| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 19:47:10 UTC |
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| Updated at | 2022-03-17 19:47:10 UTC |
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| NP-MRD ID | NP0046025 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Morin |
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| Description | Morin, also known as al-morin or aurantica, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, morin is considered to be a flavonoid lipid molecule. Morin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Morin is a bitter tasting compound. Outside of the human body, Morin is found, on average, in the highest concentration within strawberries. Morin has also been detected, but not quantified in, several different foods, such as redcurrants, lingonberries, blackcurrants, fruits, and bilberries. This could make morin a potential biomarker for the consumption of these foods. Morin is found in Artocarpus integrifolia , Chlorophora tinctoria, Chrysanthemum morifolium, Crotalaria assamica, Crotalaria pallida , Endosamara racemosa, Lannea coromandelica , Machilus bombycina, Maclura cochinchinensis, Maclura pomifera, Morus tinctoria, Maclura tricuspidata, Millettia racemosa , Morus alba , Morus serrata , Petasites formosanus, Psidium guajava , Tilia tomentosa, Toxicodendron vernicifluum and Treculia africana . Morin was first documented in 2004 (PMID: 15516722). A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5 (PMID: 16806951) (PMID: 18629640) (PMID: 19539802) (PMID: 19774509) (PMID: 22740350) (PMID: 23030699). |
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| Structure | OC1=CC(O)=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H |
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| Synonyms | | Value | Source |
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| 2',3,4',5,7-Pentahydroxyflavone | ChEBI | | 2',4',3,5,7-Pentahydroxyflavone | ChEBI | | 2',4',5,7-Tetrahydroxyflavan-3-ol | ChEBI | | 2',4',5,7-Tetrahydroxyflavonol | ChEBI | | 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one | ChEBI | | 3,5,7,2',4'-Pentahydroxyflavone | ChEBI | | C.I.Natural yellow 8 | ChEBI | | 2',3,4',5,7-Pentahydroxy-flavone | HMDB | | 2',4',5, 7-Tetrahydroxyflavan-3-ol | HMDB | | 2'-Hydroxypelargidenolon 1522 | HMDB | | 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one, 9ci | HMDB | | 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one | HMDB | | 3,5 7 2 4-Pentahydroxyflavone | HMDB | | 3,5,7,2',4'-Pentahydroxyflavonol | HMDB | | Al-morin | HMDB | | Aurantica | HMDB | | Bois D,arc | HMDB | | C.I. 75660 | HMDB | | C.I. natural yellow 11 | HMDB | | C.I. natural yellow 8 | HMDB | | Calico yellow | HMDB | | Morin hydrate | HMDB | | Morin, reag | HMDB | | Osage orange | HMDB | | Osage orange crystals | HMDB | | Osage orange extract | HMDB | | Toxylon pomiferum | HMDB | | 3,2',4',5,7-Pentahydroxyflavone | MeSH |
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| Chemical Formula | C15H10O7 |
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| Average Mass | 302.2357 Da |
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| Monoisotopic Mass | 302.04265 Da |
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| IUPAC Name | 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one |
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| Traditional Name | bois d,arc |
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| CAS Registry Number | 480-16-0 |
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| SMILES | OC1=CC(O)=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 |
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| InChI Identifier | InChI=1S/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H |
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| InChI Key | YXOLAZRVSSWPPT-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | 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 | 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, 300 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, 400 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 | 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, 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 | 13C NMR Spectrum (1D, 201 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, 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 flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-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 | Flavonols |
