Record Information
Version1.0
Creation date2010-04-08 22:06:50 UTC
Update date2019-11-26 03:00:45 UTC
Primary IDFDB005766
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitrinin
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 Number642-15-9
Structure
Thumb
Synonyms
SynonymSource
(-)-Citrininbiospider
Antimycinbiospider
Citriainbiospider
Citrininbiospider
Fintrolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP1.04ALOGPS
logP1.88ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.57 m³·mol⁻¹ChemAxon
Polarizability24.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H14O5
IUPAC name(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione
InChI IdentifierInChI=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 KeyJLWQFKMKUKQXMW-FSPLSTOPSA-N
Isomeric SMILESC[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1C
Average Molecular Weight250.2473
Monoisotopic Molecular Weight250.084123558
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub ClassNot Available
Direct ParentBenzopyrans
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 FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point178.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0090000000-2c1fe13db983b1f6c99fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kai-0490000000-bde2f788648a9c305069Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9610000000-2f7d75f4059482aaf75bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-0090000000-e603034317e276018345Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0390000000-c7d684f9c3624209613fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-4910000000-f674c2dc0f9332acc237Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16765
Pubchem Compound ID219203
Pubchem Substance IDNot Available
ChEBI ID48708
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCITRININ
BIGG IDNot Available
KNApSAcK IDC00029979
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 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 preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).