8-Hydroxy-2-(5-hydroxy-7-methyl-1,4-dioxonaphthalen-2-yl)-6-methylnaphthalene-1,4-dione

Details

• Internal ID: a31de1ba-f86f-4f5d-b4bc-18cf57072d2c
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 8-hydroxy-2-(5-hydroxy-7-methyl-1,4-dioxonaphthalen-2-yl)-6-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C(=CC2=O)C3=CC(=O)C4=C(C3=O)C=C(C=C4O)C
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C(=CC2=O)C3=CC(=O)C4=C(C3=O)C=C(C=C4O)C
• InChI: InChI=1S/C22H14O6/c1-9-3-13-15(23)7-12(22(28)20(13)17(25)6-9)11-8-18(26)19-14(21(11)27)4-10(2)5-16(19)24/h3-8,24-25H,1-2H3
• InChI Key: LKTUQZVPNZGGCU-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₄O₆
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.07903816 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7113	71.13%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.9018	90.18%
OATP2B1 inhibitior	-	0.7023	70.23%
OATP1B1 inhibitior	+	0.9144	91.44%
OATP1B3 inhibitior	+	0.9148	91.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7635	76.35%
P-glycoprotein inhibitior	-	0.8263	82.63%
P-glycoprotein substrate	-	0.9520	95.20%
CYP3A4 substrate	-	0.5348	53.48%
CYP2C9 substrate	-	0.8009	80.09%
CYP2D6 substrate	-	0.8664	86.64%
CYP3A4 inhibition	-	0.7006	70.06%
CYP2C9 inhibition	+	0.9592	95.92%
CYP2C19 inhibition	+	0.7766	77.66%
CYP2D6 inhibition	-	0.7041	70.41%
CYP1A2 inhibition	+	0.9159	91.59%
CYP2C8 inhibition	-	0.9063	90.63%
CYP inhibitory promiscuity	+	0.8403	84.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8088	80.88%
Carcinogenicity (trinary)	Non-required	0.5102	51.02%
Eye corrosion	-	0.9965	99.65%
Eye irritation	-	0.5199	51.99%
Skin irritation	-	0.5908	59.08%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6596	65.96%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.8430	84.30%
skin sensitisation	-	0.6582	65.82%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5822	58.22%
Acute Oral Toxicity (c)	III	0.4962	49.62%
Estrogen receptor binding	+	0.8735	87.35%
Androgen receptor binding	+	0.7178	71.78%
Thyroid receptor binding	-	0.6146	61.46%
Glucocorticoid receptor binding	+	0.6049	60.49%
Aromatase binding	-	0.5644	56.44%
PPAR gamma	+	0.7337	73.37%
Honey bee toxicity	-	0.9463	94.63%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	96.21%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.07%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.23%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.74%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.07%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.80%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.74%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	80.40%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.30%	90.71%
CHEMBL4208	P20618	Proteasome component C5	80.27%	90.00%

Plants that contains it

• Diospyros batocana
• Diospyros chloroxylon
• Diospyros ismailii
• Diospyros rotundifolia

Cross-Links

• PubChem: 12173109
• LOTUS: LTS0158675
• wikiData: Q104396620