AFCDB: Cyclokievitone (FDB012215)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:03 UTC

Update date

2019-11-26 03:06:24 UTC

Primary ID

FDB012215

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cyclokievitone

Description

Cyclokievitone belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. Thus, cyclokievitone is considered to be a flavonoid. Cyclokievitone has been detected, but not quantified in, several different foods, such as gram beans (Vigna mungo), green beans (Phaseolus vulgaris), mung beans (Vigna radiata), scarlet beans (Phaseolus coccineus), and common beans (Phaseolus vulgaris). This could make cyclokievitone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyclokievitone.

CAS Number

74175-82-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.63	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.07 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	4	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-hydroxy-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one

InChI Identifier

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

InChI Key

AWLFGFDTGPLHKG-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)OC2=CC(O)=C3C(=O)C(COC3=C2C=C1)C1=CC=C(O)C=C1O

Average Molecular Weight

354.3533

Monoisotopic Molecular Weight

354.110338308

Classification

Description

Belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

8-prenylated isoflavanones

Alternative Parents

Substituents

8-prenylated isoflavanone
Pyranoisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Resorcinol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:4019 )
isoflavanones (C10207 )
Isoflavonoids (C10207 )
Isoflavonoids (LMPK12050493 )

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	355 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cyclokievitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-0918000000-8bb552f798878973f2d4	Spectrum
Predicted GC-MS	Cyclokievitone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pi1-2290450000-7967e00c2405a2f38a88	Spectrum
Predicted GC-MS	Cyclokievitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyclokievitone, 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-0139000000-2959f9c5d663f64ce16e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cki-1779000000-a9888803e31401760c58	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-4930000000-da1c93e03cd7567f2fad	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-da6759113e9aedaf7428	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0359000000-306ce9e150dce00e2e6e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3920000000-68b3f9eab5cc0965d46d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0029000000-3f31991c9a87d69f2c28	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0159000000-b4c4c5293475c699016e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00li-0893000000-2e0d5cc7b7a40f521407	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-b3503695056246b53ddc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0w29-0009000000-03bded540bdc9f31af98	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0900-0169000000-14baaba70a02d09fec7b	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

138019

ChEMBL ID

Not Available

KEGG Compound ID

C10207

Pubchem Compound ID

156777

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33983

CRC / DFC (Dictionary of Food Compounds) ID

HFF37-U:HFF37-U

EAFUS ID

Not Available

Dr. Duke ID

1",2"-DEHYDROCYCLOKIEVITONE|CYCLOKIEVITONE

BIGG ID

Not Available

KNApSAcK ID

C00009558

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
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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Cyclokievitone (FDB012215)

Structure for FDB012215 (Cyclokievitone)