Np mrd loader

Record Information
Version2.0
Created at2022-03-17 19:47:10 UTC
Updated at2022-03-17 19:47:10 UTC
NP-MRD IDNP0046025
Secondary Accession NumbersNone
Natural Product Identification
Common NameMorin
DescriptionMorin, 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).
Structure
Thumb
Synonyms
ValueSource
2',3,4',5,7-PentahydroxyflavoneChEBI
2',4',3,5,7-PentahydroxyflavoneChEBI
2',4',5,7-Tetrahydroxyflavan-3-olChEBI
2',4',5,7-TetrahydroxyflavonolChEBI
2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
3,5,7,2',4'-PentahydroxyflavoneChEBI
C.I.Natural yellow 8ChEBI
2',3,4',5,7-Pentahydroxy-flavoneHMDB
2',4',5, 7-Tetrahydroxyflavan-3-olHMDB
2'-Hydroxypelargidenolon 1522HMDB
2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-oneHMDB
3,5 7 2 4-PentahydroxyflavoneHMDB
3,5,7,2',4'-PentahydroxyflavonolHMDB
Al-morinHMDB
AuranticaHMDB
Bois D,arcHMDB
C.I. 75660HMDB
C.I. natural yellow 11HMDB
C.I. natural yellow 8HMDB
Calico yellowHMDB
Morin hydrateHMDB
Morin, reagHMDB
Osage orangeHMDB
Osage orange crystalsHMDB
Osage orange extractHMDB
Toxylon pomiferumHMDB
3,2',4',5,7-PentahydroxyflavoneMeSH
Chemical FormulaC15H10O7
Average Mass302.2357 Da
Monoisotopic Mass302.04265 Da
IUPAC Name2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
Traditional Namebois d,arc
CAS Registry Number480-16-0
SMILES
OC1=CC(O)=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
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
InChI KeyYXOLAZRVSSWPPT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artocarpus champedenPlant
Chlorophora tinctoriaPlant
Chrysanthemum morifoliumLOTUS Database
Crotalaria assamicaPlant
Crotalaria pallidaPlant
Endosamara racemosaLOTUS Database
Fragaria x ananassaFooDB
Lannea coromandelicaPlant
Machilus bombycinaPlant
Maclura cochinchinensisLOTUS Database
Maclura pomiferaLOTUS Database
Maclura tinctoriaPlant
Maclura tricuspidataLOTUS Database
Millettia racemosaPlant
Morus albaPlant
Morus serrataPlant
Petasites formosanusLOTUS Database
Psidium guajavaPlant
Ribes nigrumFooDB
Ribes rubrumFooDB
Tilia tomentosaLOTUS Database
Toxicodendron vernicifluumLOTUS Database
Treculia africanaPlant
Vaccinium myrtillusFooDB
Vaccinium oxycoccosFooDB
Vaccinium vitis-idaeaFooDB
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.23ALOGPS
logP2.16ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.86 m³·mol⁻¹ChemAxon
Polarizability28.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030796
DrugBank IDNot Available
Phenol Explorer Compound ID310
FoodDB IDFDB002736
KNApSAcK IDC00004624
Chemspider ID4444989
KEGG Compound IDC10105
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMorin_(flavonol)
METLIN IDNot Available
PubChem Compound5281670
PDB IDNot Available
ChEBI ID75092
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]