Kaempferol (YMDB01722)

Identification

YMDB ID

YMDB01722

Name

Kaempferol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

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 considered to be a flavonoid. Kaempferol exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Kaempferol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

520-18-3

Weight

Average: 286.2363
Monoisotopic: 286.047738052

InChI Key

IYRMWMYZSQPJKC-UHFFFAOYSA-N

InChI

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

IUPAC Name

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

Traditional IUPAC Name

kaempferol

Chemical Formula

C₁₅H₁₀O₆

SMILES

OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O

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 )

Physical Properties

State

Solid

Charge

Melting point

285-287 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
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	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	FDB000633

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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0079-1963700000-1d3775db7c536f63b70c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0bt9-0000290000-4a7068686e907a319864	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4290000000-ccb984ce16e32c25d878	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0079-1963700000-1d3775db7c536f63b70c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0bt9-0000290000-4a7068686e907a319864	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-0590000000-3bfd778520b9c39bc4ba	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0mc0-2150190000-3a2826fb2ce8460675bc	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)	splash10-000i-0090000000-f0101bac1cb6491794f5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-0690000000-3afcadc746823bc03ebd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0v4i-5900000000-6a870572cf8a486dd6b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positive	splash10-000i-4290000000-75bfe61cc0a42797e86a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-000i-0090000000-ead9f201b8c5b6b6e46e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0190000000-2bc892de84e0225a49cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052u-1930000000-08779ff26cd586d78e41	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udr-0920000000-97d144af795812440c46	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0290000000-5573e7fd91cf25805a11	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014s-2920000000-397e01f2d2cf07025409	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-1920000000-891ca58b63b857f31594	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0079-0090040000-5111d04af3f3d3e053c7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0091000000-295f056c177e6e49fb6b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-0d8eaf63d3860cdc1cbf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-3969010f013a967001da	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-6790000000-5668e7d87a859b519804	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-4cba2efdae1d7d094e17	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-489c309b159fce3df0d6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4950000000-9d8aab7149b59126c14a	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
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	28499
HMDB ID	HMDB05801
Pubchem Compound ID	5280863
Kegg ID	C05903
ChemSpider ID	4444395
FOODB ID	FDB000633
Wikipedia ID	kaempferol
BioCyc ID	Not Available

Structure for #<Compound:0x9c0375b8>