3-Bromo-5-hydroxy-2-methylnaphthalene-1,4-dione

Details

• Internal ID: 4a3e6945-9bf6-4237-bd14-a3caf3f17790
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 3-bromo-5-hydroxy-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)Br
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)Br
• InChI: InChI=1S/C11H7BrO3/c1-5-9(12)11(15)8-6(10(5)14)3-2-4-7(8)13/h2-4,13H,1H3
• InChI Key: NIQBOMVXAMPKNW-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₇BrO₃
• Molecular Weight: 267.07 g/mol
• Exact Mass: 265.95786 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 3-bromo-5-hydroxy-2-methylnaphthalene-1,4-dione
• 1,4-Naphthalenedione, 3-bromo-5-hydroxy-2-methyl-
• NSC621605
• Plumbagin, 3-bromo:
• DTXSID20326911
• NSC-621605

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6961	69.61%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7380	73.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9439	94.39%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8974	89.74%
P-glycoprotein inhibitior	-	0.9734	97.34%
P-glycoprotein substrate	-	0.9532	95.32%
CYP3A4 substrate	-	0.5446	54.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8456	84.56%
CYP3A4 inhibition	-	0.7001	70.01%
CYP2C9 inhibition	+	0.9379	93.79%
CYP2C19 inhibition	+	0.6582	65.82%
CYP2D6 inhibition	-	0.7741	77.41%
CYP1A2 inhibition	+	0.9188	91.88%
CYP2C8 inhibition	-	0.9380	93.80%
CYP inhibitory promiscuity	+	0.7561	75.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7230	72.30%
Carcinogenicity (trinary)	Danger	0.4216	42.16%
Eye corrosion	-	0.9599	95.99%
Eye irritation	+	0.9673	96.73%
Skin irritation	+	0.5825	58.25%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8061	80.61%
Micronuclear	+	0.7030	70.30%
Hepatotoxicity	+	0.8178	81.78%
skin sensitisation	+	0.5829	58.29%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6826	68.26%
Acute Oral Toxicity (c)	III	0.4495	44.95%
Estrogen receptor binding	-	0.6700	67.00%
Androgen receptor binding	-	0.6596	65.96%
Thyroid receptor binding	-	0.7353	73.53%
Glucocorticoid receptor binding	+	0.5692	56.92%
Aromatase binding	-	0.8081	80.81%
PPAR gamma	-	0.6307	63.07%
Honey bee toxicity	-	0.9656	96.56%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.82%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.47%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	91.48%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	91.25%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	90.67%	94.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.89%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.49%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.24%	96.67%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.76%	93.65%
CHEMBL2535	P11166	Glucose transporter	83.18%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.00%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%

Plants that contains it

• Diospyros maritima

Cross-Links

• PubChem: 359908
• LOTUS: LTS0222758
• wikiData: Q82088154