1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-

Details

• Internal ID: 78a67c88-b93b-4cf4-bd7f-f98810050d5d
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5,8-dihydroxy-6-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
• SMILES (Canonical): CC(=CCC(C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O)O)C
• SMILES (Isomeric): CC(=CCC(C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O)O)C
• InChI: InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17,20-21H,4H2,1-2H3
• InChI Key: UNNKKUDWEASWDN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29 g/mol
• Exact Mass: 288.09977361 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• PD137693

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	+	0.5739	57.39%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7247	72.47%
OATP2B1 inhibitior	-	0.5743	57.43%
OATP1B1 inhibitior	+	0.9119	91.19%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	-	0.8038	80.38%
P-glycoprotein inhibitior	-	0.8767	87.67%
P-glycoprotein substrate	-	0.8937	89.37%
CYP3A4 substrate	-	0.5181	51.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8435	84.35%
CYP3A4 inhibition	+	0.5877	58.77%
CYP2C9 inhibition	+	0.8414	84.14%
CYP2C19 inhibition	+	0.7165	71.65%
CYP2D6 inhibition	+	0.5882	58.82%
CYP1A2 inhibition	+	0.8124	81.24%
CYP2C8 inhibition	-	0.9485	94.85%
CYP inhibitory promiscuity	+	0.8182	81.82%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8922	89.22%
Carcinogenicity (trinary)	Non-required	0.6820	68.20%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.6476	64.76%
Skin irritation	-	0.6323	63.23%
Skin corrosion	-	0.8749	87.49%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5586	55.86%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	+	0.5199	51.99%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7461	74.61%
Acute Oral Toxicity (c)	III	0.7128	71.28%
Estrogen receptor binding	+	0.6585	65.85%
Androgen receptor binding	-	0.5482	54.82%
Thyroid receptor binding	-	0.6282	62.82%
Glucocorticoid receptor binding	+	0.7700	77.00%
Aromatase binding	+	0.6213	62.13%
PPAR gamma	+	0.6997	69.97%
Honey bee toxicity	-	0.9393	93.93%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	+	0.9927	99.27%

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	98.75%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.27%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.06%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.19%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.35%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.20%	96.09%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.02%	83.10%
CHEMBL4208	P20618	Proteasome component C5	84.93%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.84%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.12%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.03%	93.40%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.65%	97.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.62%	95.64%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.12%	89.34%

Plants that contains it

• Arnebia speciosa

Cross-Links

• PubChem: 149437686
• LOTUS: LTS0129369
• wikiData: Q105276064