Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:54:01 UTC |
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Update Date | 2022-03-07 02:53:36 UTC |
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HMDB ID | HMDB0033148 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Artocarpetin B |
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Description | Artocarpetin B belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, artocarpetin b is considered to be a flavonoid. Artocarpetin B has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make artocarpetin b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Artocarpetin B. |
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Structure | COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=C(OC)C=C(O)C=C1 InChI=1S/C22H22O6/c1-12(2)5-7-15-19(27-4)10-16(24)21-17(25)11-20(28-22(15)21)14-8-6-13(23)9-18(14)26-3/h5-6,8-11,23-24H,7H2,1-4H3 |
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Synonyms | Value | Source |
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4',5-Dihydroxy-2',7-dimethoxy-8-prenylflavone | HMDB | 5-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | HMDB |
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Chemical Formula | C22H22O6 |
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Average Molecular Weight | 382.4065 |
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Monoisotopic Molecular Weight | 382.141638436 |
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IUPAC Name | 5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
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Traditional Name | artocarpetin B |
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CAS Registry Number | 170894-22-1 |
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SMILES | COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=C(OC)C=C(O)C=C1 |
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InChI Identifier | InChI=1S/C22H22O6/c1-12(2)5-7-15-19(27-4)10-16(24)21-17(25)11-20(28-22(15)21)14-8-6-13(23)9-18(14)26-3/h5-6,8-11,23-24H,7H2,1-4H3 |
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InChI Key | AGQBGLZQKDLJAR-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavones |
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Direct Parent | 8-prenylated flavones |
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Alternative Parents | |
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Substituents | - 8-prenylated flavone
- 7-methoxyflavonoid-skeleton
- 2p-methoxyflavonoid-skeleton
- Hydroxyflavonoid
- 5-hydroxyflavonoid
- 4'-hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Methoxyphenol
- Methoxybenzene
- Anisole
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Pyranone
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Vinylogous acid
- Heteroaromatic compound
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 253 - 257 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.15 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Artocarpetin B,1TMS,isomer #1 | COC1=CC(O)=CC=C1C1=CC(=O)C2=C(O[Si](C)(C)C)C=C(OC)C(CC=C(C)C)=C2O1 | 3336.4 | Semi standard non polar | 33892256 | Artocarpetin B,1TMS,isomer #2 | COC1=CC(O[Si](C)(C)C)=CC=C1C1=CC(=O)C2=C(O)C=C(OC)C(CC=C(C)C)=C2O1 | 3384.0 | Semi standard non polar | 33892256 | Artocarpetin B,2TMS,isomer #1 | COC1=CC(O[Si](C)(C)C)=CC=C1C1=CC(=O)C2=C(O[Si](C)(C)C)C=C(OC)C(CC=C(C)C)=C2O1 | 3279.3 | Semi standard non polar | 33892256 | Artocarpetin B,1TBDMS,isomer #1 | COC1=CC(O)=CC=C1C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(CC=C(C)C)=C2O1 | 3572.1 | Semi standard non polar | 33892256 | Artocarpetin B,1TBDMS,isomer #2 | COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1=CC(=O)C2=C(O)C=C(OC)C(CC=C(C)C)=C2O1 | 3631.7 | Semi standard non polar | 33892256 | Artocarpetin B,2TBDMS,isomer #1 | COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(CC=C(C)C)=C2O1 | 3780.3 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Artocarpetin B GC-MS (Non-derivatized) - 70eV, Positive | splash10-0gb9-1019000000-c0159f00561abf01e36d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artocarpetin B GC-MS (2 TMS) - 70eV, Positive | splash10-03di-2010490000-07fe247875b7e92b8bfd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artocarpetin B GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 10V, Negative-QTOF | splash10-001i-0009000000-0803631ade48de4b1420 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 20V, Negative-QTOF | splash10-001i-0009000000-c338b8ad5727d0df0fbe | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 40V, Negative-QTOF | splash10-0080-2789000000-414f5ec4702e2d1a3c3b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 10V, Negative-QTOF | splash10-001i-0009000000-738554ec1bbdf9d6a64e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 20V, Negative-QTOF | splash10-00m0-0009000000-25749eb2ea2d4c5d9f0c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 10V, Positive-QTOF | splash10-001i-0009000000-73f9d4e63d735cc0c348 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 20V, Positive-QTOF | splash10-017i-2019000000-56aab6da79c6d4e10d58 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 40V, Positive-QTOF | splash10-016u-6393000000-e07815c547d35775106e | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 10V, Positive-QTOF | splash10-001i-0009000000-d94925a5a63c5ae35387 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 20V, Positive-QTOF | splash10-001i-0009000000-5507b8ecd5e2c43860e3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artocarpetin B 40V, Positive-QTOF | splash10-00r6-0249000000-3a721acf90ef48056d61 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011152 |
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KNApSAcK ID | C00013418 |
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Chemspider ID | 24843906 |
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KEGG Compound ID | Not Available |
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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 | Not Available |
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PubChem Compound | 15231525 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1833471 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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