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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:06:19 UTC

Update Date

2023-02-21 17:24:08 UTC

HMDB ID

HMDB0034299

Secondary Accession Numbers

HMDB34299

Metabolite Identification

Common Name

Patulin

Description

Patulin 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone	ChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone	ChEBI
4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one	ChEBI
Clavacin	ChEBI
Clavatin	ChEBI
Claviform	ChEBI
Claviformin	ChEBI
Expansin	ChEBI
Expansine	ChEBI
Mycoin C3	ChEBI
Mycoine C3	ChEBI
PAT	ChEBI
Patuline	ChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate, 3,4-lactone	Generator
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate-3,4-lactone	Generator
2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactone	HMDB
2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactone	HMDB
2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactone	HMDB
4-Hydroxy-4,6-dihydrofuro[4,5-c]pyran-2-one	HMDB
4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo(3,3-c)pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 9ci, 8ci	HMDB
Antibiotic SCH 351633	HMDB
Antibiotic ys 1649	HMDB
Clairformin	HMDB
Clavicin	HMDB
Clavitin	HMDB
Expansion	HMDB
Flavicin	HMDB
Gigantic acid?	HMDB
Gigantin	HMDB
Leucopin	HMDB
Mycoin	HMDB
Mycoin c	HMDB
Mycosin	HMDB
Penatin	HMDB
Penicidin	HMDB
SCH 351633	HMDB
Tercinin	HMDB
Terinin	HMDB
YS 1649	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.1201

Monoisotopic Molecular Weight

154.02660868

IUPAC Name

4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one

Traditional Name

patulin

CAS Registry Number

149-29-1

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 Key

ZRWPUFFVAOMMNM-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:74926 )
lactol (CHEBI:74926 )
furopyran (CHEBI:74926 )
Mycotoxins (C16748 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0034299)
Cytoplasm (HMDB: HMDB0034299)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0034299)
Inhalation (HMDB: HMDB0034299)

Enteral

Ingestion (HMDB: HMDB0034299)

Source

Exogenous

Exogenous (HMDB: HMDB0034299)

Food

Food (HMDB: HMDB0034299)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Endogenous

Plant

Plant (HMDB: HMDB0034299)

Fungi

Penicillium (HMDB: HMDB0034299)
Aspergillus clavatus (HMDB: HMDB0034299)
Aspergillus giganteus (HMDB: HMDB0034299)

Process

Not Available

Role

Indirect biological role

Carcinogen (HMDB: HMDB0034299)

Biological role

Carcinogenic agent (HMDB: HMDB0034299)
Mycotoxin (HMDB: HMDB0034299)
Aspergillus metabolite (HMDB: HMDB0034299)
Penicillium metabolite (HMDB: HMDB0034299)
Mutagen (HMDB: HMDB0034299)
Nutrient (HMDB: HMDB0034299)

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antibiotic (HMDB: HMDB0034299)
Antibiotic (HMDB: HMDB0034299)

Environmental role

Environmental contaminant (HMDB: HMDB0034299)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	111 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	163 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.38	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	13.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.476	31661259
DarkChem	[M-H]-	127.49	31661259
DeepCCS	[M-2H]-	162.439	30932474
DeepCCS	[M+Na]+	137.717	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	126.5	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	127.1	32859911
AllCCS	[M+Na-2H]-	127.9	32859911
AllCCS	[M+HCOO]-	128.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.29 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2272 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1217.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	286.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	310.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	438.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	746.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	221.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1046.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	297.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	730.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	274.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	191.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Patulin	OC1OCC=C2OC(=O)C=C12	3085.7	Standard polar	33892256
Patulin	OC1OCC=C2OC(=O)C=C12	1402.0	Standard non polar	33892256
Patulin	OC1OCC=C2OC(=O)C=C12	1539.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Patulin,1TMS,isomer #1	C[Si](C)(C)OC1OCC=C2OC(=O)C=C21	1575.9	Semi standard non polar	33892256
Patulin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OCC=C2OC(=O)C=C21	1832.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Patulin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9700000000-5a48339184b0b8962504	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patulin GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9600000000-3451d632d4f834dc62cc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patulin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patulin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Patulin 10V, Positive-QTOF	splash10-0a4i-0900000000-06be4453ffa97f478a45	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 10V, Positive-QTOF	splash10-0a4i-0900000000-d4bddadeb22df078c3c9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 20V, Positive-QTOF	splash10-0a4i-3900000000-0775e607edc3b24dad13	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 40V, Positive-QTOF	splash10-00di-9100000000-37c4497452b5b85a32f7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 10V, Negative-QTOF	splash10-0udi-0900000000-a5039689c3996db29872	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 20V, Negative-QTOF	splash10-0zfr-1900000000-d8df1f0a351c47943c80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 40V, Negative-QTOF	splash10-06uu-9200000000-cd27858111b7a99f8a9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 10V, Positive-QTOF	splash10-0a4i-0900000000-77b51b14a11efa7e4bd7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 20V, Positive-QTOF	splash10-0a4i-1900000000-f1deb55458afa0cf487a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 40V, Positive-QTOF	splash10-0pbc-9200000000-ec01329ad017386b5211	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 10V, Negative-QTOF	splash10-0udi-0900000000-5328d4e45a2fa398896e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 20V, Negative-QTOF	splash10-1000-3900000000-b2db7ade21b45c80a316	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patulin 40V, Negative-QTOF	splash10-00kf-9200000000-780f5433ebd56a09e203	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Patulin

METLIN ID

Not Available

PubChem Compound

4696

PDB ID

Not Available

ChEBI ID

74926

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1272171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Patulin (HMDB0034299)

MOL for HMDB0034299 (Patulin)

3D MOL for HMDB0034299 (Patulin)

3D SDF for HMDB0034299 (Patulin)

3D-SDF for HMDB0034299 (Patulin)

PDB for HMDB0034299 (Patulin)

3D PDB for HMDB0034299 (Patulin)

SMILES for HMDB0034299 (Patulin)

INCHI for HMDB0034299 (Patulin)

Structure for HMDB0034299 (Patulin)

3D Structure for HMDB0034299 (Patulin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra