Showing Compound Licoisoflavone A (FDB012398)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2019-11-26 03:06:42 UTC

Primary ID

FDB012398

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Licoisoflavone A

Description

Licoisoflavone A, also known as phaseoluteone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, licoisoflavone a is considered to be a flavonoid. Licoisoflavone A has been detected, but not quantified in, several different foods, such as green beans (Phaseolus vulgaris), common beans (Phaseolus vulgaris), corns (Zea mays), white lupines (Lupinus albus), and oats (Avena sativa). This could make licoisoflavone a a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Licoisoflavone A.

CAS Number

66056-19-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2',4',5,7-Tetrahydroxy-3'-(3,3-dimethylallyl)isoflavone	ChEBI
Phaseoluteone	ChEBI
3'-Isopentenyl-2',4',5,7-tetrahydroxyisoflavone	HMDB
Licoisoflavone	HMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ci	HMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one	db_source
Licoisoflavone A	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.29	ALOGPS
logP	4.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-5.3	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	36.83 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-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one

InChI Identifier

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

InChI Key

KCUZCRLRQVRBBV-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O

Average Molecular Weight

354.358

Monoisotopic Molecular Weight

354.1103383

Classification

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28620 )
isoflavones (C10486 )
Isoflavonoids (C10486 )
Isoflavonoids (LMPK12050286 )

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	Not Available
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	Licoisoflavone A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004u-2019000000-2f739f3452171f905be2	Spectrum
Predicted GC-MS	Licoisoflavone A, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1000049000-7018f194d1008ff5433d	Spectrum
Predicted GC-MS	Licoisoflavone A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Licoisoflavone A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0259000000-495f77efc5f1a3a3f53e	Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4j-0379000000-8433cfe87c1ae275bcd4	Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-0udi-0229000000-359d0281bb2960df18ab	Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4j-0379000000-164d4415475e4af9dc35	Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0259000000-0aaedb95807e7419c45e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-62f92498db843c9e5858	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ot-3349000000-ed8805f32a0bbcd8f235	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gba-8952000000-6c41fa9ae3eca464c67b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0109000000-be91e8e91b4067f6ed22	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0918000000-fb711c0f7e6d3a6949fe	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pki-2921000000-ec8a5e470e5efab9b710	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	splash10-0002-0090000000-64cb783d19451782d0e7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-0191000000-f709c80b15ac681aff91	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-0029000000-4100593e7262216dd627	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0n4u-2394000000-819b2b3d4c43b4896111	Spectrum

NMR

Not Available

External Links

ChemSpider ID

4445102

ChEMBL ID

Not Available

KEGG Compound ID

C10486

Pubchem Compound ID

5281789

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34125

CRC / DFC (Dictionary of Food Compounds) ID

HGS69-Z:HGS69-Z

EAFUS ID

Not Available

Dr. Duke ID

LICOISOFLAVONE-A|PHASEOLUTEONE

BIGG ID

Not Available

KNApSAcK ID

C00002542

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