Showing Compound Kaempferide (FDB016499)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:28 UTC

Update date

2025-11-19 01:47:30 UTC

Primary ID

FDB016499

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Kaempferide

Description

Kaempferide 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, kaempferide is considered to be a flavonoid. Kaempferide has been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), european plums (Prunus domestica), grapefruits (Citrus X paradisi), herbs and spices, and sour cherries (Prunus cerasus). This could make kaempferide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Kaempferide.

CAS Number

491-54-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1.3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyrone	ChEBI
4'-O-Methylkaempferol	ChEBI
Campheride	ChEBI
Kaempferol 4'-methyl ether	ChEBI
Kempferide	Kegg
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyrone	HMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
3,5,7-Trihydroxy-4'-methoxy-flavone	HMDB
4'-Methoxy-3,5,7-trihydroxy-flavanone	HMDB
4'-Methoxy-3,5,7-trihydroxyflavone	HMDB
4'-Methylkaempferol	HMDB
5,7-Dihydroxy-4'-methoxyflavonol	HMDB
Kaemferide	HMDB
Kaempferid	HMDB
Kampferide	HMDB
Kampheride	HMDB
3 5 7-Trihydroxy-4'-methoxyflavone	MeSH
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one	biospider
Flavanone, 4'-methoxy-3,5,7-trihydroxy-	biospider
Flavone, 3,5,7-trihydroxy-4'-methoxy-	biospider
Kaempferide	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.36 m³·mol⁻¹	ChemAxon
Polarizability	29.73 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

C16H12O6

IUPAC name

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

InChI Identifier

InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3

InChI Key

SQFSKOYWJBQGKQ-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

Classification

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:6099 )
trihydroxyflavone (CHEBI:6099 )
7-hydroxyflavonol (CHEBI:6099 )
flavonols (C10098 )
Flavones and Flavonols (C10098 )
Flavones and Flavonols (LMPK12110563 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 64.00%; H 4.03%; O 31.97%	DFC
Melting Point	Mp 227-229°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Kaempferide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-0791000000-3624bd10f2d622665fc6	Spectrum
Predicted GC-MS	Kaempferide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fkc-2271950000-26095b3d4aa33777ac68	Spectrum
Predicted GC-MS	Kaempferide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0940000000-563e589b151a0bfb9b74	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001j-0090000000-847e2fc8fc2afde2e8a4	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0091000000-57350f569441ea5d880f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-03fr-0960000000-979796d59b40dcf37939	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0092000000-04e7a3c959e15791ba36	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000t-0290000000-fa97943058aecfae6424	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0lz9-1930000000-02a76c9065a4d7efea34	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000t-1390000000-6bcab21096c8f7188eac	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0090000000-e9170e82b1995679aeb3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001j-0190000000-a2ea43e49a14ecee430e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0pc0-0930000000-7f0eb2e35a23d80bbe81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001j-0090000000-847e2fc8fc2afde2e8a4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-074f2d87992a7d211bc5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0019000000-b776fbc53676f3fbdefc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-6890000000-8ec28b3eec5b952d0820	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-47a5eafa7deb386a7c0a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-2ea66ca52cf34d166887	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f89-3690000000-d8131b75040f06793f22	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

6099

Phenol-Explorer ID

311

DrugBank ID

Not Available

HMDB ID

HMDB37441

CRC / DFC (Dictionary of Food Compounds) ID

KRJ00-L:KRJ00-L

EAFUS ID

Not Available

Dr. Duke ID

KAEMPFERIDE

BIGG ID

Not Available

KNApSAcK ID

C00001060

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

Kaempferide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Aromatase inhibitor	50790	An agent that blocks the activity of aromatase, an enzyme converting androgens to estrogens, reducing estrogen levels. Therapeutically, it's used to treat hormone-sensitive breast cancer, endometriosis, and infertility, by decreasing estrogen-dependent growth and symptoms.	DUKE
Quinone-reductase inducer		An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.	DUKE
Topoisomerase-I inhibitor	50276	An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.	DUKE