Compound: Masoprocol
SMILES: Oc1c(O)ccc(c1)C[C@@H]([C@@H](Cc2cc(O)c(O)cc2)C)C
InChIKey: HCZKYJDFEPMADG-TXEJJXNPSA-N
Synonyms: Masoprocol, 27686-84-6, meso-NDGA, meso-Nordihydroguaiaretic acid, Actinex, Masoprocolum, CHX 100, CHX-100, meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol, Dihydronorguaiaretic acid, 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-, ORISTAR NHGA, 7BO8G1BYQU, INSM-18, 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol, erythro-nordihydroguaiaretic acid, DTXSID5045178, NSC-4291, (R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol, NSC-682984, DTXCID3025178, CHEBI:73468, meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane, Dinorguaiaretic acid, dihydro-, meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol), meso-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butan, 1,2-Benzenediol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis-, rel-, meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol, 1,2-Benzenediol, 4,4'-[(2R,3S)-2,3-dimethyl-1,4-butanediyl]bis-, rel-, 4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol, 4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol, 4-((2R,3S)-4-(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTYL)BENZENE-1,2-DIOL, meso Nordihydroguaiaretic Acid, Acid, meso-Nordihydroguaiaretic, 4-((2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol, meso-4-(4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol, 4-((2S,3R)-3-((3,4-dihydroxyphenyl)methyl)-2-methylbutyl)benzene-1,2-diol, NDHGA, RefChem:57406, 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(1,2-benzenediol), L01XX10, Nordihydroguaiaretic Acid, (R*,S*)-, 248-606-6, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, NSC4291, Masoprocolum [INN-Latin], INSM18, 4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol), Nordihydroguaiaretic acid from Larrea divaricata (creosote bush), nordihydroguiaretic acid, C18H22O4, CHEMBL313972, nordihydroguaiaretate, Masoprocol [USAN:INN], EINECS 248-606-6, UNII-7BO8G1BYQU, NCGC00015741-06, Actinex (TN), Nordihydroguaiaretic acid (meso-form), Nordihydroguaiaretsaure, MASOPROCOL [INN], Masoprocol (USAN/INN), Lopac-N-5023, MASOPROCOL [USAN], MASOPROCOL [VANDF], MASOPROCOL [MART.], SCHEMBL3818, MASOPROCOL [WHO-DD], Lopac0_000877, BIDD:ER0127, orb1689335, MASOPROCOL [ORANGE BOOK], SCHEMBL29350884, SCHEMBL29355090, BDBM22372, HCZKYJDFEPMADG-TXEJJXNPSA-N, HMS3262P15, TNP00263, Tox21_110210, Tox21_500877, EBC-26544, EX-A10675, NORDIHYDROGUAIARETIC ACID [MI], AKOS016014015, CCG-204959, DB00179, LP00877, NCGC00015741-01, NCGC00015741-02, NCGC00015741-03, NCGC00015741-07, NCGC00094201-01, NCGC00094201-02, NCGC00094201-03, NCGC00094201-04, NCGC00094201-05, NCGC00094201-06, NCGC00261562-01, DA-55243, NORDIHYDROGUAIARETIC ACID [WHO-DD], CAS-27686-84-6, HY-109500, CS-0031186, EU-0100877, NS00068157, D04862, N 5023, EN300-18167073, SR-01000076028, NCGC00015741-06!NORDIHYDROGUAIARETIC ACID, Q6783851, SR-01000076028-1, 4,4'-[(2R,3S)-2,3-Dimethylbutane-1,4-diyl]di(benzene-1,2-diol), 4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol, rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol), 1050512-02-1
Theoretical properties:
molecular_formula: C18H22O4
molecular_weight: 302.4 g/mol
exact_mass: 302.15180918 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 22
topological_polar_surface_area: 80.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 1.36e-02 g/L
Descriptions:
pubchem: Masoprocol is the meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase. It has a role as a metabolite, a hypoglycemic agent, an antineoplastic agent and a lipoxygenase inhibitor.
chebi: The <i>meso</i>-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, <em>Larrea divaricata</em>, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.
chembl: MASOPROCOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Masoprocol is an antineoplastic drug used to treat skin growths caused by sun exposure. It is the meso form of nordihydroguaiaretic acid that is taken by mouth. The substance is being studied in the treatment of prostate cancer. 
Masoprocol is also called NDGA, and Actinex.