Details of the Drug

General Information of Drug (ID: DM3RWXL)

Drug Name
Resveratrol
Synonyms
Resveratrol; Resvida; KUC104385N; R 5010; SRT 501; Cis-resveratrol; PREVENTION 8 (RESVERATROL); RM-1812; SRT-501; Trans-resveratrol; CU-01000001503-3; KSC-10-164; Resveratrol-3-sulfate; Trans-3,4',5-trihydroxystilbene; Trans-3,4′,5-Trihydroxystilbene; Trans-1,2-(3,4',5-Trihydroxydiphenyl)ethylene; (E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol
Indication
Disease Entry ICD 11 Status REF
Giant cell arteritis 4A44.2 Phase 3 [1]
Rheumatoid arthritis FA20 Phase 3 [1]
Systemic sclerosis 4A42 Phase 3 [1]
Colorectal cancer 2B91.Z Discontinued in Phase 2 [2]
Middle East Respiratory Syndrome (MERS) 1D64 Preclinical [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 228.24
Logarithm of the Partition Coefficient (xlogp) 3.1
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C14H12O3
IUPAC Name
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Canonical SMILES
C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)O
InChI
InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
InChIKey
LUKBXSAWLPMMSZ-OWOJBTEDSA-N
Cross-matching ID
PubChem CID
445154
ChEBI ID
CHEBI:45713
CAS Number
501-36-0
DrugBank ID
DB02709
TTD ID
D0U3EP
VARIDT ID
DR00287
INTEDE ID
DR1406
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
NAD-dependent deacetylase sirtuin-1 (SIRT1) TTUF2HO SIR1_HUMAN Inhibitor [4]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Modulator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [6]
Multidrug resistance-associated protein 1 (ABCC1) DTSYQGK MRP1_HUMAN Substrate [6]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [8]
NADPH-dependent curcumin reductase (curA) DEZWDKE CURA_ECOLI Substrate [9]
Sulfotransferase 1C2 (SULT1C2) DEYMAD4 ST1C2_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1 (PLCD1) OT6WFVXZ PLCD1_HUMAN Gene/Protein Processing [11]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 (PLCG1) OTSBQR6D PLCG1_HUMAN Gene/Protein Processing [12]
116 kDa U5 small nuclear ribonucleoprotein component (EFTUD2) OT3X7QG2 U5S1_HUMAN Post-Translational Modifications [13]
14-3-3 protein beta/alpha OTGBS3RF 1433B_HUMAN Gene/Protein Processing [14]
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [12]
14-3-3 protein theta OTWG7F3H 1433T_HUMAN Gene/Protein Processing [15]
14-3-3 protein zeta/delta OT2TKG9P 1433Z_HUMAN Gene/Protein Processing [12]
2'-5'-oligoadenylate synthase-like protein (OASL) OTZ05YRP OASL_HUMAN Gene/Protein Processing [16]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [17]
3-oxo-5-alpha-steroid 4-dehydrogenase 2 (SRD5A2) OTTG0NFD S5A2_HUMAN Gene/Protein Processing [18]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Giant cell arteritis
ICD Disease Classification 4A44.2
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
NAD-dependent deacetylase sirtuin-1 (SIRT1) DTT SIRT1 7.82E-01 -0.16 -0.27
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.77E-01 0.32 0.73
Multidrug resistance-associated protein 1 (ABCC1) DTP MRP1 3.82E-01 1.16E-01 9.50E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 1.85E-01 -1.34E-01 -4.20E-01
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 6.77E-01 3.03E-02 1.51E-01
Sulfotransferase 1C2 (SULT1C2) DME SULT1C2 8.34E-01 6.06E-03 3.55E-02
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 5.25E-01 -4.04E-01 -5.29E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800018787)
3 Effective inhibition of MERS-CoV infection by resveratrol. BMC Infect Dis. 2017 Feb 13;17(1):144.
4 Sirtuin modulators: an updated patent review (2012 - 2014).Expert Opin Ther Pat. 2015 Jan;25(1):5-15.
5 Resveratrol is a peroxidase-mediated inactivator of COX-1 but not COX-2: a mechanistic approach to the design of COX-1 selective agents. J Biol Chem. 2004 May 21;279(21):22727-37.
6 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
7 The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9.
8 Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol. 2004 Aug 15;68(4):773-82.
9 Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism. Proc Natl Acad Sci U S A. 2011 Apr 19;108(16):6615-20.
10 Correlation of reactive oxygen species levels with resveratrol sensitivities of anaplastic thyroid cancer cells. Oxid Med Cell Longev. 2018 Jul 10;2018:6235417.
11 Molecular mechanisms of resveratrol action in lung cancer cells using dual protein and microarray analyses. Cancer Res. 2007 Dec 15;67(24):12007-17. doi: 10.1158/0008-5472.CAN-07-2464.
12 Differential expression of genes induced by resveratrol in LNCaP cells: P53-mediated molecular targets. Int J Cancer. 2003 Mar 20;104(2):204-12.
13 Phosphoproteomics reveals resveratrol-dependent inhibition of Akt/mTORC1/S6K1 signaling. J Proteome Res. 2014 Dec 5;13(12):5734-42. doi: 10.1021/pr500714a. Epub 2014 Oct 29.
14 Pleiotropic combinatorial transcriptomes of human breast cancer cells exposed to mixtures of dietary phytoestrogens. Food Chem Toxicol. 2009 Apr;47(4):787-95.
15 A human tRNA synthetase is a potent PARP1-activating effector target for resveratrol. Nature. 2015 Mar 19;519(7543):370-3. doi: 10.1038/nature14028. Epub 2014 Dec 22.
16 A novel long noncoding RNA AK001796 acts as an oncogene and is involved in cell growth inhibition by resveratrol in lung cancer. Toxicol Appl Pharmacol. 2015 Jun 1;285(2):79-88.
17 Resveratrol potentiates effect of simvastatin on inhibition of mevalonate pathway in human endometrial stromal cells. J Clin Endocrinol Metab. 2013 Mar;98(3):E455-62.
18 Examining the genomic influence of skin antioxidants in vitro. Mediators Inflamm. 2010;2010.