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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:05 UTC
Update Date2019-07-23 06:07:19 UTC
HMDB IDHMDB0030796
Secondary Accession Numbers
  • HMDB30796
Metabolite 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. A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.
Structure
Data?1563862039
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 Molecular Weight302.2357
Monoisotopic Molecular Weight302.042652674
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point303 - 304 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.54Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0560-3953230000-e5cc9aec411435ccf00eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0560-3953230000-e5cc9aec411435ccf00eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0490000000-3a567ae73e283a90d7b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00l2-2083079000-0968a32b41727ab72dd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0193000000-da94b75048715f96e77fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0002-0910000000-f4855d0bab3b1b8fa113Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udj-0159000000-3b5e183acbd84887fe16Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0193000000-da94b75048715f96e77fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0002-0910000000-f4855d0bab3b1b8fa113Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udj-0159000000-3b5e183acbd84887fe16Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0921000000-ff2132edb15ca1469eefSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0984000000-e2028244f5bef38ea281Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0fmi-0690000000-469ad7488f8e897e6b2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0229000000-a8199e25b519a14a7898Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0349000000-af5335d9f71bb7b4900bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0fk9-0193000000-da94b75048715f96e77fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0002-0910000000-f4855d0bab3b1b8fa113Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-08g0-0190000000-32079ac53e69b8956692Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000b-0090000000-7d9c05a11578bc5a5791Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4r-0290000000-4f5d8d64c096e355566fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0957000000-45912935a7fbe94f54b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-f3c546f2f72d95625bd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0069000000-59d6756b632a0911dd84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4590000000-74b52db35534b4faccd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-8f8cf654c4d87d51c34aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0139000000-baaa885f7a846d9e7e5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-5970000000-bcf1a1d494fa93b47574Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID310
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:15516722 ]
  2. 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 ]
  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. 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. Epub 2006 Jun 27. [PubMed:16806951 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Morin → 6-{[2-(2,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Morin → 6-{[2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Morin → 6-{[2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Morin → 3,4,5-trihydroxy-6-[5-hydroxy-2-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails
Morin → 3,4,5-trihydroxy-6-[3-hydroxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails