ChemFOnt: Showing chemical card for Masoprocol (CFc000008722)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:37 UTC

Chemfont ID

CFc000008722

Molecule Identification

Common Name

Masoprocol

Definition

Masoprocol, also known as actinex or meso-ndga, belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, or feeling faint, wheezing or trouble in breathing. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known. Masoprocol is a drug which is used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated). It also serves as an antioxidant in fats and oils. Masoprocol is a potentially toxic compound. It is not known exactly how masoprocol works. Although the exact mechanism of action is not known, studies have shown that masoprocol is a potent 5-lipoxygenase inhibitor and has antiproliferative activity against keratinocytes in tissue culture, but the relationship between this activity and its effectiveness in actinic keratoses is unknown. A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Actinex	ChEBI
CHX 100	ChEBI
CHX-100	ChEBI
Erythro-nordihydroguaiaretic acid	ChEBI
Masoprocolum	ChEBI
Meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane	ChEBI
Meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane	ChEBI
Meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)	ChEBI
Meso-4,4'-(2,3-dimethyltetramethylene)dipyrocatechol	ChEBI
Meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol	ChEBI
Meso-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butan	ChEBI
Meso-ndga	ChEBI
Meso-nordihydroguaiaretic acid	ChEBI
Erythro-nordihydroguaiaretate	Generator
Meso-b,g-dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butan	Generator
Meso-β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butan	Generator
Meso-nordihydroguaiaretate	Generator
Meso-b,g-dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butan	HMDB
Dihydronorguaiaretic acid	HMDB
NDGA	HMDB
Nordihydroguaiaretic acid	HMDB
Nordihydroguairaretic acid	HMDB
Meso nordihydroguaiaretic acid	HMDB
Acid, meso-nordihydroguaiaretic	HMDB
(R,s)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol	HMDB
Nordihydroguaiaretic acid, (r,s)-isomer	HMDB
Nordihydroguaiaretate	HMDB

Chemical Formula

C₁₈H₂₂O₄

Average Molecular Weight

302.3649

Monoisotopic Molecular Weight

302.151809192

IUPAC Name

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

Traditional Name

masoprocol

CAS Registry Number

27686-84-6

SMILES

C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1

InChI Identifier

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+

InChI Key

HCZKYJDFEPMADG-TXEJJXNPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
Phenylpropane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nordihydroguaiaretic acid (CHEBI:73468 )
Lignans (C10719 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014325)
Membrane (HMDB: HMDB0014325)

Source

Exogenous

Exogenous (HMDB: HMDB0014325)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.44	ALOGPS
logP	4.76	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.62 m³·mol⁻¹	ChemAxon
Polarizability	33.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon