ContaminantDB: Limocitrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 20:55:28 UTC

Update Date

2016-11-09 01:17:40 UTC

Accession Number

CHEM023242

Identification

Common Name

Limocitrin

Class

Small Molecule

Description

Limocitrin is found in citrus. Limocitrin is a constituent of citrus fruit peels

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
4',5,7-Trihydroxy-3',8-dimethoxyflavonol	HMDB
Gossypetin 3',8-dimethyl ether	HMDB
Sedoflorigenin	HMDB

Chemical Formula

C₁₇H₁₄O₈

Average Molecular Mass

346.288 g/mol

Monoisotopic Mass

346.069 g/mol

CAS Registry Number

489-33-8

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-chromen-4-one

Traditional Name

limocitrin

SMILES

COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O

InChI Identifier

InChI=1S/C17H14O8/c1-23-11-5-7(3-4-8(11)18)15-14(22)13(21)12-9(19)6-10(20)16(24-2)17(12)25-15/h3-6,18-20,22H,1-2H3

InChI Key

IBXCKSUZOFKGSB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3p-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113241 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.81 m³·mol⁻¹	ChemAxon
Polarizability	33.26 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0319000000-916e78a0249246554fa6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-01b9-2312089000-167f74930f837df18f1f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0009000000-68df39c49592dae61826	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0009000000-92129baf970b23db0539	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03y3-0950000000-b6df732dc8a613daa6f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0009000000-095643a6e479babccf52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000t-0009000000-f1352a438263d2a9a892	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-080474eeeaacd09b4a87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-84db9ce8c659ba58f203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0009000000-f1352a438263d2a9a892	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-095643a6e479babccf52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03y3-0950000000-b6df732dc8a613daa6f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-f4088022d7a1ce5904d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-072cbfd0f75bab2c8282	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-1952000000-c8c1fc3ae74487ec1567	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-e4f48dc3b9efce5f0790	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0029000000-4b7f4346f71d27eecb9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01bc-2982000000-a396d10514a1787c57c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-24b80c82c41a998b9ea5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-b4bb1ffb9bc021542b41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ls-1903000000-cefe5a930f54d156cf12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-4173ab4cf400ed4c2037	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0439000000-90b8a03523c50fc7a178	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00yi-1921000000-ecebb4a8ac8569f176c3	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029516

FooDB ID

FDB000652

Phenol Explorer ID

Not Available

KNApSAcK ID

C00004731

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4590163

ChEBI ID

542813

PubChem Compound ID

5489485

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Limocitrin (CHEM023242)

Structure for CHEM023242: Limocitrin