2-Methoxy-1,4-naphthoquinone

Details

• Internal ID: 14573f4f-669d-479d-9662-9089287ca9da
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 2-methoxynaphthalene-1,4-dione
• SMILES (Canonical): COC1=CC(=O)C2=CC=CC=C2C1=O
• SMILES (Isomeric): COC1=CC(=O)C2=CC=CC=C2C1=O
• InChI: InChI=1S/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3
• InChI Key: OBGBGHKYJAOXRR-UHFFFAOYSA-N
• Popularity: 102 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.18 g/mol
• Exact Mass: 188.047344113 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.60
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 2348-82-5
• 2-methoxynaphthalene-1,4-dione
• 2-Methoxynaphthoquinone
• 2-Methoxy-p-naphthoquinone
• lawsone methyl ether
• 1,4-Naphthalenedione, 2-methoxy-
• 1,4-NAPHTHOQUINONE, 2-METHOXY-
• 2-Methoxy-1,4-naphthalenedione
• 2-methoxy-1,4-dihydronaphthalene-1,4-dione
• NSC 31530
• 2-methoxy-1,4-napthoquinone
• UNII-39020BUT1D
• AI3-17893
• CHEMBL106562
• 2-Methoxy-[1,4]naphthoquinone
• CHEBI:69522
• 39020BUT1D
• NSC-31530
• O-METHYLLAWSONE
• D04OXY
• 2-ethoxy-1,4-aphthoquinone
• MLS002472995
• SCHEMBL571061
• DTXSID1062338
• BDBM24775
• OBGBGHKYJAOXRR-UHFFFAOYSA-
• 2-methoxy-naphthalene-1,4-dione
• HMS1607J05
• 2-methoxy-1,4-naphthoquinone, 2
• CAA34882
• HY-N7116
• NSC31530
• s3661
• 2-Methoxy-1,4-naphthoquinone, 98%
• AKOS001588285
• CCG-214807
• NCGC00247463-01
• AS-61144
• LS-95652
• SMR000112464
• CS-0030693
• FT-0634207
• EN300-332507
• A816744
• J-015127
• Q27137861
• InChI=1/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6008	60.08%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8173	81.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9657	96.57%
OATP1B3 inhibitior	+	0.9914	99.14%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7477	74.77%
P-glycoprotein inhibitior	-	0.9172	91.72%
P-glycoprotein substrate	-	0.9644	96.44%
CYP3A4 substrate	-	0.6424	64.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8070	80.70%
CYP3A4 inhibition	-	0.7338	73.38%
CYP2C9 inhibition	+	0.7121	71.21%
CYP2C19 inhibition	+	0.6312	63.12%
CYP2D6 inhibition	-	0.8610	86.10%
CYP1A2 inhibition	+	0.9735	97.35%
CYP2C8 inhibition	-	0.9304	93.04%
CYP inhibitory promiscuity	+	0.8107	81.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8556	85.56%
Carcinogenicity (trinary)	Non-required	0.4748	47.48%
Eye corrosion	-	0.9253	92.53%
Eye irritation	+	0.9863	98.63%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7801	78.01%
Micronuclear	+	0.5949	59.49%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.5508	55.08%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.8006	80.06%
Acute Oral Toxicity (c)	IV	0.3570	35.70%
Estrogen receptor binding	+	0.7020	70.20%
Androgen receptor binding	+	0.6912	69.12%
Thyroid receptor binding	-	0.6657	66.57%
Glucocorticoid receptor binding	-	0.8330	83.30%
Aromatase binding	-	0.5290	52.90%
PPAR gamma	-	0.7925	79.25%
Honey bee toxicity	-	0.7821	78.21%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9708	97.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	720 nM; 720 nM	IC50; IC50	PMID: 18318466; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.83%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.89%	82.69%
CHEMBL1951	P21397	Monoamine oxidase A	89.39%	91.49%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	89.13%	85.94%
CHEMBL2535	P11166	Glucose transporter	88.94%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	88.32%	96.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.73%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.78%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	84.27%	93.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.01%	96.09%

Plants that contains it

• Impatiens balsamina
• Impatiens glandulifera
• Rubia yunnanensis
• Swertia calycina

Cross-Links

• PubChem: 16871
• NPASS: NPC112552
• ChEMBL: CHEMBL106562
• LOTUS: LTS0215857
• wikiData: Q27137861