ChemFOnt: Showing chemical card for Citronin (CFc000333727)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:14:06 UTC

Chemfont ID

CFc000333727

Molecule Identification

Common Name

Citronin

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

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

Chemical Taxonomy

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 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)

Process

Not Available

Role

Not Available

Physical Properties

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

External Links

HMDB ID

HMDB0150646

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005026

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

179999

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Citronin (CFc000333727)

MOL for CFc000333727 (Citronin)

3D MOL for CFc000333727 (Citronin)

3D SDF for CFc000333727 (Citronin)

3D-SDF for CFc000333727 (Citronin)

PDB for CFc000333727 (Citronin)

3D PDB for CFc000333727 (Citronin)

SMILES for CFc000333727 (Citronin)

INCHI for CFc000333727 (Citronin)

Structure for CFc000333727 (Citronin)

3D Structure for CFc000333727 (Citronin)