AFCDB: Citrinin (FDB005766)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:50 UTC

Update date

2019-11-26 03:00:45 UTC

Primary ID

FDB005766

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Citrinin

Description

Citrinin is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Citrinin can be found in barley and common wheat, which makes citrinin a potential biomarker for the consumption of these food products. Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminate long-stored food and it causes different toxic effects, like nephrotoxic, hepatotoxic and cytotoxic effects. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products .

CAS Number

642-15-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.96 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.57 m³·mol⁻¹	ChemAxon
Polarizability	24.53 Å³	ChemAxon
Number of Rings	2	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

C13H14O5

IUPAC name

(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione

InChI Identifier

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1

InChI Key

JLWQFKMKUKQXMW-FSPLSTOPSA-N

Isomeric SMILES

C[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1C

Average Molecular Weight

250.2473

Monoisotopic Molecular Weight

250.084123558

Classification

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
O-quinomethane
Quinomethane
Cyclohexenone
Vinylogous acid
Vinylogous ester
Ketene acetal or derivatives
Ketone
Cyclic ketone
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	178.5 oC
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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0090000000-2c1fe13db983b1f6c99f	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kai-0490000000-bde2f788648a9c305069	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9610000000-2f7d75f4059482aaf75b	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-0090000000-e603034317e276018345	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0390000000-c7d684f9c3624209613f	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002o-4910000000-f674c2dc0f9332acc237	2019-02-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C16765

Pubchem Compound ID

219203

Pubchem Substance ID

Not Available

ChEBI ID

48708

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CITRININ

BIGG ID

Not Available

KNApSAcK ID

C00029979

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
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	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).

Citrinin (FDB005766)

Structure for FDB005766 (Citrinin)