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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:19 UTC
Update Date2019-03-29 18:20:55 UTC
HMDB IDHMDB0041857
Secondary Accession Numbers
  • HMDB41857
Metabolite Identification
Common NameCitrinin
DescriptionCitrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are found or used in the production of human foods, such as grain, cheese, sake and red pigments. Citrinin has also been found in commercial red yeast rice supplements, and also in Aspergillus niveus and Aspergillus terreus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).
Structure
Data?1547236918
Synonyms
ValueSource
(3R,4S)-4,6-dihydro-8-Hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acidChEBI
(3R-trans)-4,6-dihydro-8-Hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acidChEBI
(3R,4S)-4,6-dihydro-8-Hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylateGenerator
(3R-trans)-4,6-dihydro-8-Hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylateGenerator
(3R,4S)-8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acidHMDB
AntimycinHMDB
CitriainHMDB
Chemical FormulaC13H14O5
Average Molecular Weight250.2473
Monoisotopic Molecular Weight250.084123558
IUPAC Name(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
Traditional Nameantimycin
CAS Registry Number518-75-2
SMILES
[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C
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/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
InChI KeyCQIUKKVOEOPUDV-IYSWYEEDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP1.23ALOGPS
logP0.81ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.25 m³·mol⁻¹ChemAxon
Polarizability25.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07ii-1950000000-bf6353469eb59dfd035eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3409000000-998272da21093d63d473JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qToF , Positivesplash10-001i-0290000000-19d08795fea7c80d6d85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0290000000-19d08795fea7c80d6d85JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-448b730e55729839783fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-1390000000-b2d7bec5177df13bf6b2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-8c38a7814bc7b5aa2429JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-0090000000-cca6d7a143b768fc5b3dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-4f2f5c7982385791b46fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015j-3910000000-b3cbc912af168ecaeb68JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00029979
Chemspider ID10222475
KEGG Compound IDC16765
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitrinin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48707
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available