2-[5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)-1,4-dioxo-3H-naphthalen-2-yl]acetic acid

Details

• Internal ID: 8d48574e-4027-4c9a-9a32-0ddb9918092f
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 2-[5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)-1,4-dioxo-3H-naphthalen-2-yl]acetic acid
• InChI: InChI=1S/C18H20O7/c1-9(2)3-6-13(22)18(8-14(23)24)7-12(21)15-10(19)4-5-11(20)16(15)17(18)25/h3-5,13,19-20,22H,6-8H2,1-2H3,(H,23,24)
• InChI Key: DXDKUSNRUQYNHG-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₇
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.12090297 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	-	0.5984	59.84%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8584	85.84%
OATP2B1 inhibitior	-	0.7057	70.57%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8773	87.73%
P-glycoprotein inhibitior	-	0.9285	92.85%
P-glycoprotein substrate	-	0.8395	83.95%
CYP3A4 substrate	-	0.5097	50.97%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.8190	81.90%
CYP2C9 inhibition	-	0.6194	61.94%
CYP2C19 inhibition	-	0.6240	62.40%
CYP2D6 inhibition	-	0.7913	79.13%
CYP1A2 inhibition	-	0.6845	68.45%
CYP2C8 inhibition	-	0.8740	87.40%
CYP inhibitory promiscuity	-	0.6682	66.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8635	86.35%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.6368	63.68%
Skin corrosion	-	0.9093	90.93%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7681	76.81%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.5387	53.87%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7029	70.29%
Acute Oral Toxicity (c)	III	0.5162	51.62%
Estrogen receptor binding	-	0.5572	55.72%
Androgen receptor binding	+	0.6960	69.60%
Thyroid receptor binding	-	0.6249	62.49%
Glucocorticoid receptor binding	+	0.6897	68.97%
Aromatase binding	-	0.6003	60.03%
PPAR gamma	+	0.6269	62.69%
Honey bee toxicity	-	0.8970	89.70%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.94%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.79%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.54%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.16%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.65%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.67%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.66%	89.00%
CHEMBL4208	P20618	Proteasome component C5	85.94%	90.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.62%	85.30%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.84%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.31%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	80.16%	91.19%

Plants that contains it

• Arnebia hispidissima

Cross-Links

• PubChem: 56842723
• LOTUS: LTS0001106
• wikiData: Q104394945