2-Acetyl-3-methyl-1,6,8-trihydroxynaphthalene

Details

• Internal ID: 2a59803b-9b73-4033-bd73-6ffc229aa236
• Taxonomy: Benzenoids > Naphthalenes > Naphthols and derivatives
• IUPAC Name: 1-(1,6,8-trihydroxy-3-methylnaphthalen-2-yl)ethanone
• SMILES (Canonical): CC1=CC2=CC(=CC(=C2C(=C1C(=O)C)O)O)O
• SMILES (Isomeric): CC1=CC2=CC(=CC(=C2C(=C1C(=O)C)O)O)O
• InChI: InChI=1S/C13H12O4/c1-6-3-8-4-9(15)5-10(16)12(8)13(17)11(6)7(2)14/h3-5,15-17H,1-2H3
• InChI Key: MUWYBCVOKHQYED-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.23 g/mol
• Exact Mass: 232.07355886 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 2-acetyl-3-methyl-1,6,8-trihydroxynaphthalene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9903	99.03%
Caco-2	+	0.6770	67.70%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7959	79.59%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9215	92.15%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8837	88.37%
P-glycoprotein inhibitior	-	0.9385	93.85%
P-glycoprotein substrate	-	0.9203	92.03%
CYP3A4 substrate	-	0.5666	56.66%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	+	0.6603	66.03%
CYP2C9 inhibition	+	0.7893	78.93%
CYP2C19 inhibition	+	0.6643	66.43%
CYP2D6 inhibition	-	0.7845	78.45%
CYP1A2 inhibition	+	0.9664	96.64%
CYP2C8 inhibition	-	0.6156	61.56%
CYP inhibitory promiscuity	+	0.6792	67.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8422	84.22%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9834	98.34%
Eye irritation	+	0.9543	95.43%
Skin irritation	+	0.6026	60.26%
Skin corrosion	-	0.8889	88.89%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6972	69.72%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6179	61.79%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6172	61.72%
Acute Oral Toxicity (c)	III	0.8472	84.72%
Estrogen receptor binding	+	0.6829	68.29%
Androgen receptor binding	-	0.5097	50.97%
Thyroid receptor binding	-	0.7124	71.24%
Glucocorticoid receptor binding	+	0.6535	65.35%
Aromatase binding	-	0.6170	61.70%
PPAR gamma	-	0.5657	56.57%
Honey bee toxicity	-	0.9487	94.87%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9836	98.36%

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	95.74%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	89.45%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.48%	93.65%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.25%	96.12%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.73%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.78%	93.10%
CHEMBL4208	P20618	Proteasome component C5	84.31%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.85%	94.00%
CHEMBL2581	P07339	Cathepsin D	82.25%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.92%	94.42%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.85%	92.68%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.24%	95.56%

Plants that contains it

• Senna tora

Cross-Links

• PubChem: 23643241
• LOTUS: LTS0158914
• wikiData: Q105172794