Back to Compounds

Showing Compound Scutellarein (FDB002464)

Record Information
Version1.0
Creation date2010-04-08 22:05:23 UTC
Update date2025-11-18 22:37:38 UTC
Primary IDFDB002464
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameScutellarein
DescriptionScutellarein, also known as 6-hydroxyapigenin or 4',5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4',6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4',5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri .
CAS Number529-53-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4',5,6,7-TetrahydroxyflavanoneChEBI
5,6,7,4'-TetrahydroxyflavoneChEBI
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
6-HydroxyapigeninChEBI
IsocarthamidinChEBI
4',5,6,7-Tetrahydroxy-flavanoneMeSH
6-Hydroxy-apigeninMeSH
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Scutellareindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.74ALOGPS
logP2.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.75ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.89 m³·mol⁻¹ChemAxon
Polarizability27.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O6
IUPAC name5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)11-5-9(17)13-12(21-11)6-10(18)14(19)15(13)20/h1-6,16,18-20H
InChI KeyJVXZRQGOGOXCEC-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(O)=C2O
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
Classification
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.94%; H 3.52%; O 33.54%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSScutellarein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-0590000000-6c902a6905382235d4e0Spectrum
Predicted GC-MSScutellarein, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0l6r-3304190000-ed90b0d8e1697e6ad54cSpectrum
Predicted GC-MSScutellarein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0w29-0119005000-c793e997a188821d0f592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00kr-0950000000-2a9ad8450a74a9138db72017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 6V, Negativesplash10-00kr-0950000000-2a9ad8450a74a9138db72017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0090000000-dfb81d7bffac0efa5dd22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-dfb81d7bffac0efa5dd22017-08-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8d7ea4f4ec2d7b4f1d142016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-7b9d9b850e6da6eeeafb2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02or-3950000000-f9ad546407391419e2382016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4ac71ddb7e307709dad62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-0c95eb49eb0318e4b5262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-3930000000-5c4e473404a9305998092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0950000000-f2da8d2ba51c443ce9b72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-63d7761084cd6181cdc12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-2bf60c631a3f6dfd69852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-0920000000-798fafdb28974a2136532021-09-22View Spectrum
NMRNot Available
ChemSpider ID4445014
ChEMBL IDCHEMBL55415
KEGG Compound IDC10184
Pubchem Compound ID5281697
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID280
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCLX81-C:CLX81-C
EAFUS IDNot Available
Dr. Duke IDSCUTELLAREIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDScutellarein
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti-hemolytic50248 An agent that prevents or reduces the breakdown of red blood cells, used to treat conditions such as hemolytic anemia, and other disorders where red blood cell destruction occurs, promoting healthy red blood cell count and preventing related complications.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Phospholipase-A2 inhibitor50469 An agent that blocks the activity of phospholipase A2, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like acute pancreatitis, sepsis, and inflammatory disorders, by inhibiting the production of pro-inflammatory mediators.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.