Showing Compound Citronetin (FDB005026)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:30 UTC

Update date

2019-11-26 03:00:20 UTC

Primary ID

FDB005026

Secondary Accession Numbers

FDB005027

Chemical Information

FooDB Name

Citronetin

Description

Citronetin is a member of the class of compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, citronetin is considered to be a flavonoid lipid molecule. Citronetin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Citronetin can be found in lemon, which makes citronetin a potential biomarker for the consumption of this food product.

CAS Number

Not Available

Structure

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

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.08 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

C15H12O5

IUPAC name

5,7-dihydroxy-2-(2-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C15H12O5/c16-8-5-11(18)15-12(19)7-13(20-14(15)6-8)9-3-1-2-4-10(9)17/h1-6,13,16-18H,7H2

InChI Key

LSLXUDALHVEMQB-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1O

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

Classification

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140125 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Citronetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-0390000000-3c727aae1e53c8969658	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0390000000-5627ac2d5da22ff5b371	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-1970000000-692ef2cc6fcae4d782d9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-3900000000-0f338f0554d9ee528f7c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-884334a1adb717eab402	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0390000000-f0592ee5023df4d78168	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-8920000000-6cee7968e47208e18ccd	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

LBD51-A:KPP46-T

EAFUS ID

Not Available

Dr. Duke ID

CITRONETIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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).

Showing Compound Citronetin (FDB005026)

Structure for FDB005026 (Citronetin)