Cannabis Compound Database: Showing Compound Card for Kaempferol (CDB000373)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 26 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:33:39 UTC

Updated at

2022-12-13 19:31:28 UTC

CannabisDB ID

CDB000373

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Kaempferol

Description

Kaempferol, also known as rhamnolutein or c.i. 75640, 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, kaempferol is a flavonoid lipid molecule. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol is a bitter tasting compound. It is very widespread in the plant world and is found in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae and Leguminosae. It is detected in apples, tomatoes, green tea, potatoes, onions, brussels sprouts, squash, cucumbers, lettuce, green beans, peaches, blackberries, raspberries, spinach, grapes, broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon (PMID: 21428901 ). Kaempferol is also one of several flavonoids that are found in cannabis plants (PMID: 6991645 ). Kaempferol is a biomarker for the consumption of dried and cooked beans. Many glycosides of kaempferol, such as kaempferitrin and astragalin, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. Kaempferol has numerous protective properties and has been used to treat intervertebral disc degeneration and colitis, post-menopausal bone loss, acute lung injury and has beneficial effects against cancer, liver injury, obesity and diabetes, and inhibits vascular endothelial inflammation. These treatments and protective properties of kaempferol and the potential mechanisms that kaempferol exerts these effects are part of this review ( PMID: 31572524 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4',5,7-Tetrahydroxyflavone	ChEBI
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4'-trihydroxyflavonol	ChEBI
5,7,4'-Trihydroxyflavonol	ChEBI
C.I. 75640	ChEBI
Campherol	ChEBI
Indigo yellow	ChEBI
Kaempherol	ChEBI
Kampherol	ChEBI
Kempferol	ChEBI
Nimbecetin	ChEBI
Pelargidenolon	ChEBI
Populnetin	ChEBI
Rhamnolutein	ChEBI
Rhamnolutin	ChEBI
Robigenin	ChEBI
Swartziol	ChEBI
Trifolitin	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Kegg
3,4',5,7-Tetrahydroxy-flavone (7ci,8ci)	HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one	HMDB
Kampferol	HMDB
3,4’,5,7-Tetrahydroxyflavone	PhytoBank
3,5,7,4'-Tetrahydroxyflavone	PhytoBank
3,5,7,4’-Tetrahydroxyflavone	PhytoBank
3'-Deoxyquercetin	PhytoBank
3’-Deoxyquercetin	PhytoBank
5,7,4’-Trihydroxyflavonol	PhytoBank
Kaemferol	PhytoBank
Kaempferol	PhytoBank
Kampcetin	PhytoBank
Pelargidenon	PhytoBank

