Showing Compound Luteolin 7-disulfoglucoside (FDB018235)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:35 UTC

Update date

2019-11-26 03:15:54 UTC

Primary ID

FDB018235

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Luteolin 7-disulfoglucoside

Description

Luteolin, also known as digitoflavone or flacitran, 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). Thus, luteolin is considered to be a flavonoid. Luteolin is a bitter tasting compound. Luteolin is found, on average, in the highest concentration within a few different foods, such as common oreganos (Origanum vulgare), wild celeries (Apium graveolens), and anises (Pimpinella anisum) and in a lower concentration in spinaches (Spinacia oleracea), celery leaves (Apium graveolens var. secalinum), and italian oreganos (Origanum X majoricum). Luteolin has also been detected, but not quantified in, several different foods, such as figs (Ficus carica), java plums (Syzygium cumini), winged beans (Psophocarpus tetragonolobus), alpine sweetvetches (Hedysarum alpinum), and white mustards (Sinapis alba). This could make luteolin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Luteolin.

CAS Number

121283-87-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one	PhytoBank
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one	HMDB
3',4',5,7-Tetrahydroxy-flavone	MeSH, HMDB
3',4',5,7-Tetrahydroxyflavone	ChEBI
3',4',5,7-Tetrahydroxyflavone 7-O-(disulfoglucoside)	manual
3’,4’,5,7-Tetrahydroxyflavone	PhytoBank
5,7,3',4'-Tetrahydroxyflavone	ChEBI

Showing 1 to 10 of 19 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.89 m³·mol⁻¹	ChemAxon
Polarizability	27.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O6

IUPAC name

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

InChI Identifier

InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H

InChI Key

IQPNAANSBPBGFQ-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

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).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:15864 )
3'-hydroxyflavonoid (CHEBI:15864 )
flavones (C01514 )
Flavones and Flavonols (C01514 )
Flavones and Flavonols (LMPK12110006 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 41.45%; H 3.31%; O 44.70%; S 10.54%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Luteolin, 4 TMS, GC-MS Spectrum	splash10-0bt9-0000190000-f355e064b0e4a8fee2a8	Spectrum
GC-MS	Luteolin, non-derivatized, GC-MS Spectrum	splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e	Spectrum
GC-MS	Luteolin, non-derivatized, GC-MS Spectrum	splash10-0bt9-0000190000-f355e064b0e4a8fee2a8	Spectrum
GC-MS	Luteolin, non-derivatized, GC-MS Spectrum	splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e	Spectrum
GC-MS	Luteolin, non-derivatized, GC-MS Spectrum	splash10-00dj-1735900000-66504e5cc81bcf3dd0a2	Spectrum
Predicted GC-MS	Luteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aou-0290000000-c72aa0a44afb34434ad5	Spectrum
Predicted GC-MS	Luteolin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zmi-2040190000-5d0acf5ba2153f12546d	Spectrum
Predicted GC-MS	Luteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Luteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0490000000-b23f87f7af1af38d9686	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0690000000-74dbeef56be77f266f6e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-001i-0900000000-4b5589ca157de0b5885b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0079-0090080000-787383a28d957fc65a9e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-03ffb3e4764e7236f82d	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0190000000-7f42ffe76ed9c3f69f11	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-03ffb3e4764e7236f82d	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0190000000-7f42ffe76ed9c3f69f11	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-000i-0790000000-814cdaf9d50189cf2f2a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0490000000-b23f87f7af1af38d9686	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0690000000-4135ff68dafc65e9f339	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-4b5589ca157de0b5885b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0090000000-568d5c1e3df3c5693fb4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0190000000-b20ef421e6accd0523a4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-2ca1121832520dd96a2c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0490000000-14b50e413340dc95fac3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0490000000-371552bb5776fd662dd9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0590000000-a412d0980f838bf49619	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0090000000-075f1c69f8e77ea5dbe9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0190000000-7f42ffe76ed9c3f69f11	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-236ab0853a3df459fc37	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0900000000-fda1f09c1506187911ff	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-956ceb8d223bd9454f93	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1900000000-ba91f3571fdd8398c5e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-001i-0900000000-051f4eceea0c40ddb177	2021-09-20	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HQG45-Z:LHR65-P

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Luteolin 7-disulfoglucoside (FDB018235)

Structure for FDB018235 (Luteolin 7-disulfoglucoside)