Details of the Drug

General Information of Drug (ID: DMYXI2V)

Drug Name
(E)-4-(3,5-dimethoxystyryl)phenol
Synonyms
Pterostilbene; 537-42-8; 4-(3,5-Dimethoxystyryl)phenol; 3',5'-Dimethoxy-4-stilbenol; trans-pterostilbene; 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol; pterostilben; 4-[(E)-2-(3,5-dimethoxyphenyl)vinyl]phenol; UNII-26R60S6A5I; 3,5-Dimethoxy-4'-hydroxy-trans-stilbene; 3,5-Dimethoxy-4'-hydroxystilbene; 18259-15-9; trans-3,5-dimethoxy-4'-hydroxystilbene; CHEMBL83527; CHEBI:8630; VLEUZFDZJKSGMX-ONEGZZNKSA-N; 4-((E)-2-(3,5-dimethoxyphenyl)ethenyl)phenol; 26R60S6A5I; Pterostilbene, Pterocarpus; pterostilbene
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 256.3
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C16H16O3
IUPAC Name
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
Canonical SMILES
COC1=CC(=CC(=C1)/C=C/C2=CC=C(C=C2)O)OC
InChI
InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
InChIKey
VLEUZFDZJKSGMX-ONEGZZNKSA-N
Cross-matching ID
PubChem CID
5281727
ChEBI ID
CHEBI:8630
CAS Number
537-42-8
TTD ID
D00AII

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fusion protein Bcr-Abl (Bcr-Abl) TTS7G69 BCR_HUMAN-ABL1_HUMAN Inhibitor [2]
Peroxisome proliferator-activated receptor alpha (PPARA) TTJ584C PPARA_HUMAN Agonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
10 kDa heat shock protein, mitochondrial (HSPE1) OT7JSZLB CH10_HUMAN Gene/Protein Processing [4]
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Post-Translational Modifications [5]
Alpha-methylacyl-CoA racemase (AMACR) OTUU22PK AMACR_HUMAN Gene/Protein Processing [6]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [6]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [6]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [7]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [8]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [8]
C-X-C motif chemokine 3 (CXCL3) OTSL94KH CXCL3_HUMAN Gene/Protein Processing [9]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) 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
Peroxisome proliferator-activated receptor alpha (PPARA) DTT PPARA 1.74E-01 -0.17 -0.3
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2681).
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 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 593).
4 Proteomic identification of pterostilbene-mediated anticancer activities in HepG2 cells. Chem Res Toxicol. 2014 Jul 21;27(7):1243-52. doi: 10.1021/tx5001392. Epub 2014 Jul 1.
5 ERK5/HDAC5-mediated, resveratrol-, and pterostilbene-induced expression of MnSOD in human endothelial cells. Mol Nutr Food Res. 2016 Feb;60(2):266-77. doi: 10.1002/mnfr.201500466. Epub 2015 Oct 23.
6 In vitro evaluation of the cytotoxic, anti-proliferative and anti-oxidant properties of pterostilbene isolated from Pterocarpus marsupium. Toxicol In Vitro. 2010 Jun;24(4):1215-28. doi: 10.1016/j.tiv.2010.02.007. Epub 2010 Feb 10.
7 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.
8 Pterostilbene exerts antitumor activity against human osteosarcoma cells by inhibiting the JAK2/STAT3 signaling pathway. Toxicology. 2013 Feb 8;304:120-31. doi: 10.1016/j.tox.2012.12.018. Epub 2013 Jan 8.
9 Genomic analysis of pterostilbene predicts its antiproliferative effects against pancreatic cancer in vitro and in vivo. J Gastrointest Surg. 2012 Jun;16(6):1136-43. doi: 10.1007/s11605-012-1869-7. Epub 2012 Mar 27.
10 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.