5-Hydroxy-3-(4-hydroxy-7-methyl-5,8-dioxonaphthalen-1-yl)-2-methylnaphthalene-1,4-dione

Details

• Internal ID: e24584cf-79f9-463b-bb80-3b3b8e1f7349
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-3-(4-hydroxy-7-methyl-5,8-dioxonaphthalen-1-yl)-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(C=CC(=C2C1=O)C3=C(C(=O)C4=C(C3=O)C(=CC=C4)O)C)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=CC(=C2C1=O)C3=C(C(=O)C4=C(C3=O)C(=CC=C4)O)C)O
• InChI: InChI=1S/C22H14O6/c1-9-8-15(25)19-14(24)7-6-11(18(19)20(9)26)16-10(2)21(27)12-4-3-5-13(23)17(12)22(16)28/h3-8,23-24H,1-2H3
• InChI Key: CKYANOPNBSDDHH-UHFFFAOYSA-N
• Popularity: 2 references 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: 3.80
• Atomic LogP (AlogP): 3.28
• 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	+	0.6332	63.32%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.9018	90.18%
OATP2B1 inhibitior	+	0.5737	57.37%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.9148	91.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6987	69.87%
P-glycoprotein inhibitior	-	0.8415	84.15%
P-glycoprotein substrate	-	0.8436	84.36%
CYP3A4 substrate	+	0.5203	52.03%
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	-	0.7618	76.18%
CYP inhibitory promiscuity	+	0.8403	84.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8088	80.88%
Carcinogenicity (trinary)	Non-required	0.5102	51.02%
Eye corrosion	-	0.9965	99.65%
Eye irritation	+	0.5847	58.47%
Skin irritation	-	0.5908	59.08%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6582	65.82%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.6582	65.82%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6895	68.95%
Acute Oral Toxicity (c)	III	0.4962	49.62%
Estrogen receptor binding	+	0.7547	75.47%
Androgen receptor binding	+	0.6991	69.91%
Thyroid receptor binding	-	0.7458	74.58%
Glucocorticoid receptor binding	+	0.6554	65.54%
Aromatase binding	-	0.7254	72.54%
PPAR gamma	+	0.6620	66.20%
Honey bee toxicity	-	0.9227	92.27%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL1951	P21397	Monoamine oxidase A	98.43%	91.49%
CHEMBL2581	P07339	Cathepsin D	98.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.21%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.94%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.12%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	91.18%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.56%	91.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.84%	96.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.57%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	88.16%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.03%	89.00%
CHEMBL2535	P11166	Glucose transporter	81.24%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.28%	86.33%

Plants that contains it

• Diospyros chloroxylon
• Diospyros maritima

Cross-Links

• PubChem: 12232585
• NPASS: NPC101870
• LOTUS: LTS0090275
• wikiData: Q104963012