General
Preferred name
NORDIHYDROGUAIARETIC ACID
Synonyms
NORDIHYDROGUARETIC ACID ()
Meso-Nordihydroguaiaretic Acid ()
Masoprocol ()
masoprocol ()
NDGA ()
Dihydronorguaiaretic Acid ()
PMID26560530-Compound-24 ()
Nordihydroguaiaretic acid (NDGA) ()
nordihydroguiaretic acid ()
CHX-100 ()
Actinex ()
meso-NDGA ()
Nordihydroguaiaretic acid ()
P&D ID
PD001362
CAS
500-38-9
27686-84-6
1413-68-9
103185-28-0
Tags
nuisance
natural product
drug
available
Drug Status
approved
withdrawn
Drug indication
Antineoplastic
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Although we show the non-isomeric molecule, the approved drug masoprocol is a specific stereoisomer of NGDA, with IUPAC name 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol (as shown in the PubChem record). The ChEMBL record displays the non-stereoisomeric molecule. PubChem lists 6 stereoisomers of this compound.
(GtoPdb)
DESCRIPTION
NDGA (Nordihydroguaiaretic acid), also known as masoprocol, is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. NDGA directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, NDGA inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrines; it may prevent leukocyte infiltration into tissues and the release of reactive oxygen species and, at higher concentrations, may also inhibit cyclooxygenase.
(BOC Sciences Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
9
Organisms
4
Compound Sets
19
BOC Sciences Bioactive Compounds
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugMAP
DrugMatrix
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
LSP-OptimalKinase library (Laboratory of Systems Pharmacology)
Mcule NIBR MoA Box Subset
MedChem Express Bioactive Compound Library
Novartis Chemogenetic Library (NIBR MoA Box)
Nuisance compounds in cellular assays
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
30
Molecular Weight
302.15
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
4
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
2
cLogP
3.57
TPSA
80.92
Fraction CSP3
0.33
Chiral centers
2.0
Largest ring
6.0
QED
0.64
Structural alerts
1
Nonspecific reactivity
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Pathway
oxidation-reduction
Apoptosis
Autophagy
Metabolic Enzyme/Protease
Target
antioxidant
Ferroptosis
Lipoxygenase
Apoptosis related,Autophagy,Epigenetic Reader Domain,Ferroptosis,HER2,IGF-1R,Lipoxygenase
MOA
Antioxidant
Antioxidant agent
Member status
virtual
Solubility
water, 4.969 mg/L @ 25 °C (est)
Source data
