4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol

• ChemBase ID: 64
• Molecular Formular: C18H22O4
• Molecular Mass: 302.36488
• Monoisotopic Mass: 302.15180918
• SMILES: Oc1cc(C[C@@H]([C@@H](Cc2cc(O)c(O)cc2)C)C)ccc1O
• Canonical SMILES: C[C@H]([C@@H](Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
• IUPAC Traditional name: masoprocol
• Brand Name: Actinex
• Synonyms: Dihydronorguaiaretic acid; Masoprocolum [INN-Latin]; Nordihydroguaiaretic acid; Nordihydroguairaretic acid; NDGA; meso-Nordihydroguaiaretic acid; meso-NDGA; Masoprocol

Database IDs

• CAS Number: 500-38-9
• PubChem SID: 46508042; 160963527
• PubChem CID: 71398

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.206547
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 4.758438
• LogD (pH = 7.4): 4.7518115
• Log P: 4.7585225
• Molar Refractivity: 86.619 cm^3
• Polarizability: 33.23442 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -4.35
• Solubility (Water): 1.36e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.8

DETAILS

DrugBank - DB00179

• Drug Groups: approved
• Description: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils. [PubChem]
• Indication: Used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
• Pharmacology: Masoprocol is a novel antineoplastic agent. It is not known exactly how masoprocol works. Laboratory experiments have shown that masoprocol prevents cells similar to the ones found in actinic keratoses from multiplying. Masoprocol was withdrawn from the U.S. market in June 1996.
• Toxicity: Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
• Affected Organisms: Humans and other mammals
• Absorption: Less than 1%-2% is absorbed through the skin over a 4-day period following application.
• External Links: Wikipedia