(2S)-2-Prenyl-2beta,3beta-epoxy-1,2,3,4-tetrahydronaphthalene-1,4-dione

Details

• Internal ID: 1a482ac8-7654-4e8d-ab3b-6bf7ebaeb215
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin K compounds
• IUPAC Name: (1aS,7aR)-1a-(3-methylbut-2-enyl)-7aH-naphtho[2,3-b]oxirene-2,7-dione
• SMILES (Canonical): CC(=CCC12C(O1)C(=O)C3=CC=CC=C3C2=O)C
• SMILES (Isomeric): CC(=CC[C@@]12[C@@H](O1)C(=O)C3=CC=CC=C3C2=O)C
• InChI: InChI=1S/C15H14O3/c1-9(2)7-8-15-13(17)11-6-4-3-5-10(11)12(16)14(15)18-15/h3-7,14H,8H2,1-2H3/t14-,15+/m0/s1
• InChI Key: AJPHRWUGXPZXBM-LSDHHAIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.70 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• (2S)-2-Prenyl-2beta,3beta-epoxy-1,2,3,4-tetrahydronaphthalene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7238	72.38%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7205	72.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8917	89.17%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8712	87.12%
P-glycoprotein inhibitior	-	0.9239	92.39%
P-glycoprotein substrate	-	0.9042	90.42%
CYP3A4 substrate	-	0.5416	54.16%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	-	0.7743	77.43%
CYP3A4 inhibition	-	0.7617	76.17%
CYP2C9 inhibition	+	0.5394	53.94%
CYP2C19 inhibition	+	0.6494	64.94%
CYP2D6 inhibition	-	0.7346	73.46%
CYP1A2 inhibition	+	0.5374	53.74%
CYP2C8 inhibition	-	0.8974	89.74%
CYP inhibitory promiscuity	+	0.7421	74.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9118	91.18%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	-	0.9816	98.16%
Eye irritation	+	0.6422	64.22%
Skin irritation	-	0.6459	64.59%
Skin corrosion	-	0.9002	90.02%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6378	63.78%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	+	0.7356	73.56%
skin sensitisation	+	0.5886	58.86%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8421	84.21%
Acute Oral Toxicity (c)	III	0.5009	50.09%
Estrogen receptor binding	-	0.5644	56.44%
Androgen receptor binding	+	0.5378	53.78%
Thyroid receptor binding	-	0.5762	57.62%
Glucocorticoid receptor binding	-	0.6877	68.77%
Aromatase binding	-	0.6931	69.31%
PPAR gamma	+	0.5769	57.69%
Honey bee toxicity	-	0.9196	91.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9820	98.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.18%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.61%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.77%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.83%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.26%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	82.10%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.27%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.87%	89.00%
CHEMBL301	P24941	Cyclin-dependent kinase 2	80.63%	91.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.32%	85.14%

Plants that contains it

• Barleria alluaudii
• Diospyros maritima

Cross-Links

• PubChem: 70691962
• NPASS: NPC62138
• ChEMBL: CHEMBL2023566
• LOTUS: LTS0190361
• wikiData: Q104913319