2,3-Dimethoxy-1,4-naphthoquinone

Details

• Internal ID: 7d3750c1-44cd-4ba5-b3b6-ec5c71c31643
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 2,3-dimethoxynaphthalene-1,4-dione
• SMILES (Canonical): COC1=C(C(=O)C2=CC=CC=C2C1=O)OC
• SMILES (Isomeric): COC1=C(C(=O)C2=CC=CC=C2C1=O)OC
• InChI: InChI=1S/C12H10O4/c1-15-11-9(13)7-5-3-4-6-8(7)10(14)12(11)16-2/h3-6H,1-2H3
• InChI Key: ZEGDFCCYTFPECB-UHFFFAOYSA-N
• Popularity: 183 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.20 g/mol
• Exact Mass: 218.05790880 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 2,3-Dimethoxy-1,4-naphthoquinone
• 6956-96-3
• 2,3-dimethoxynaphthalene-1,4-dione
• NSC 69355
• 1,4-Naphthalenedione, 2,3-dimethoxy-
• 1,4-Naphthalenedione,2,3-dimethoxy-
• CHEBI:64215
• MFW94A3JEK
• CHEMBL402468
• 2,3-dimethoxy-1,4-naphthalenedione
• NSC-69355
• 2,3-DIMETHOXY-1,4-DIHYDRONAPHTHALENE-1,4-DIONE
• 2,3-Dimethoxynaphthoquinone
• UNII-MFW94A3JEK
• Lopac-D-5439
• NCIOpen2_003296
• Lopac0_000399
• MLS002153320
• SCHEMBL571557
• 2,3-Dimethoxynaphthoquinone #
• DTXSID8040935
• HMS3261O19
• 2,3-Dimethoxy[1,4]naphthoquinone
• BCP31298
• NSC69355
• Tox21_500399
• BDBM50504346
• HB3876
• MFCD00184331
• s6563
• AKOS022506394
• 2,3-DIMETHOXY-P-NAPHTHOQUINONE
• CCG-204492
• LP00399
• SDCCGSBI-0050385.P002
• NCGC00015348-01
• NCGC00015348-02
• NCGC00015348-03
• NCGC00015348-04
• NCGC00015348-05
• NCGC00015348-08
• NCGC00093826-01
• NCGC00093826-02
• NCGC00261084-01
• BS-17479
• SMR001230733
• HY-121026
• CS-0079331
• EU-0100399
• D 5439
• D81157
• SR-01000075819
• 2,3-Dimethoxy-1,4-naphthoquinone, >=99%, solid
• SR-01000075819-1
• Q27133127
• DiMeNQ;NSC 69355; NSC-69355; NSC69355;2,3-Dimethoxy-1,4-naphthoquinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.5904	59.04%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9733	97.33%
OATP1B3 inhibitior	+	0.9874	98.74%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8605	86.05%
P-glycoprotein inhibitior	-	0.9090	90.90%
P-glycoprotein substrate	-	0.9786	97.86%
CYP3A4 substrate	-	0.7016	70.16%
CYP2C9 substrate	-	0.8221	82.21%
CYP2D6 substrate	-	0.7749	77.49%
CYP3A4 inhibition	+	0.6167	61.67%
CYP2C9 inhibition	-	0.5248	52.48%
CYP2C19 inhibition	+	0.6136	61.36%
CYP2D6 inhibition	-	0.8139	81.39%
CYP1A2 inhibition	+	0.9522	95.22%
CYP2C8 inhibition	-	0.9885	98.85%
CYP inhibitory promiscuity	+	0.8225	82.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8756	87.56%
Carcinogenicity (trinary)	Non-required	0.5618	56.18%
Eye corrosion	-	0.9627	96.27%
Eye irritation	+	0.9713	97.13%
Skin irritation	-	0.6550	65.50%
Skin corrosion	-	0.9769	97.69%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7536	75.36%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6080	60.80%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.7178	71.78%
Acute Oral Toxicity (c)	II	0.4004	40.04%
Estrogen receptor binding	+	0.6471	64.71%
Androgen receptor binding	+	0.5726	57.26%
Thyroid receptor binding	-	0.6670	66.70%
Glucocorticoid receptor binding	-	0.8856	88.56%
Aromatase binding	-	0.5649	56.49%
PPAR gamma	-	0.7679	76.79%
Honey bee toxicity	-	0.8425	84.25%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9820	98.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.42%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.67%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.54%	96.67%
CHEMBL2535	P11166	Glucose transporter	85.51%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	80.93%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.76%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.15%	91.11%

Plants that contains it

• Newbouldia laevis

Cross-Links

• PubChem: 3136
• LOTUS: LTS0033176
• wikiData: Q27133127