3,8-Dihydroxy-2,5-dimethoxy-6-methylnaphthalene-1,4-dione

Details

• Internal ID: 7af4e464-2fac-4f48-9940-e4c5f0f53fa9
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 3,8-dihydroxy-2,5-dimethoxy-6-methylnaphthalene-1,4-dione
• InChI: InChI=1S/C13H12O6/c1-5-4-6(14)7-8(12(5)18-2)9(15)11(17)13(19-3)10(7)16/h4,14,17H,1-3H3
• InChI Key: GHDGVDSFWGUXAE-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₆
• Molecular Weight: 264.23 g/mol
• Exact Mass: 264.06338810 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.50
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	-	0.5831	58.31%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9519	95.19%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9250	92.50%
P-glycoprotein inhibitior	-	0.9054	90.54%
P-glycoprotein substrate	-	0.9708	97.08%
CYP3A4 substrate	-	0.5621	56.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8476	84.76%
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	-	0.8284	82.84%
CYP inhibitory promiscuity	+	0.6251	62.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9056	90.56%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9791	97.91%
Eye irritation	+	0.9754	97.54%
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	-	0.7666	76.66%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7527	75.27%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5389	53.89%
Acute Oral Toxicity (c)	II	0.5657	56.57%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	-	0.6939	69.39%
Thyroid receptor binding	-	0.6769	67.69%
Glucocorticoid receptor binding	+	0.6664	66.64%
Aromatase binding	-	0.6254	62.54%
PPAR gamma	+	0.5435	54.35%
Honey bee toxicity	-	0.8973	89.73%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	95.72%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.48%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.88%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.87%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.93%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.86%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.53%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.79%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.09%	93.40%
CHEMBL2535	P11166	Glucose transporter	82.69%	98.75%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.13%	97.21%

Plants that contains it

• Nepenthes rafflesiana

Cross-Links

• PubChem: 136680236
• LOTUS: LTS0265945
• wikiData: Q105008460