[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] benzoate

Details

• Internal ID: c609ed86-b1e8-42e7-9785-0bd6bcaa8f73
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] benzoate
• SMILES (Canonical): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C3=CC=CC=C3)C
• SMILES (Isomeric): CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C3=CC=CC=C3)C
• InChI: InChI=1S/C23H20O6/c1-13(2)8-11-19(29-23(28)14-6-4-3-5-7-14)15-12-18(26)20-16(24)9-10-17(25)21(20)22(15)27/h3-10,12,19,24-25H,11H2,1-2H3/t19-/m1/s1
• InChI Key: ICTJEGSRKSUYCN-LJQANCHMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₆
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.12598835 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 3.99
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	-	0.7062	70.62%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8716	87.16%
OATP2B1 inhibitior	-	0.7233	72.33%
OATP1B1 inhibitior	+	0.9217	92.17%
OATP1B3 inhibitior	+	0.8871	88.71%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6806	68.06%
P-glycoprotein inhibitior	-	0.4670	46.70%
P-glycoprotein substrate	-	0.8917	89.17%
CYP3A4 substrate	+	0.5217	52.17%
CYP2C9 substrate	-	0.7821	78.21%
CYP2D6 substrate	-	0.8836	88.36%
CYP3A4 inhibition	-	0.8415	84.15%
CYP2C9 inhibition	+	0.8748	87.48%
CYP2C19 inhibition	+	0.7450	74.50%
CYP2D6 inhibition	+	0.5245	52.45%
CYP1A2 inhibition	+	0.7381	73.81%
CYP2C8 inhibition	+	0.4438	44.38%
CYP inhibitory promiscuity	+	0.7103	71.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8615	86.15%
Carcinogenicity (trinary)	Non-required	0.6523	65.23%
Eye corrosion	-	0.9950	99.50%
Eye irritation	-	0.6488	64.88%
Skin irritation	-	0.7881	78.81%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4725	47.25%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	+	0.5535	55.35%
skin sensitisation	-	0.6522	65.22%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6222	62.22%
Acute Oral Toxicity (c)	III	0.6513	65.13%
Estrogen receptor binding	+	0.7496	74.96%
Androgen receptor binding	+	0.7655	76.55%
Thyroid receptor binding	-	0.5498	54.98%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	-	0.6072	60.72%
PPAR gamma	+	0.7397	73.97%
Honey bee toxicity	-	0.8886	88.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	97.78%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.51%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.23%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.69%	86.33%
CHEMBL240	Q12809	HERG	88.18%	89.76%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.78%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	87.36%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	83.14%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.27%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.71%	99.17%

Plants that contains it

• Lithospermum erythrorhizon

Cross-Links

• PubChem: 10475609
• LOTUS: LTS0260836
• wikiData: Q105111153