Details of the Drug

General Information of Drug (ID: DM6USPC)

Drug Name

TRISMETHOXYRESVERATROL

Synonyms

22255-22-7; trans-Trimethoxyresveratrol; (E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene; (E)-3,5,4'-Trimethoxystilbene; 3,4',5-trimethoxy-trans-stilbene; 3,4',5-trimethoxystilbene; 3,5,4'-trimethoxystilbene; TRIMETHOXYSTILBENE; TRISMETHOXYRESVERATROL; E-Resveratrol trimethyl ether; CHEMBL296411; 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene; trans-3,4',5-trimethoxystilbene; GDHNBPHYVRHYCC-SNAWJCMRSA-N; (E)-3,4',5-Trimethoxystilbene; 5-[2-(4-Methoxyphenyl)Ethenyl]-1,3-Dimethoxy Benzene

Indication

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

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

270.32

Logarithm of the Partition Coefficient (xlogp)

4.1

Rotatable Bond Count (rotbonds)

5

Hydrogen Bond Donor Count (hbonddonor)

0

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C17H18O3
IUPAC Name: 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
Canonical SMILES: COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)OC)OC
InChI: InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+
InChIKey: GDHNBPHYVRHYCC-SNAWJCMRSA-N

Cross-matching ID

PubChem CID: 5388063
CAS Number: 22255-22-7
TTD ID: D0O9NE

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cytochrome P450 1B1 (CYP1B1)	TTI84H7	CP1B1_HUMAN	Inhibitor	[1]
Multidrug resistance protein 1 (ABCB1)	TT3OT40	MDR1_HUMAN	Inhibitor	[2]
Tyrosine-protein kinase ABL1 (ABL)	TT3PJMV	ABL1_HUMAN	Inhibitor	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[3]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Protein Interaction/Cellular Processes	[4]
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[5]
Cadherin-1 (CDH1)	OTFJMXPM	CADH1_HUMAN	Gene/Protein Processing	[6]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Post-Translational Modifications	[6]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[5]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[6]
Myc proto-oncogene protein (MYC)	OTPV5LUK	MYC_HUMAN	Gene/Protein Processing	[6]
Protein c-Fos (FOS)	OTJBUVWS	FOS_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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
Multidrug resistance protein 1 (ABCB1)	DTT	ABCB1	3.12E-33	-0.83	-1.04

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J Med Chem. 2002 Jan 3;45(1):160-4.
2	Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells. J Med Chem. 2006 May 18;49(10):3012-8.
3	Resveratrol analog-3,5,4'-trimethoxy-trans-stilbene inhibits invasion of human lung adenocarcinoma cells by suppressing the MAPK pathway and decreasing matrix metalloproteinase-2 expression. Mol Nutr Food Res. 2009 Mar;53(3):407-16. doi: 10.1002/mnfr.200800123.
4	Resveratrol promotes clearance of Alzheimer's disease amyloid-beta peptides. J Biol Chem. 2005 Nov 11;280(45):37377-82.
5	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.
6	3,5,4'-Trimethoxystilbene, a natural methoxylated analog of resveratrol, inhibits breast cancer cell invasiveness by downregulation of PI3K/Akt and Wnt/-catenin signaling cascades and reversal of epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2013 Nov 1;272(3):746-56. doi: 10.1016/j.taap.2013.07.019. Epub 2013 Aug 3.