Showing Compound Pectolinarigenin (FDB005736)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:49 UTC

Update date

2020-02-24 19:11:07 UTC

Primary ID

FDB005736

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pectolinarigenin

Description

Pectolinarigenin, also known as 5,7-dihydroxy-4',6-dimethoxyflavone or 4'-methylcapillarisin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, pectolinarigenin is considered to be a flavonoid lipid molecule. Pectolinarigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pectolinarigenin can be found in sunflower and tarragon, which makes pectolinarigenin a potential biomarker for the consumption of these food products. Pectolinarigenin is a Cirsium isolate with anti-inflammatory activity and belongs to the flavones .

CAS Number

520-12-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4'-Methylcapillarisin	ChEBI
4'-O-Methylcapillarisin	PhytoBank
4’-O-Methylcapillarisin	PhytoBank
5, 7-Dihydroxy-4',6-dimethoxyflavone	biospider
5,7-Dihydroxy-4',6-dimethoxyflavone	ChEBI
5,7-Dihydroxy-4’,6-dimethoxyflavone	PhytoBank
5,7-Dihydroxy-6, 4'-dimethoxyflavone	biospider
5,7-Dihydroxy-6,4'-dimethoxyflavone	PhytoBank
5,7-Dihydroxy-6,4’-dimethoxyflavone	PhytoBank
5,7-Dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone	biospider

Showing 1 to 10 of 34 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.69	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.1	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.86 m³·mol⁻¹	ChemAxon
Polarizability	31.98 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

C17H14O6

IUPAC name

5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)13-7-11(18)15-14(23-13)8-12(19)17(22-2)16(15)20/h3-8,19-20H,1-2H3

InChI Key

GPQLHGCIAUEJQK-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2O

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

Classification

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:81336 )
dimethoxyflavone (CHEBI:81336 )
Flavones and Flavonols (LMPK12111164 )

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	Not Available
Melting Point	221 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pectolinarigenin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r6-2418900000-df95f0e61458decca87f	Spectrum
Predicted GC-MS	Pectolinarigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ys-0791000000-836fecbd17351b108f80	Spectrum
Predicted GC-MS	Pectolinarigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-920c2c245a2edf3b26fa	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0019000000-cb56dc60015d3d4f40fd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015i-1690000000-15801b75750bca804042	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-23323343b3c8ca9eeb0b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0039000000-4c6fca08a28fa74cfb5e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-2790000000-2eb4853f161600213d16	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-7cd5c53ac9375a349aef	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0093000000-d0a87e3b49bdfd2bf7eb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0769000000-5a9201074b591c58115b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-dfe277d56e0bedec066f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-f257e327df2d3b365338	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0193000000-395b37df907eea9d7b83	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5320438

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

Not Available

EAFUS ID

Not Available

Dr. Duke ID

PECTOLINARIGENIN

BIGG ID

Not Available

KNApSAcK ID

C00003838

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

Sunflower	Expected but not quantified	Not Available	DUKE
Tarragon	Expected but not quantified	Not Available	DUKE

Showing 1 to 2 of 2 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE