6-Acetyl-5,8-dihydroxy-2-methoxy-7-methylnaphthalene-1,4-dione

Details

• Internal ID: 0f942c83-2220-4acb-9078-83038de7d59e
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 6-acetyl-5,8-dihydroxy-2-methoxy-7-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=C2C(=O)C=C(C(=O)C2=C1O)OC)O)C(=O)C
• SMILES (Isomeric): CC1=C(C(=C2C(=O)C=C(C(=O)C2=C1O)OC)O)C(=O)C
• InChI: InChI=1S/C14H12O6/c1-5-9(6(2)15)14(19)10-7(16)4-8(20-3)13(18)11(10)12(5)17/h4,17,19H,1-3H3
• InChI Key: PHRQNTXVBVJWJE-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₆
• Molecular Weight: 276.24 g/mol
• Exact Mass: 276.06338810 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL3094516

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.6007	60.07%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8868	88.68%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8437	84.37%
P-glycoprotein inhibitior	-	0.9142	91.42%
P-glycoprotein substrate	-	0.9400	94.00%
CYP3A4 substrate	-	0.5485	54.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.6391	63.91%
CYP2C9 inhibition	-	0.6551	65.51%
CYP2C19 inhibition	-	0.5878	58.78%
CYP2D6 inhibition	-	0.7750	77.50%
CYP1A2 inhibition	+	0.8860	88.60%
CYP2C8 inhibition	-	0.7445	74.45%
CYP inhibitory promiscuity	+	0.6251	62.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9056	90.56%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9791	97.91%
Eye irritation	+	0.5558	55.58%
Skin irritation	-	0.6010	60.10%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7087	70.87%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.7527	75.27%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.6885	68.85%
Acute Oral Toxicity (c)	II	0.5657	56.57%
Estrogen receptor binding	+	0.6319	63.19%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.7916	79.16%
Glucocorticoid receptor binding	-	0.6064	60.64%
Aromatase binding	-	0.6639	66.39%
PPAR gamma	-	0.5191	51.91%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9856	98.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.28%	94.45%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	86.97%	92.68%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.54%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.23%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.50%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.57%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.04%	97.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.59%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.51%	96.00%

Plants that contains it

• Stuhlmannia moavi

Cross-Links

• PubChem: 72737556
• NPASS: NPC193169
• ChEMBL: CHEMBL3094516