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| Alternative Parents | |
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| Substituents | - 3-hydroxyflavone
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- 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 | - Kang DG, Moon MK, Sohn EJ, Lee DH, Lee HS: Effects of morin on blood pressure and metabolic changes in fructose-induced hypertensive rats. Biol Pharm Bull. 2004 Nov;27(11):1779-83. doi: 10.1248/bpb.27.1779. [PubMed:15516722 ]
- Gottlieb M, Leal-Campanario R, Campos-Esparza MR, Sanchez-Gomez MV, Alberdi E, Arranz A, Delgado-Garcia JM, Gruart A, Matute C: Neuroprotection by two polyphenols following excitotoxicity and experimental ischemia. Neurobiol Dis. 2006 Aug;23(2):374-86. doi: 10.1016/j.nbd.2006.03.017. Epub 2006 Jun 27. [PubMed:16806951 ]
- Lee HS, Jung KH, Park IS, Kwon SW, Lee DH, Hong SS: Protective effect of morin on dimethylnitrosamine-induced hepatic fibrosis in rats. Dig Dis Sci. 2009 Apr;54(4):782-8. doi: 10.1007/s10620-008-0404-x. Epub 2008 Jul 17. [PubMed:18629640 ]
- Sivaramakrishnan V, Niranjali Devaraj S: Morin regulates the expression of NF-kappaB-p65, COX-2 and matrix metalloproteinases in diethylnitrosamine induced rat hepatocellular carcinoma. Chem Biol Interact. 2009 Aug 14;180(3):353-9. doi: 10.1016/j.cbi.2009.02.004. Epub 2009 Feb 21. [PubMed:19539802 ]
- Jung HJ, Kim SJ, Song YS, Park EH, Lim CJ: Evaluation of the antiangiogenic, anti-inflammatory, and antinociceptive activities of morin. Planta Med. 2010 Feb;76(3):273-5. doi: 10.1055/s-0029-1186079. Epub 2009 Sep 11. [PubMed:19774509 ]
- Sahu K, Shaharyar M, Siddiqui AA: Effect of morin on pharmacokinetics of piracetam in rats, in vitro enzyme kinetics and metabolic stability assay using rapid UPLC method. Drug Test Anal. 2013 Jul;5(7):581-8. doi: 10.1002/dta.1382. Epub 2012 Jun 28. [PubMed:22740350 ]
- Maicheen C, Jittikoon J, Vajragupta O, Ungwitayatorn J: Synthesis, topoisomerase I inhibitory and cytotoxic activities of chromone derivatives. Med Chem. 2013 May;9(3):329-39. doi: 10.2174/1573406411309030003. [PubMed:23030699 ]
- Yang SH, Choi HG, Lim SJ, Lee MG, Kim SH: Effects of morin on the pharmacokinetics of etoposide in 7,12-dimethylbenz[a]anthracene-induced mammary tumors in female Sprague-Dawley rats. Oncol Rep. 2013 Mar;29(3):1215-23. doi: 10.3892/or.2012.2201. Epub 2012 Dec 19. [PubMed:23254912 ]
- Gupta SC, Phromnoi K, Aggarwal BB: Morin inhibits STAT3 tyrosine 705 phosphorylation in tumor cells through activation of protein tyrosine phosphatase SHP1. Biochem Pharmacol. 2013 Apr 1;85(7):898-912. doi: 10.1016/j.bcp.2012.12.018. Epub 2012 Dec 29. [PubMed:23279849 ]
- Paoli P, Cirri P, Caselli A, Ranaldi F, Bruschi G, Santi A, Camici G: The insulin-mimetic effect of Morin: a promising molecule in diabetes treatment. Biochim Biophys Acta. 2013 Apr;1830(4):3102-11. doi: 10.1016/j.bbagen.2013.01.017. Epub 2013 Jan 24. [PubMed:23352912 ]
- Abuohashish HM, Al-Rejaie SS, Al-Hosaini KA, Parmar MY, Ahmed MM: Alleviating effects of morin against experimentally-induced diabetic osteopenia. Diabetol Metab Syndr. 2013 Feb 6;5(1):5. doi: 10.1186/1758-5996-5-5. [PubMed:23384060 ]
- Spindler SR, Mote PL, Flegal JM, Teter B: Influence on longevity of blueberry, cinnamon, green and black tea, pomegranate, sesame, curcumin, morin, pycnogenol, quercetin, and taxifolin fed iso-calorically to long-lived, F1 hybrid mice. Rejuvenation Res. 2013 Apr;16(2):143-51. doi: 10.1089/rej.2012.1386. [PubMed:23432089 ]
- Liu CJ, Lin JY: Anti-inflammatory effects of phenolic extracts from strawberry and mulberry fruits on cytokine secretion profiles using mouse primary splenocytes and peritoneal macrophages. Int Immunopharmacol. 2013 Jun;16(2):165-70. doi: 10.1016/j.intimp.2013.03.032. Epub 2013 Apr 13. [PubMed:23590821 ]
- Woznicka E, Kuzniar A, Nowak D, Nykiel E, Kopacz M, Gruszecka J, Golec K: Comparative study on the antibacterial activity of some flavonoids and their sulfonic derivatives. Acta Pol Pharm. 2013 May-Jun;70(3):567-71. [PubMed:23757948 ]
- Lee J, Shin YK, Song JY, Lee KW: Protective mechanism of morin against ultraviolet B-induced cellular senescence in human keratinocyte stem cells. Int J Radiat Biol. 2014 Jan;90(1):20-8. doi: 10.3109/09553002.2013.835502. Epub 2013 Sep 13. [PubMed:23952478 ]
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