Details of the Drug

General Information of Drug (ID: DMN7S4L)

• Drug Name: OXYRESVERATROL
• Synonyms: Oxyresveratrol; 29700-22-9; Tetrahydroxystilbene; (E)-4-(3,5-Dihydroxystyryl)benzene-1,3-diol; UNII-6V071CP5CR; trans-oxyresveratrol; 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; OXYLRESVERATROL; 4721-07-7; 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; CHEMBL43065; CHEBI:7870; 6V071CP5CR; 2,3',4,5'-Tetrahydroxystilbene; AK158555; 4-(3,5-Dihydroxystyryl)benzene-1,3-diol; J-501984; 4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,3-diol; 1,3-Benzenediol, 4-[(1E)-2-(3,5-dihydroxyphenyl)ethenyl]-; Puag-haad

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); 244.24
  Logarithm of the Partition Coefficient (xlogp); 2.8
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 4
  Hydrogen Bond Acceptor Count (hbondacc); 4
• Chemical Identifiers:
  Formula: C14H12O4
  IUPAC Name: 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
  Canonical SMILES: C1=CC(=C(C=C1O)O)/C=C/C2=CC(=CC(=C2)O)O
  InChI: InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+
  InChIKey: PDHAOJSHSJQANO-OWOJBTEDSA-N
• Cross-matching ID:
  PubChem CID: 5281717
  ChEBI ID: CHEBI:7870
  CAS Number: 29700-22-9
  TTD ID: D06ZRX

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Tyrosinase (TYR)	TTULVH8	TYRO_HUMAN	Inhibitor	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Acetyl-CoA carboxylase 1 (ACACA)	OT5CQPZY	ACACA_HUMAN	Post-Translational Modifications	[2]
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[3]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A)	OTI862QH	CPT1A_HUMAN	Gene/Protein Processing	[2]
Claudin-1 (CLDN1)	OT27KV99	CLD1_HUMAN	Gene/Protein Processing	[4]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[6]
Cytochrome P450 2C8 (CYP2C8)	OTHCWT42	CP2C8_HUMAN	Gene/Protein Processing	[6]
Glutamate--cysteine ligase catalytic subunit (GCLC)	OTESDI4D	GSH1_HUMAN	Gene/Protein Processing	[7]
Glutamine-dependent NAD(+) synthetase (NADSYN1)	OTD5FS4Q	NADE_HUMAN	Gene/Protein Processing	[8]
Glutathione S-transferase A2 (GSTA2)	OTW7UB1H	GSTA2_HUMAN	Gene/Protein Processing	[7]

Molecular Expression Atlas of This Drug

• The Studied Disease: Discovery agent
• ICD Disease Classification: N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Tyrosinase (TYR)	DTT	TYR	6.68E-04	2.54	1.15

References

• [1] Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5650-3.
• [2] Oxyresveratrol ameliorates nonalcoholic fatty liver disease by regulating hepatic lipogenesis and fatty acid oxidation through liver kinase B1 and AMP-activated protein kinase. Chem Biol Interact. 2018 Jun 1;289:68-74. doi: 10.1016/j.cbi.2018.04.023. Epub 2018 Apr 24.
• [3] Hydroxystilbenes and methoxystilbenes activate human aryl hydrocarbon receptor and induce CYP1A genes in human hepatoma cells and human hepatocytes. Food Chem Toxicol. 2017 May;103:122-132.
• [4] Oxyresveratrol improves tight junction integrity through the PKC and MAPK signaling pathways in Caco-2?cells. Food Chem Toxicol. 2017 Oct;108(Pt A):203-213. doi: 10.1016/j.fct.2017.08.002. Epub 2017 Aug 2.
• [5] Anti-tumor properties of methoxylated analogues of resveratrol in malignant MCF-7 but not in non-tumorigenic MCF-10A mammary epithelial cell lines. Toxicology. 2019 Jun 15;422:35-43.
• [6] Trans-resveratrol, but not other natural stilbenes occurring in food, carries the risk of drug-food interaction via inhibition of cytochrome P450 enzymes or interaction with xenosensor receptors. Toxicol Lett. 2019 Jan;300:81-91.
• [7] Oxyresveratrol abrogates oxidative stress by activating ERK-Nrf2 pathway in the liver. Chem Biol Interact. 2016 Feb 5;245:110-21.
• [8] Oxyresveratrol stimulates mucin production in an NAD+-dependent manner in human intestinal goblet cells. Food Chem Toxicol. 2018 Aug;118:880-888.