| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:13:23 UTC |
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| Update date | 2019-11-26 03:15:26 UTC |
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| Primary ID | FDB017920 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Brevifolincarboxylic acid |
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| Description | Brevifolincarboxylic acid belongs to isocoumarins and derivatives class of compounds. Those are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Brevifolincarboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Brevifolincarboxylic acid can be found in pomegranate, which makes brevifolincarboxylic acid a potential biomarker for the consumption of this food product. |
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| CAS Number | 18490-95-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 7,8,9-Trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylate | Generator | | Brevifolincarboxylate | Generator | | 1,2,3,5-Tetrahydro-7,8,9-trihydroxy-3,5-dioxocyclopenta[c][2]benzopyran-1-carboxylic acid, 9CI | db_source |
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| Predicted Properties | |
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| Chemical Formula | C13H8O8 |
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| IUPAC name | 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylic acid |
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| InChI Identifier | InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19) |
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| InChI Key | JFJWMFPFMLRLMI-UHFFFAOYSA-N |
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| Isomeric SMILES | OC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2 |
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| Average Molecular Weight | 292.1978 |
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| Monoisotopic Molecular Weight | 292.021917232 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Isocoumarins and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Isocoumarins and derivatives |
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| Alternative Parents | |
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| Substituents | - Isocoumarin
- Benzopyran
- 2-benzopyran
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Ketone
- Lactone
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 53.44%; H 2.76%; O 43.80% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]13D -3 (c, 0.4 in Me2CO aq.) | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0090000000-cd6aa32eaf9d781d35d0 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-0090000000-4cde1c4215e89f9a8498 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00ns-0490000000-6174a5c8838ac2ebf1ba | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-0090000000-f21cea4ae3fdd3aef342 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0005-0090000000-d65709c1294d2858e81b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0v4i-9780000000-9936ba5327bf9afed16b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0090000000-3cd18dc695d7c34ba306 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002g-0090000000-3025667ae85facff20d4 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kb-0290000000-b500d211f8e61fd40bc9 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-7c929db8e418c0ef1780 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0090000000-8e37fba5799256353f59 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06y9-0960000000-dad569be1c17f3e250fb | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | LBT56-H:LBT56-H |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | BREVIFOLIN-CARBOXYLIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference |
- Navindra P. Seeram et al., “Section 1, Chapter 1 – Pomegranate Phytochemicals,” in Pomegranates: ancient roots to modern medicine (CRC Press, 2006), 3-30. [Structure]
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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