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

• ChemBase编号: 64
• 分子式: C18H22O4
• 平均质量: 302.36488
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
• IUPAC传统名: masoprocol
• 商标名: Actinex
• 别名: Dihydronorguaiaretic acid; Masoprocolum [INN-Latin]; Nordihydroguaiaretic acid; Nordihydroguairaretic acid; NDGA; meso-Nordihydroguaiaretic acid; meso-NDGA; Masoprocol

登记号

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

理论计算性质

JChem

• Acid pKa: 9.206547
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): 4.758438
• LogD (pH = 7.4): 4.7518115
• Log P: 4.7585225
• 摩尔折射率: 86.619 cm^3
• 极化性: 33.23442 Å^3
• 极化表面积: 80.92 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -4.35
• 溶解度: 1.36e-02 g/l

分子性质

理化性质

• 疏水性(logP): 5.8

详细说明

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 Masoprocol was withdrawn from the U.S. market in June 1996.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