Details of the Drug

General Information of Drug (ID: DMMVNZ0)

Drug Name
Masoprocol
Synonyms
NDGA; N 5023; TNP00263; Actinex (TN); Nordihydroguaiaretic acid (meso-form); (R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol; 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Indication
Disease Entry ICD 11 Status REF
Prostate cancer 2C82.0 Approved [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 302.4
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C18H22O4
IUPAC Name
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Canonical SMILES
C[C@H](CC1=CC(=C(C=C1)O)O)[C@@H](C)CC2=CC(=C(C=C2)O)O
InChI
InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+
InChIKey
HCZKYJDFEPMADG-TXEJJXNPSA-N
Cross-matching ID
PubChem CID
71398
ChEBI ID
CHEBI:73468
CAS Number
27686-84-6
DrugBank ID
DB00179
TTD ID
D0U3YB
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
Erbb2 tyrosine kinase receptor (HER2) TT6EO5L ERBB2_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
11-beta-hydroxysteroid dehydrogenase type 2 (HSD11B2) OTHF4H9U DHI2_HUMAN Gene/Protein Processing [3]
ALK tyrosine kinase receptor (ALK) OTV3P4V8 ALK_HUMAN Gene/Protein Processing [4]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [5]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [6]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [7]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [8]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [5]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 2A (CDKN2A) OTN0ZWAE CDN2A_HUMAN Gene/Protein Processing [9]
fMet-Leu-Phe receptor (FPR1) OTFF9I6W FPR1_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 Prostate cancer
ICD Disease Classification 2C82.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Erbb2 tyrosine kinase receptor (HER2) DTT ERBB2 5.67E-03 -1.26 -2.05
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: 4265).
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
3 Effect of the interaction between lipoxygenase pathway and progesterone on the regulation of hydroxysteroid 11-Beta dehydrogenase 2 in cultured human term placental trophoblasts. Biol Reprod. 2008 Mar;78(3):514-20.
4 Reactive oxygen species and lipoxygenases regulate the oncogenicity of NPM-ALK-positive anaplastic large cell lymphomas. Oncogene. 2009 Jul 23;28(29):2690-6.
5 Inhibition of AP-1 transcription activator induces myc-dependent apoptosis in HL60 cells. J Cell Biochem. 2004 Apr 1;91(5):973-86. doi: 10.1002/jcb.10768.
6 Nordihydroguaiaretic acid restores expression of silenced E-cadherin gene in human breast cancer cell lines and xenografts. Anticancer Drugs. 2008 Jun;19(5):487-94. doi: 10.1097/CAD.0b013e3282fd5310.
7 Inhibitors of arachidonic acid metabolism potentiate tumour necrosis factor-alpha-induced apoptosis in HL-60 cells. Eur J Pharmacol. 2001 Jul 13;424(1):1-11. doi: 10.1016/s0014-2999(01)01124-4.
8 Lipoxygenase inhibitors induce death receptor 5/TRAIL-R2 expression and sensitize malignant tumor cells to TRAIL-induced apoptosis. Cancer Sci. 2007 Sep;98(9):1417-23. doi: 10.1111/j.1349-7006.2007.00559.x. Epub 2007 Jul 23.
9 Reactivation of methylation-silenced tumor suppressor gene p16INK4a by nordihydroguaiaretic acid and its implication in G1 cell cycle arrest. Life Sci. 2008 Jan 30;82(5-6):247-55. doi: 10.1016/j.lfs.2007.11.013. Epub 2007 Dec 4.
10 [Effect of nordy on FPR function of malignant human glioma cell line U87]. Yao Xue Xue Bao. 2007 Mar;42(3):257-62.