Leopersin L

Details

• Internal ID: 81161a77-68dc-4588-9db4-9899de321357
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4R)-4-[2-[(4S,4aS,8aS)-4-hydroxy-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-4-hydroxyoxolan-2-one
• SMILES (Canonical): CC1=C(C2(CCCC(C2C(C1=O)O)(C)C)C)CCC3(CC(=O)OC3)O
• SMILES (Isomeric): CC1=C([C@]2(CCCC([C@@H]2[C@@H](C1=O)O)(C)C)C)CC[C@]3(CC(=O)OC3)O
• InChI: InChI=1S/C20H30O5/c1-12-13(6-9-20(24)10-14(21)25-11-20)19(4)8-5-7-18(2,3)17(19)16(23)15(12)22/h16-17,23-24H,5-11H2,1-4H3/t16-,17+,19-,20-/m1/s1
• InChI Key: FCPONUSIIXWZOQ-PIKOESSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	+	0.6656	66.56%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8437	84.37%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8798	87.98%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5495	54.95%
BSEP inhibitior	+	0.6541	65.41%
P-glycoprotein inhibitior	-	0.7399	73.99%
P-glycoprotein substrate	-	0.7091	70.91%
CYP3A4 substrate	+	0.6173	61.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9053	90.53%
CYP3A4 inhibition	-	0.6707	67.07%
CYP2C9 inhibition	-	0.7893	78.93%
CYP2C19 inhibition	-	0.9040	90.40%
CYP2D6 inhibition	-	0.9530	95.30%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	-	0.6783	67.83%
CYP inhibitory promiscuity	-	0.9040	90.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4820	48.20%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.7725	77.25%
Skin irritation	+	0.6533	65.33%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5786	57.86%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.8832	88.32%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6636	66.36%
Acute Oral Toxicity (c)	III	0.4667	46.67%
Estrogen receptor binding	+	0.6880	68.80%
Androgen receptor binding	+	0.5788	57.88%
Thyroid receptor binding	+	0.5191	51.91%
Glucocorticoid receptor binding	+	0.8142	81.42%
Aromatase binding	+	0.6214	62.14%
PPAR gamma	+	0.6459	64.59%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.13%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.52%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.17%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.01%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.93%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.00%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.99%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.70%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.30%	94.75%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.24%	86.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.75%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.69%	96.77%

Plants that contains it

• Leonurus persicus

Cross-Links

• PubChem: 102427310
• NPASS: NPC163448