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
Affected Organisms
Humans and other mammals
ATC Code
L01XX10: Masoprocol
L01XX: Other antineoplastic agents
L01X: OTHER ANTINEOPLASTIC AGENTS
L01: ANTINEOPLASTIC AGENTS
L: ANTINEOPLASTIC AND IMMUNOMODULATING 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
CHEMBL73468
CAS Number
27686-84-6
UNII
7BO8G1BYQU
DrugBank ID
DB00179
TTD ID
D0U3YB
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE 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
Erbb2 tyrosine kinase receptor (HER2) TT6EO5L ERBB2_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 2A (CDKN2A) OTN0ZWAE CDN2A_HUMAN Gene/Protein Processing [4]
fMet-Leu-Phe receptor (FPR1) OTFF9I6W FPR1_HUMAN Gene/Protein Processing [5]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [6]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [6]
Myc proto-oncogene protein (MYC) OTPV5LUK MYC_HUMAN Gene/Protein Processing [7]
Polyunsaturated fatty acid lipoxygenase ALOX12 (ALOX12) OTFL5KR5 LOX12_HUMAN Gene/Protein Processing [8]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [4]
Sex hormone-binding globulin (SHBG) OTPWU5IW SHBG_HUMAN Protein Interaction/Cellular Processes [9]
Transcription factor Jun (JUN) OTCYBO6X JUN_HUMAN Gene/Protein Processing [7]
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 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.
4 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.
5 [Effect of nordy on FPR function of malignant human glioma cell line U87]. Yao Xue Xue Bao. 2007 Mar;42(3):257-62.
6 Reactive oxygen species and lipoxygenases regulate the oncogenicity of NPM-ALK-positive anaplastic large cell lymphomas. Oncogene. 2009 Jul 23;28(29):2690-6.
7 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.
8 Assessing 12(S)-lipoxygenase inhibitory activity using colorectal cancer cells overexpressing the enzyme. Food Chem Toxicol. 2007 Mar;45(3):508-14. doi: 10.1016/j.fct.2006.08.013. Epub 2006 Aug 30.
9 Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and -fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27.