Details of the Drug

General Information of Drug (ID: DM0RV9C)

• Drug Name: PATULIN
• Synonyms: patulin; Expansin; Clavacin; Expansine; Patuline; Claviform; Clavatin; 149-29-1; Clairformin; Claviformin; Leucopin; Gigantin; Tercinin; Mycoin; Mycoine C3; Mycoin C3; Penicidin; Penatin; Mycosin; Terinin; Mycoin C; 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one; Sch-351633; NSC 8120; NSC 32951; 4-Hydroxy-4H-furo(3,2-C)pyran-2(6H)-one; CCRIS 4940; (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone; HSDB 3522; 4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one; NSC8120; NSC32951; EINECS 205-735-2; 4H-Furo[3,2-c]pyran-2(6H)-one, 4-hydroxy-

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 154.12
  Logarithm of the Partition Coefficient (xlogp); -1
  Rotatable Bond Count (rotbonds); 0
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 4
• Chemical Identifiers:
  Formula: C7H6O4
  IUPAC Name: 4-hydroxy-4,6-dihydrofuro[3,2-c]pyran-2-one
  Canonical SMILES: C1C=C2C(=CC(=O)O2)C(O1)O
  InChI: InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
  InChIKey: ZRWPUFFVAOMMNM-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 4696
  ChEBI ID: CHEBI:74926
  CAS Number: 149-29-1
  DrugBank ID: DB15586
  TTD ID: D0LB4A

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Hepatitis C virus NS3 helicase (HCV NS3)	TTWXB3E	POLG_HCV1	Inhibitor	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bcl-2-like protein 11 (BCL2L11)	OTNQQWFJ	B2L11_HUMAN	Gene/Protein Processing	[2]
Beclin-1 (BECN1)	OT4X293M	BECN1_HUMAN	Post-Translational Modifications	[3]
BH3-interacting domain death agonist (BID)	OTOSHSHU	BID_HUMAN	Gene/Protein Processing	[2]
Caspase-1 (CASP1)	OTZ3YQFU	CASP1_HUMAN	Gene/Protein Processing	[4]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[6]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[6]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Drug Response	[7]
Cathepsin B (CTSB)	OTP9G5QB	CATB_HUMAN	Protein Interaction/Cellular Processes	[4]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[8]

References

• [1] Control of hepatitis C: a medicinal chemistry perspective. J Med Chem. 2005 Jan 13;48(1):1-20.
• [2] Complementary cell-based high-throughput screens identify novel modulators of the unfolded protein response. J Biomol Screen. 2011 Sep;16(8):825-35. doi: 10.1177/1087057111414893. Epub 2011 Aug 15.
• [3] Patulin disrupts SLC7A11-cystine-cysteine-GSH antioxidant system and promotes renal cell ferroptosis both in vitro and in vivo. Food Chem Toxicol. 2022 Aug;166:113255. doi: 10.1016/j.fct.2022.113255. Epub 2022 Jun 27.
• [4] Patulin induces pyroptosis through the autophagic-inflammasomal pathway in liver. Food Chem Toxicol. 2021 Jan;147:111867. doi: 10.1016/j.fct.2020.111867. Epub 2020 Nov 17.
• [5] Patulin induces apoptosis through ROS-mediated endoplasmic reticulum stress pathway. Toxicol Sci. 2015 Apr;144(2):328-37. doi: 10.1093/toxsci/kfu319. Epub 2015 Jan 9.
• [6] Involvement of NADPH oxidase in patulin-induced oxidative damage and cytotoxicity in HEK293?cells. Food Chem Toxicol. 2021 Apr;150:112055. doi: 10.1016/j.fct.2021.112055. Epub 2021 Feb 9.
• [7] Induction of oxidative stress response by the mycotoxin patulin in mammalian cells. Toxicol Sci. 2007 Feb;95(2):340-7. doi: 10.1093/toxsci/kfl156. Epub 2006 Nov 7.
• [8] Patulin-induced oxidative DNA damage and p53 modulation in HepG2 cells. Toxicon. 2010 Feb-Mar;55(2-3):390-5. doi: 10.1016/j.toxicon.2009.08.019. Epub 2009 Sep 8.