Leoheteronin B

Details

• Internal ID: 73e360ed-edda-4cda-92d1-0d3b8cbdb07e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• SMILES (Canonical): CC1=C(C2(CCCC(C2CC1=O)(C)C)C)CCC3=CCOC3=O
• SMILES (Isomeric): CC1=C([C@]2(CCCC([C@@H]2CC1=O)(C)C)C)CCC3=CCOC3=O
• InChI: InChI=1S/C20H28O3/c1-13-15(7-6-14-8-11-23-18(14)22)20(4)10-5-9-19(2,3)17(20)12-16(13)21/h8,17H,5-7,9-12H2,1-4H3/t17-,20+/m0/s1
• InChI Key: MOSHRBDKOZMXHA-FXAWDEMLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• CHEMBL4750085

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.7227	72.27%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8294	82.94%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8534	85.34%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	+	0.6944	69.44%
P-glycoprotein inhibitior	-	0.4770	47.70%
P-glycoprotein substrate	-	0.8141	81.41%
CYP3A4 substrate	+	0.5897	58.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.7340	73.40%
CYP2C9 inhibition	-	0.8262	82.62%
CYP2C19 inhibition	-	0.6823	68.23%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.7780	77.80%
CYP2C8 inhibition	-	0.6610	66.10%
CYP inhibitory promiscuity	-	0.6961	69.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5709	57.09%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.7749	77.49%
Skin irritation	-	0.5933	59.33%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6672	66.72%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5187	51.87%
Acute Oral Toxicity (c)	III	0.7660	76.60%
Estrogen receptor binding	-	0.4938	49.38%
Androgen receptor binding	+	0.5965	59.65%
Thyroid receptor binding	+	0.5381	53.81%
Glucocorticoid receptor binding	+	0.6960	69.60%
Aromatase binding	+	0.5500	55.00%
PPAR gamma	+	0.7496	74.96%
Honey bee toxicity	-	0.8502	85.02%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9964	99.64%

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	96.21%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.86%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.51%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.21%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.14%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.24%	94.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.37%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.03%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.74%	86.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.40%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.85%	94.45%

Plants that contains it

• Leonurus japonicus

Cross-Links

• PubChem: 11370504
• NPASS: NPC294955
• LOTUS: LTS0256532
• wikiData: Q105169116