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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:06:19 UTC
Update Date2019-07-23 06:15:42 UTC
HMDB IDHMDB0034299
Secondary Accession Numbers
  • HMDB34299
Metabolite Identification
Common NamePatulin
DescriptionPatulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice
Structure
Data?1563862542
Synonyms
ValueSource
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactoneChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactoneChEBI
4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-oneChEBI
ClavacinChEBI
ClavatinChEBI
ClaviformChEBI
ClaviforminChEBI
ExpansinChEBI
ExpansineChEBI
Mycoin C3ChEBI
Mycoine C3ChEBI
PATChEBI
PatulineChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate, 3,4-lactoneGenerator
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate-3,4-lactoneGenerator
2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactoneHMDB
2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactoneHMDB
2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactoneHMDB
4-Hydroxy-4,6-dihydrofuro[4,5-c]pyran-2-oneHMDB
4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-oneHMDB
4-Hydroxy-4H-furo(3,3-c)pyran-2(6H)-oneHMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-oneHMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 9ci, 8ciHMDB
Antibiotic SCH 351633HMDB
Antibiotic ys 1649HMDB
ClairforminHMDB
ClavicinHMDB
ClavitinHMDB
ExpansionHMDB
FlavicinHMDB
Gigantic acid?HMDB
GigantinHMDB
LeucopinHMDB
MycoinHMDB
Mycoin cHMDB
MycosinHMDB
PenatinHMDB
PenicidinHMDB
SCH 351633HMDB
TercininHMDB
TerininHMDB
YS 1649HMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.1201
Monoisotopic Molecular Weight154.02660868
IUPAC Name4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one
Traditional Namepatulin
CAS Registry Number149-29-1
SMILES
OC1OCC=C2OC(=O)C=C12
InChI Identifier
InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
InChI KeyZRWPUFFVAOMMNM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassNot Available
Direct ParentPyrans
Alternative Parents
Substituents
  • 2-furanone
  • Pyran
  • Dihydrofuran
  • Enol ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Indirect biological role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility163 g/LALOGPS
logP-0.27ALOGPS
logP-0.38ChemAxon
logS0.02ALOGPS
pKa (Strongest Acidic)11.65ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.03 m³·mol⁻¹ChemAxon
Polarizability13.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9700000000-5a48339184b0b8962504Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9600000000-3451d632d4f834dc62ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d4bddadeb22df078c3c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3900000000-0775e607edc3b24dad13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-37c4497452b5b85a32f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a5039689c3996db29872Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1900000000-d8df1f0a351c47943c80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06uu-9200000000-cd27858111b7a99f8a9aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB012642
KNApSAcK IDC00024000
Chemspider ID4534
KEGG Compound IDC16748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPatulin
METLIN IDNot Available
PubChem Compound4696
PDB IDNot Available
ChEBI ID74926
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ozsoy N, Selmanoglu G, Kockaya EA, Gul N, Cebesoy S: Effect of patulin on the interdigitating dendritic cells (IDCs) of rat thymus. Cell Biochem Funct. 2008 Mar-Apr;26(2):192-6. [PubMed:17702051 ]
  2. McKinley ER, Carlton WW, Boon GD: Patulin mycotoxicosis in the rat: toxicology, pathology and clinical pathology. Food Chem Toxicol. 1982 Jun;20(3):289-300. [PubMed:7201955 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .