General
Preferred name
NORDIHYDROGUAIARETIC ACID
Synonyms
NORDIHYDROGUARETIC ACID ()
Meso-Nordihydroguaiaretic Acid ()
Masoprocol ()
masoprocol ()
NDGA ()
Dihydronorguaiaretic Acid ()
PMID26560530-Compound-24 ()
Nordihydroguaiaretic acid (NDGA) ()
nordihydroguiaretic acid ()
Nordihydroguaiaretic acid ()
P&D ID
PD001362
CAS
27686-84-6
500-38-9
1413-68-9
103185-28-0
Tags
available
drug
natural product
nuisance
Drug Status
approved
withdrawn
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
Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8 ¦ÌM) and tyrosine kinase inhibitor.
PRICE
29
DESCRIPTION
Nordihydroguaiaretic acid (NDGA) is a natural product, extracted from Pole Fork Kelaroa, and is a lipoxygenase (5-LOX) inhibitor (IC50=8 ??M). Nordihydroguaiaretic acid possesses antioxidant and free radical scavenging properties.
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
Nordihydroguaiaretic acid inhibits leukotriene B4 (LTB4) formation in human polymorphonuclear leukocytes mediated by 5-lipoxygenase with IC50 = 85 nM; for 5-lipoxygenase from rat basophilic leukemia (RBL-1) cells IC50 = 10 nM. It also inhibits cholinesterase (IC50= 0.78nM) and carbonic anhydrase 2 (Ki = 2.56 nM), carbonic anhydrase 1 (Ki = 2.81 nM)
(Enamine Bioactive Compounds)
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)
DESCRIPTION
Nordihydroguaiaretic acid (NDGA) is a natural product, extracted from Pole Fork Kelaroa, and is a lipoxygenase (5-LOX) inhibitor (IC50=8 μM). Nordihydroguaiaretic acid possesses antioxidant and free radical scavenging properties.
(TargetMol Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
9
Organisms
4
Compound Sets
22
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
CZ-OPENSCREEN Bioactive Library
DrugMAP
DrugMatrix
Enamine Bioactive Compounds
EU-OPENSCREEN Bioactive Compound Library
EUbOPEN Chemogenomics 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
Related compounds
Custom attributes
(extracted from source data)
MOA
Antioxidant
Antioxidant agent
Member status
virtual
Pathway
Apoptosis
Autophagy
Metabolism
oxidation-reduction
Metabolic Enzyme/Protease
Target
Ferroptosis
Lipoxygenase
Apoptosis related,Autophagy,Epigenetic Reader Domain,Ferroptosis,HER2,IGF-1R,Lipoxygenase
antioxidant
Solubility
water, 4.969 mg/L @ 25 °C (est)
Recommended Cell Concentration
None
Source data
