CAS 500-38-9|CAS 27686-84-6|Dihydronorguaiaretic acid|Actinex|Nordihydroguairaretic acid|meso-Nordihydroguaiaretic acid|4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol|maso...

General Information

Structure

Molecular Formula

C₁₈H₂₂O₄

Molecular Mass

302.36488

Exact Mass

302.15180918

Charge

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

Canonic Smiles

C[C@H]([C@@H](Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)O)O

Isomeric Smiles

Oc1cc(C[C@@H]([C@@H](Cc2cc(O)c(O)cc2)C)C)ccc1O

Calculated Properties

JChem

LogD (pH = 7.4)

4.75

LogD (pH = 5.5)

4.76

Log P

4.76

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.21

Polar Surface Area

80.92

Polarizability

33.49

Molar Refractivity

86.62

LOG S

-4.16

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

meso-NDGANordihydroguaiaretic acidMasoprocolum [INN-Latin]NDGANordihydroguairaretic acidMasoprocolDihydronorguaiaretic acidmeso-Nordihydroguaiaretic acidmeso-NDGAerythro-nordihydroguaiaretic acidmeso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutaneCHX-100CHX 100meso-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butanmeso-2,3-bis(3,4-dihydroxyphenylmethyl)butanemeso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)meso-4,4'-(2,3-dimethyltetramethylene)dipyrocatecholmasoprocolmeso-nordihydroguaiaretic acidmeso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol

IUPAC name

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

IUPAC Traditional name

masoprocol

Brand Name

Actinex

International Nonproprietary Name (INN)

masoprocolummasoprocol

Names and Identifiers

Registration numbers

PubChem SID

16096352746508042163426050

PubChem CID

71398

CAS Number

500-38-927686-84-6

PubMed Citation Links

1041137384129809169274100275871581425310950827102064301869646961775580404251867293011016888

Reaxys Registry

20568269874298

CHEBI ID

CHEBI:73468

MetaboLights Database

CompTox Database

KEGG ID

BRENDA Database

BKMS React Database

BindingDB Database

CHEMBL

SureChEMBL Database

Drug Central Database

KEGG DRUG Database

DrugBank ID

HMDB Database

KNApSAcK Database

BRENDA Ligand Database

143361

Wikipedia Title

Masoprocol

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

5.8

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

ChEBI

CHEBI:73468

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.

Molecule Details

References

PubChem Literature

No Data Available

Click here to submit data

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties