Record Information |
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Version | 1.0 |
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Created at | 2021-06-22 16:43:16 UTC |
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Updated at | 2021-06-22 16:53:18 UTC |
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NP-MRD ID | NP0043769 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Xanthohumol B |
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Description | Xanthohumol B belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, xanthohumol b is considered to be a flavonoid. Xanthohumol B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Xanthohumol B is found in Humulus lupulus. It was first documented in 1997 (PMID: 9366096). Based on a literature review a small amount of articles have been published on Xanthohumol B (PMID: 15679315) (PMID: 10418944) (PMID: 10737704) (PMID: 23947133). |
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Structure | COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C1 InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+ |
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Synonyms | Value | Source |
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Dehydrocycloxanthohumol hydrate | ChEBI | rac-(e)-1-(3,5-Dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one | ChEBI | rac-6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone | ChEBI | rac-6-[3,4-Dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-one | ChEBI | Dehydrocycloxanthohumol hydric acid | Generator | 6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone | HMDB |
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Chemical Formula | C21H22O6 |
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Average Mass | 370.3958 Da |
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Monoisotopic Mass | 370.14164 Da |
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IUPAC Name | (2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one |
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Traditional Name | xanthohumol B |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C1 |
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InChI Identifier | InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+ |
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InChI Key | GUQGMEWOCKDLDE-RMKNXTFCSA-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, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated) | 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 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Linear 1,3-diarylpropanoids |
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Sub Class | Chalcones and dihydrochalcones |
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Direct Parent | 2'-Hydroxychalcones |
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Alternative Parents | |
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Substituents | - 2'-hydroxychalcone
- Hydroxycinnamic acid or derivatives
- 2,2-dimethyl-1-benzopyran
- Chromane
- Benzopyran
- 1-benzopyran
- Anisole
- Styrene
- Aryl ketone
- Alkyl aryl ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- Enone
- Secondary alcohol
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Tabata N, Ito M, Tomoda H, Omura S: Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus. Phytochemistry. 1997 Oct;46(4):683-7. doi: 10.1016/s0031-9422(97)00157-x. [PubMed:9366096 ]
- Zhao F, Watanabe Y, Nozawa H, Daikonnya A, Kondo K, Kitanaka S: Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). J Nat Prod. 2005 Jan;68(1):43-9. doi: 10.1021/np0499113. [PubMed:15679315 ]
- Miranda CL, Stevens JF, Helmrich A, Henderson MC, Rodriguez RJ, Yang YH, Deinzer ML, Barnes DW, Buhler DR: Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem Toxicol. 1999 Apr;37(4):271-85. doi: 10.1016/s0278-6915(99)00019-8. [PubMed:10418944 ]
- Miranda CL, Aponso GL, Stevens JF, Deinzer ML, Buhler DR: Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Lett. 2000 Feb 28;149(1-2):21-9. doi: 10.1016/s0304-3835(99)00328-6. [PubMed:10737704 ]
- Zhang WK, Wang SB, Fu CY, Li P, Xu JK: [Flavonoids from Humulus lupulus]. Zhongguo Zhong Yao Za Zhi. 2013 May;38(10):1539-42. [PubMed:23947133 ]
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