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

Details

• Internal ID: afb5d80d-b810-4675-bce9-558991cf0378
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-3-[(5-hydroxy-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CC3=CC(=O)C4=C(C3=O)C=CC=C4O
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CC3=CC(=O)C4=C(C3=O)C=CC=C4O
• InChI: InChI=1S/C22H14O6/c1-10-14(22(28)19-13(20(10)26)5-3-7-16(19)24)8-11-9-17(25)18-12(21(11)27)4-2-6-15(18)23/h2-7,9,23-24H,8H2,1H3
• InChI Key: CEBZDZOZLNOOFL-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: 3.70
• Atomic LogP (AlogP): 3.19
• 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	+	0.9968	99.68%
Caco-2	-	0.5612	56.12%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8320	83.20%
OATP2B1 inhibitior	+	0.5675	56.75%
OATP1B1 inhibitior	+	0.9053	90.53%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5716	57.16%
P-glycoprotein inhibitior	-	0.9190	91.90%
P-glycoprotein substrate	-	0.8270	82.70%
CYP3A4 substrate	+	0.5483	54.83%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8456	84.56%
CYP3A4 inhibition	-	0.7979	79.79%
CYP2C9 inhibition	+	0.9404	94.04%
CYP2C19 inhibition	+	0.6756	67.56%
CYP2D6 inhibition	-	0.6264	62.64%
CYP1A2 inhibition	+	0.9163	91.63%
CYP2C8 inhibition	-	0.8473	84.73%
CYP inhibitory promiscuity	+	0.8630	86.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8145	81.45%
Carcinogenicity (trinary)	Non-required	0.5810	58.10%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.6528	65.28%
Skin irritation	+	0.4910	49.10%
Skin corrosion	-	0.9148	91.48%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6213	62.13%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6802	68.02%
skin sensitisation	-	0.5496	54.96%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6653	66.53%
Acute Oral Toxicity (c)	III	0.4475	44.75%
Estrogen receptor binding	+	0.8439	84.39%
Androgen receptor binding	-	0.4894	48.94%
Thyroid receptor binding	-	0.7036	70.36%
Glucocorticoid receptor binding	+	0.7020	70.20%
Aromatase binding	-	0.5350	53.50%
PPAR gamma	+	0.6367	63.67%
Honey bee toxicity	-	0.9410	94.10%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	98.76%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.21%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	90.61%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.07%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.75%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.85%	96.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.41%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	84.67%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.35%	91.11%
CHEMBL2535	P11166	Glucose transporter	82.92%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%

Plants that contains it

• Diospyros maritima
• Plumbago zeylanica

Cross-Links

• PubChem: 100947536
• NPASS: NPC37984
• LOTUS: LTS0242174
• wikiData: Q104955420