyl acetate: chemoprevention by targeting the p21RAS protein pathway. Radiat Res. 2001 Jan;155(1 Pt 2):163-170. doi: 10.1667/0033-7587(2001)155[0163:soduin]2.0.co;2. [PubMed:11121229 ]
- Munoz-Tello P, Lin H, Khan P, de Vera IMS, Kamenecka TM, Kojetin DJ: Assessment of NR4A Ligands That Directly Bind and Modulate the Orphan Nuclear Receptor Nurr1. J Med Chem. 2020 Dec 24;63(24):15639-15654. doi: 10.1021/acs.jmedchem.0c00894. Epub 2020 Dec 8. [PubMed:33289551 ]
- Bharti C, Sharma S, Goswami N, Sharma H, Rabbani SA, Kumar S: Role of nitazoxanide as a repurposed drug in the treatment and management of various diseases. Drugs Today (Barc). 2021 Jul;57(7):455-473. doi: 10.1358/dot.2021.57.7.3235211. [PubMed:34268533 ]
- Perla-Kajan J, Wloczkowska O, Ziola-Frankowska A, Frankowski M, Smith AD, de Jager CA, Refsum H, Jakubowski H: Paraoxonase 1, B Vitamins Supplementation, and Mild Cognitive Impairment. J Alzheimers Dis. 2021;81(3):1211-1229. doi: 10.3233/JAD-210137. [PubMed:33935094 ]
- Vijay K, Kiran GS, Divya S, Thangavel K, Thangavelu S, Dhandapani R, Selvin J: Fatty Acid Methyl Esters From the Coral-Associated Bacterium Pseudomonas aeruginosa Inhibit Virulence and Biofilm Phenotypes in Multidrug Resistant Staphylococcus aureus: An in vitro Approach. Front Microbiol. 2021 Mar 23;12:631853. doi: 10.3389/fmicb.2021.631853. eCollection 2021. [PubMed:33833739 ]
- Santos SC, La Scala JJ, Palmese GR: Effect of Microcapsule Content on Diels-Alder Room Temperature Self-Healing Thermosets. Polymers (Basel). 2020 Dec 21;12(12). pii: polym12123064. doi: 10.3390/polym12123064. [PubMed:33371328 ]
- Parada-Turska J, Wojcicka G, Beltowski J: Paraoxonase 1 Phenotype and Protein N-Homocysteinylation in Patients with Rheumatoid Arthritis: Implications for Cardiovascular Disease. Antioxidants (Basel). 2020 Sep 21;9(9). pii: antiox9090899. doi: 10.3390/antiox9090899. [PubMed:32967340 ]
- Mitra M, Nguyen KM, Box TW, Gilpin JS, Hamby SR, Berry TL, Duckett EH: Isolation and characterization of a novel bacterial strain from a Tris-Acetate-Phosphate agar medium plate of the green micro-alga Chlamydomonas reinhardtii that can utilize common environmental pollutants as a carbon source. F1000Res. 2020 Jun 29;9:656. doi: 10.12688/f1000research.24680.1. eCollection 2020. [PubMed:32855811 ]
- Baker JG, Fromont C, Bruder M, Thompson KSJ, Kellam B, Hill SJ, Gardiner SM, Fischer PM: Using Esterase Selectivity to Determine the In Vivo Duration of Systemic Availability and Abolish Systemic Side Effects of Topical beta-Blockers. ACS Pharmacol Transl Sci. 2020 Jul 1;3(4):737-748. doi: 10.1021/acsptsci.0c00051. eCollection 2020 Aug 14. [PubMed:32832874 ]
- Fernando HSD, Saavedra-Rodriguez K, Perera R, Black WC 4th, De Silva BGDNK: Resistance to commonly used insecticides and underlying mechanisms of resistance in Aedes aegypti (L.) from Sri Lanka. Parasit Vectors. 2020 Aug 10;13(1):407. doi: 10.1186/s13071-020-04284-y. [PubMed:32778147 ]
- Ganguly S, Mayans J, Ghosh A: Modulation of Nuclearity in Cu(II) -Mn(II) Complexes of a N2 O2 Donor Ligand Depending upon Carboxylate Anions: Structures, Magnetic Properties and Catalytic Oxidase Activities. Chem Asian J. 2020 Dec 1;15(23):4055-4069. doi: 10.1002/asia.202000706. Epub 2020 Oct 28. [PubMed:32722886 ]
- Matsumoto AK, Maes M, Supasitthumrong T, Maes A, Michelin AP, de Oliveira Semeao L, de Lima Pedrao JV, Moreira EG, Kanchanatawan B, Barbosa DS: Deficit schizophrenia and its features are associated with PON1 Q192R genotypes and lowered paraoxonase 1 (PON1) enzymatic activity: effects on bacterial translocation. CNS Spectr. 2021 Aug;26(4):406-415. doi: 10.1017/S1092852920001388. Epub 2020 Jun 23. [PubMed:32638685 ]
- Hong Y, Che X, Su H, Mai Z, Huang Z, Huang W, Chen W, Liu S, Gao W, Zhou Z, Tan G, Li X: Exhaled breath analysis using on-line preconcentration mass spectrometry for gastric cancer diagnosis. J Mass Spectrom. 2021 Apr;56(4):e4588. doi: 10.1002/jms.4588. Epub 2020 Jul 7. [PubMed:32633879 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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