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.24

Monoisotopic Molecular Weight

286.0477

IUPAC Name

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

Traditional Name

kaempferol

CAS Registry Number

520-18-3

SMILES

OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

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

InChI Key

IYRMWMYZSQPJKC-UHFFFAOYSA-N

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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:28499 )
flavonols (CHEBI:28499 )
7-hydroxyflavonol (CHEBI:28499 )
flavonols (C05903 )
Flavones and Flavonols (C05903 )
Flavones and Flavonols (LMPK12110003 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	285 - 287 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.99	ALOGPS
logP	2.46	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.9	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	74.88 m³·mol⁻¹	ChemAxon
Polarizability	27.59 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0079-1963700000-1d3775db7c536f63b70c	Spectrum
GC-MS	Kaempferol, 5 TMS, GC-MS Spectrum	splash10-0bt9-0000290000-4a7068686e907a319864	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-000i-4290000000-ccb984ce16e32c25d878	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0079-1963700000-1d3775db7c536f63b70c	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0bt9-0000290000-4a7068686e907a319864	Spectrum
Predicted GC-MS	Kaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-0590000000-3bfd778520b9c39bc4ba	Spectrum
Predicted GC-MS	Kaempferol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0mc0-2150190000-3a2826fb2ce8460675bc	Spectrum
Predicted GC-MS	Kaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-f0101bac1cb6491794f5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-0690000000-3afcadc746823bc03ebd	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0v4i-5900000000-6a870572cf8a486dd6b7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positive	splash10-000i-4290000000-75bfe61cc0a42797e86a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-000i-0090000000-ead9f201b8c5b6b6e46e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0190000000-2bc892de84e0225a49cf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052u-1930000000-08779ff26cd586d78e41	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udr-0920000000-97d144af795812440c46	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0290000000-5573e7fd91cf25805a11	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014s-2920000000-397e01f2d2cf07025409	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-1920000000-891ca58b63b857f31594	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0079-0090040000-5111d04af3f3d3e053c7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0091000000-295f056c177e6e49fb6b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-0d8eaf63d3860cdc1cbf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-3969010f013a967001da	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-6790000000-5668e7d87a859b519804	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-4cba2efdae1d7d094e17	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-489c309b159fce3df0d6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4950000000-9d8aab7149b59126c14a	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 2 member 10	TAS2R10	12p13	Q9NYW0	details
Taste receptor type 2 member 16	TAS2R16	7q31.1-q31.3\|7q31	Q9NYV7	details
Taste receptor type 2 member 40	TAS2R40	7q34	P59535	details
Taste receptor type 2 member 3	TAS2R3	7q31.3-q32	Q9NYW6	details
Taste receptor type 2 member 4	TAS2R4	7q31.3-q32	Q9NYW5	details
Taste receptor type 2 member 7	TAS2R7	12p13	Q9NYW3	details
Taste receptor type 2 member 9	TAS2R9	12p13	Q9NYW1	details
Taste receptor type 2 member 50	TAS2R50	12p13.2	P59544	details
Taste receptor type 2 member 38	TAS2R38	7q34	P59533	details
Taste receptor type 2 member 31	TAS2R31	12p13.2	P59538	details
Taste receptor type 2 member 1	TAS2R1	5p15.31	Q9NYW7	details
Taste receptor type 2 member 20	TAS2R20	12p13.2	P59543	details
Taste receptor type 2 member 39	TAS2R39	7q34	P59534	details
Taste receptor type 2 member 19	TAS2R19	12p13.2	P59542	details
Taste receptor type 2 member 45	TAS2R45		P59539	details
Taste receptor type 2 member 30	TAS2R30	12p13.2	P59541	details
Taste receptor type 2 member 42	TAS2R42		Q7RTR8	details
Taste receptor type 2 member 41	TAS2R41	7q35	P59536	details
Taste receptor type 2 member 43	TAS2R43	12p13.2	P59537	details
Taste receptor type 2 member 5	TAS2R5	7q34	Q9NYW4	details
Taste receptor type 2 member 46	TAS2R46	12p13.2	P59540	details
Taste receptor type 2 member 13	TAS2R13	12p13.2	Q9NYV9	details
Taste receptor type 2 member 60	TAS2R60	7q35	P59551	details
Taste receptor type 2 member 8	TAS2R8	12p13.2	Q9NYW2	details
Taste receptor type 2 member 14	TAS2R14	12p13.2	Q9NYV8	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.014 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00443 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.00364 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00446 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00459 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.00735 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0005801

DrugBank ID

DB01852

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

kaempferol

METLIN ID

Not Available

PubChem Compound

5280863

PDB ID

KMP

ChEBI ID

28499

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Calderon-Montano JM, Burgos-Moron E, Perez-Guerrero C, Lopez-Lazaro M: A review on the dietary flavonoid kaempferol. Mini Rev Med Chem. 2011 Apr;11(4):298-344. doi: 10.2174/138955711795305335. [PubMed:21428901 ]
Ren J, Lu Y, Qian Y, Chen B, Wu T, Ji G: Recent progress regarding kaempferol for the treatment of various diseases. Exp Ther Med. 2019 Oct;18(4):2759-2776. doi: 10.3892/etm.2019.7886. Epub 2019 Aug 13. [PubMed:31572524 ]

Only showing the first 10 proteins. There are 26 proteins in total.

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Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Only showing the first 10 proteins. There are 26 proteins in total.

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Showing Compound Card for Kaempferol (CDB000373)

Structure for CDB000373 (Kaempferol)

Enzymes