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

Details

• Internal ID: 905d588e-2a2d-42e7-95d1-6cf9e3da8fc2
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)Cl
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)Cl
• InChI: InChI=1S/C11H7ClO3/c1-5-9(12)11(15)8-6(10(5)14)3-2-4-7(8)13/h2-4,13H,1H3
• InChI Key: LHPOSZYLQOYNDN-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₇ClO₃
• Molecular Weight: 222.62 g/mol
• Exact Mass: 222.0083718 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 3-Chlorplumbagin
• 3-Chloroplumbagin
• 3-chloro-5-hydroxy-2-methylnaphthalene-1,4-dione
• NSC362426
• CHLOROPLUMBAGIN
• SCHEMBL5174518
• DTXSID60320630
• NSC-362426

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5607	56.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8357	83.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9338	93.38%
OATP1B3 inhibitior	+	0.9558	95.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8916	89.16%
P-glycoprotein inhibitior	-	0.9745	97.45%
P-glycoprotein substrate	-	0.9728	97.28%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8474	84.74%
CYP3A4 inhibition	-	0.7372	73.72%
CYP2C9 inhibition	+	0.9338	93.38%
CYP2C19 inhibition	+	0.7650	76.50%
CYP2D6 inhibition	-	0.6161	61.61%
CYP1A2 inhibition	+	0.9240	92.40%
CYP2C8 inhibition	-	0.8984	89.84%
CYP inhibitory promiscuity	+	0.7355	73.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6898	68.98%
Carcinogenicity (trinary)	Non-required	0.4613	46.13%
Eye corrosion	-	0.9693	96.93%
Eye irritation	+	0.9491	94.91%
Skin irritation	+	0.6777	67.77%
Skin corrosion	-	0.8674	86.74%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8291	82.91%
Micronuclear	+	0.6530	65.30%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	+	0.6662	66.62%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.8291	82.91%
Acute Oral Toxicity (c)	II	0.6189	61.89%
Estrogen receptor binding	+	0.6688	66.88%
Androgen receptor binding	-	0.5356	53.56%
Thyroid receptor binding	-	0.6697	66.97%
Glucocorticoid receptor binding	-	0.4748	47.48%
Aromatase binding	-	0.5397	53.97%
PPAR gamma	+	0.5763	57.63%
Honey bee toxicity	-	0.9429	94.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.30%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	94.11%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.51%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	89.59%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.44%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.93%	96.67%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.04%	90.24%
CHEMBL1937	Q92769	Histone deacetylase 2	84.23%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.31%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.71%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.75%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.16%	99.23%

Plants that contains it

• Dionaea muscipula
• Diospyros maritima
• Drosera intermedia
• Drosophyllum lusitanicum
• Plumbago zeylanica

Cross-Links

• PubChem: 338719
• NPASS: NPC270483
• LOTUS: LTS0197827
• wikiData: Q82077975