Showing Compound Luteone (FDB015507)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:53 UTC

Update date

2019-11-26 03:11:43 UTC

Primary ID

FDB015507

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Luteone

Description

Luteone belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, luteone is considered to be a flavonoid. Luteone has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), lima beans (Phaseolus lunatus), pulses, and white lupines (Lupinus albus). This could make luteone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Luteone.

CAS Number

41743-56-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	ChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
Luteone?	HMDB
Ruizgenin	HMDB, MeSH
Ruizgenin, (3beta,5alpha,6alpha,25R)-isomer	MeSH
Ruizgenin, (3beta,5alpha,6alpha,25S)-isomer	MeSH
5 beta-Spirostane-3 beta,6 alpha-diol	MeSH
Ruizgenin, (3beta,5alpha,6beta,25R)-isomer	MeSH
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI	db_source
Luteone	biospider
Luteone (isoflavone)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.26	ALOGPS
logP	4.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.41	ChemAxon
pKa (Strongest Basic)	-5.2	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	3	ChemAxon
Refractivity	97.91 m³·mol⁻¹	ChemAxon
Polarizability	37.01 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

C20H18O6

IUPAC name

3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3

InChI Key

MMPVAPMCVABQPS-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O

Average Molecular Weight

354.3533

Monoisotopic Molecular Weight

354.110338308

Classification

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:27917 )
isoflavones (C10498 )
Isoflavonoids (C10498 )
Isoflavonoids (LMPK12050287 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Fabaceae

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.79%; H 5.12%; O 27.09%	DFC
Melting Point	Mp 225-227°	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	337 () (MeOH-NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Luteone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-2019000000-e7c452eda2f10db25c9c	Spectrum
Predicted GC-MS	Luteone, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1000039000-76d13aaed8969b7e1f29	Spectrum
Predicted GC-MS	Luteone, 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	splash10-0a4i-0019000000-cb91f2e2808608ed708b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-3159000000-a8c6a86cb19263f22104	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9784000000-01cb188e86ce2e000521	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-9551472e266098511e47	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0339000000-a6058217e23e60cb0aea	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6911000000-38814121556ba6c764d5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-b3503695056246b53ddc	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0019000000-09ce16917cfa9da61560	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2792000000-ec230273cd7094fcda33	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-0e40d1dc69d66b601127	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-f95cd7f394c37bd65111	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-009t-0190000000-062259ae8fdd318edbaf	Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27917

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36595

CRC / DFC (Dictionary of Food Compounds) ID

KCW78-A:KCW78-A

EAFUS ID

Not Available

Dr. Duke ID

LUTEONE

BIGG ID

Not Available

KNApSAcK ID

C00002545

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti feedant			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE