Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 18:26:32 UTC |
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Updated at | 2021-08-12 19:51:49 UTC |
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NP-MRD ID | NP0002671 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-Nitrocatechol |
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Provided By | BMRB |
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Description | 4-Nitrocatechol belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. 4-Nitrocatechol exists in all living organisms, ranging from bacteria to humans. 4-Nitrocatechol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1993 (PMID: 8267647). Based on a literature review a significant number of articles have been published on 4-Nitrocatechol (PMID: 17984079) (PMID: 8214571) (PMID: 14993710) (PMID: 20854995). |
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Structure | OC1=C(O)C=C(C=C1)[N+]([O-])=O InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H |
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Synonyms | Value | Source |
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1,2-Dihydroxy-4-nitrobenzene | ChEBI | 4-Nitropyrocatechol | ChEBI | 3,4-Dihydroxy-1-nitrobenzene | HMDB | 3,4-Dihydroxynitrobenzene | HMDB | 4-nitro-1,2-Benzenediol | HMDB | 4-nitro-1,2-Dihydroxybenzene | HMDB | 4-nitro-Pyrocatechol4-nitropyrocatechol NSC 80651 | HMDB | 4-Nitrobenzcatechin | HMDB | P-Nitrocatechol | HMDB | 2-Hydroxy-4-nitrophenolate | HMDB | 4-Nitro-1,2-benzenediol | HMDB | 4-Nitro-1,2-dihydroxybenzene | HMDB | 4-Nitrocatechol | HMDB | p-Nitrocatechol | HMDB |
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Chemical Formula | C6H5NO4 |
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Average Mass | 155.1082 Da |
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Monoisotopic Mass | 155.02186 Da |
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IUPAC Name | 4-nitrobenzene-1,2-diol |
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Traditional Name | 4-nitrocatechol |
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CAS Registry Number | Not Available |
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SMILES | OC1=C(O)C=C(C=C1)[N+]([O-])=O |
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InChI Identifier | InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H |
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InChI Key | XJNPNXSISMKQEX-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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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Nitrophenols |
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Direct Parent | Nitrophenols |
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Alternative Parents | |
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Substituents | - Nitrophenol
- Nitrobenzene
- Nitroaromatic compound
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- C-nitro compound
- Organic nitro compound
- Organic oxoazanium
- Allyl-type 1,3-dipolar organic compound
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- 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 | Not Available |
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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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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Tassaneeyakul W, Veronese ME, Birkett DJ, Gonzalez FJ, Miners JO: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem Pharmacol. 1993 Dec 3;46(11):1975-81. doi: 10.1016/0006-2952(93)90639-e. [PubMed:8267647 ]
- Duescher RJ, Elfarra AA: Determination of p-nitrophenol hydroxylase activity of rat liver microsomes by high-pressure liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):311-4. doi: 10.1006/abio.1993.1335. [PubMed:8214571 ]
- Skrzypczak-Jankun E, Borbulevych OY, Jankun J: Soybean lipoxygenase-3 in complex with 4-nitrocatechol. Acta Crystallogr D Biol Crystallogr. 2004 Mar;60(Pt 3):613-5. doi: 10.1107/S0907444904000861. Epub 2004 Feb 25. [PubMed:14993710 ]
- Lemley CO, Wilson ME: Effect of cytochrome P450 and aldo-keto reductase inhibitors on progesterone inactivation in primary bovine hepatic cell cultures. J Dairy Sci. 2010 Oct;93(10):4613-24. doi: 10.3168/jds.2010-3165. [PubMed:20854995 ]
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