Masoprocol

Details

• Internal ID: 24af40b4-15cf-4702-bc86-11076b68696e
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): C[C@H](CC1=CC(=C(C=C1)O)O)[C@@H](C)CC2=CC(=C(C=C2)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+
• InChI Key: HCZKYJDFEPMADG-TXEJJXNPSA-N
• Popularity: 1,751 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.40 g/mol
• Exact Mass: 302.15180918 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• meso-NDGA
• 27686-84-6
• meso-Nordihydroguaiaretic acid
• Actinex
• Masoprocolum
• Masoprocolum [INN-Latin]
• CHX 100
• CHX-100
• INSM18
• meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
• 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-
• 4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
• UNII-7BO8G1BYQU
• 7BO8G1BYQU
• EINECS 248-606-6
• INSM-18
• Nordihydroguaiaretic acid from Larrea divaricata (creosote bush)
• erythro-nordihydroguaiaretic acid
• DTXSID5045178
• CHEBI:73468
• ORISTAR NHGA
• NSC-4291
• Nordihydroguaiaretic acid (meso-form)
• NSC-682984
• 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
• CHEMBL313972
• DTXCID3025178
• meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane
• 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
• Masoprocolum (INN-Latin)
• MASOPROCOL (MART.)
• MASOPROCOL [MART.]
• nordihydroguaiaretate
• Masoprocol [USAN:INN]
• 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-
• 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
• nordihydroguiaretic acid
• C18H22O4
• meso Nordihydroguaiaretic Acid
• Acid, meso-Nordihydroguaiaretic
• meso-4-(4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol
• (R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol
• NCGC00015741-06
• Actinex (TN)
• NDHGA
• Nordihydroguaiaretsaure
• MASOPROCOL [INN]
• Masoprocol (USAN/INN)
• Nordihydroguaiaretic Acid, (R*,S*)-Isomer
• Lopac-N-5023
• MASOPROCOL [USAN]
• MASOPROCOL [VANDF]
• SCHEMBL3818
• 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
• MASOPROCOL [WHO-DD]
• Lopac0_000877
• BIDD:ER0127
• MASOPROCOL [ORANGE BOOK]
• rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
• BDBM22372
• L01XX10
• HMS3262P15
• TNP00263
• Tox21_110210
• Tox21_500877
• NORDIHYDROGUAIARETIC ACID [MI]
• AKOS016014015
• CCG-204959
• DB00179
• LP00877
• NORDIHYDROGUAIARETIC ACID [INCI]
• NCGC00015741-01
• NCGC00015741-02
• NCGC00015741-03
• NCGC00015741-07
• NCGC00094201-01
• NCGC00094201-02
• NCGC00094201-03
• NCGC00094201-04
• NCGC00094201-05
• NCGC00094201-06
• NCGC00261562-01
• NORDIHYDROGUAIARETIC ACID [WHO-DD]
• CAS-27686-84-6
• HY-109500
• CS-0031186
• EU-0100877
• 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)dibenzene-1,2-diol
• 4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
• 1050512-02-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9578	95.78%
Caco-2	+	0.7519	75.19%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8535	85.35%
OATP2B1 inhibitior	-	0.7071	70.71%
OATP1B1 inhibitior	+	0.9493	94.93%
OATP1B3 inhibitior	+	0.9316	93.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6765	67.65%
P-glycoprotein inhibitior	-	0.7833	78.33%
P-glycoprotein substrate	-	0.9637	96.37%
CYP3A4 substrate	-	0.7868	78.68%
CYP2C9 substrate	-	0.5629	56.29%
CYP2D6 substrate	+	0.3661	36.61%
CYP3A4 inhibition	-	0.5833	58.33%
CYP2C9 inhibition	+	0.8891	88.91%
CYP2C19 inhibition	+	0.8628	86.28%
CYP2D6 inhibition	+	0.8262	82.62%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9506	95.06%
CYP inhibitory promiscuity	+	0.5322	53.22%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6737	67.37%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9663	96.63%
Eye irritation	+	0.8463	84.63%
Skin irritation	-	0.6844	68.44%
Skin corrosion	-	0.6927	69.27%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9060	90.60%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	-	0.5803	58.03%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7894	78.94%
Acute Oral Toxicity (c)	III	0.8109	81.09%
Estrogen receptor binding	+	0.7988	79.88%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6475	64.75%
Glucocorticoid receptor binding	+	0.8063	80.63%
Aromatase binding	+	0.8289	82.89%
PPAR gamma	+	0.7519	75.19%
Honey bee toxicity	-	0.9480	94.80%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	158.5 nM	Potency	via Super-PRED
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	110 nM	IC50	via Super-PRED
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	100 nM; 110 nM; 631 nM	Potency; IC50; Potency	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	11 nM	IC50	via Super-PRED
CHEMBL2392	P06746	DNA polymerase beta	794.3 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	125.9 nM	Potency	via Super-PRED
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	380 nM	IC50	via Super-PRED
CHEMBL2111421	P05412	Transcription factor AP1	7.9 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	95.84%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL3492	P49721	Proteasome Macropain subunit	92.81%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.76%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.51%	99.15%
CHEMBL4208	P20618	Proteasome component C5	87.85%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.28%	94.73%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	81.13%	97.23%

Plants that contains it

• Larrea divaricata
• Larrea tridentata
• Schisandra chinensis

Cross-Links

• PubChem: 71398
• LOTUS: LTS0161715
• wikiData: Q6783851