Quercetin (YMDB01777)

Identification

YMDB ID

YMDB01777

Name

Quercetin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Quercetin, also known as sophoretin or xanthaurine, 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, quercetin is considered to be a flavonoid. Quercetin exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Quercetin.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Quercetol
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
3,3',4',5,7-Pentahydroxyflavone
3,5,7,3',4'-Pentahydroxyflavone
Sophoretin
Xanthaurine
3,3',4,5,7-Pentahydroxyflavone
Dikvertin
2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one
3',4',5,7-Tetrahydroxyflavan-3-ol
3',4',5,7-Tetrahydroxyflavon-3-ol
3,4',5,5',7-Pentahydroxy-flavone
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ON
Flavin meletin
Meletin
Quercetin dihydrate
Quertin
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one
3,3’,4’,5,7-Pentahydroxyflavone
3,5,7,3’,4’-Pentahydroxyflavone
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one
3'-Hydroxykaempferol
3’-Hydroxykaempferol
Quercetine
Quertine

CAS number

117-39-5

Weight

Average: 302.2357
Monoisotopic: 302.042652674

InChI Key

REFJWTPEDVJJIY-UHFFFAOYSA-N

InChI

InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

Traditional IUPAC Name

quercetin

Chemical Formula

C₁₅H₁₀O₇

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentahydroxyflavone (CHEBI:16243 )
7-hydroxyflavonol (CHEBI:16243 )
flavonols (C00389 )
Flavones and Flavonols (C00389 )
Flavones and Flavonols (LMPK12110004 )

Physical Properties

State

Solid

Charge

Melting point

316-318 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.06 mg/mL at 16 oC [SEIDELL,A (1941)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	1.81	ALOGPS
logP	2.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.86 m³·mol⁻¹	ChemAxon
Polarizability	28.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB011904

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0bt9-2611390000-f8e98c928a7ed82acda4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0bt9-2611390000-f8e98c928a7ed82acda4	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-0591000000-2a146657da898ec9322e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-00l2-2093078000-1de46637305246feffd2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0009000000-d4689b76f41c73487399	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0967000000-613e61ec0c69ed0ee630	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0uy0-5910000000-ee816015eec26c8621b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-0udi-0009000000-ec1cab852ed9f9f78fa4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-1907000000-6f36df2733dadae380c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0309000000-976a99c106ceca16d73b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0pi0-1900000000-b2e286366d41e47dd8fc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0209000000-e891863ec110aeb660b0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0940000000-aa52db00c1defe3ccf75	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0219000000-5ef285c4b6bfd220b8b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0219000000-547c83bb70e7da007d6c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-1907000000-a59602c09f66e9656068	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-0udi-0009000000-4416f39adf6c9b919bfa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0udi-0019000000-eb14ec62fc2fb2f1da88	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0ufr-0910000000-0730bca525c17aac75c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0030290000-06238e4a98a4daad3265	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0039008002-9df3edfb34deb15f8474	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0039008002-9df3edfb34deb15f8474	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0uka-0193000000-3325ca1a080730a9c0bf	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-ee8570ac70818e8939bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0279000000-71b5db7ef8322cc8b9e9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-7960000000-7edbb229853a642749ac	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-21580b9d8394d2eea3a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0239000000-b77fcb9c0ce11dc515bf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0apr-5940000000-0590bdee504c5ed6ba36	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16243
HMDB ID	HMDB05794
Pubchem Compound ID	22339062
Kegg ID	C00389
ChemSpider ID	4444051
FOODB ID	FDB011904
Wikipedia ID	Quercetin
BioCyc ID	Not Available

Structure for #<Compound:0xab92d370>