Leojaponin

Details

• Internal ID: 329138d3-7a83-4375-b725-aab37ac34787
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR)-4-[2-(furan-3-yl)ethyl]-1-hydroxy-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
• SMILES (Canonical): CC1=C(C2(CCCC(C2=C(C1=O)O)(C)C)C)CCC3=COC=C3
• SMILES (Isomeric): CC1=C([C@]2(CCCC(C2=C(C1=O)O)(C)C)C)CCC3=COC=C3
• InChI: InChI=1S/C20H26O3/c1-13-15(7-6-14-8-11-23-12-14)20(4)10-5-9-19(2,3)18(20)17(22)16(13)21/h8,11-12,22H,5-7,9-10H2,1-4H3/t20-/m1/s1
• InChI Key: OOJGVMFNPNJNFV-HXUWFJFHSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.18819469 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.14
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 864817-63-0
• (4aR)-4-[2-(furan-3-yl)ethyl]-1-hydroxy-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
• CHEMBL4753034
• AKOS040761979

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.7616	76.16%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6754	67.54%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	-	0.3967	39.67%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8390	83.90%
P-glycoprotein inhibitior	-	0.6243	62.43%
P-glycoprotein substrate	-	0.7792	77.92%
CYP3A4 substrate	+	0.6031	60.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8589	85.89%
CYP3A4 inhibition	+	0.6382	63.82%
CYP2C9 inhibition	-	0.6098	60.98%
CYP2C19 inhibition	+	0.5375	53.75%
CYP2D6 inhibition	-	0.8269	82.69%
CYP1A2 inhibition	+	0.6582	65.82%
CYP2C8 inhibition	-	0.6347	63.47%
CYP inhibitory promiscuity	+	0.6905	69.05%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5276	52.76%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.6343	63.43%
Skin irritation	-	0.5369	53.69%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7152	71.52%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5709	57.09%
skin sensitisation	-	0.6848	68.48%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6313	63.13%
Acute Oral Toxicity (c)	III	0.6500	65.00%
Estrogen receptor binding	+	0.7349	73.49%
Androgen receptor binding	+	0.5834	58.34%
Thyroid receptor binding	+	0.6555	65.55%
Glucocorticoid receptor binding	+	0.7946	79.46%
Aromatase binding	+	0.6703	67.03%
PPAR gamma	+	0.8044	80.44%
Honey bee toxicity	-	0.9010	90.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.62%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.49%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.93%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.03%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.14%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.87%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.55%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.20%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.77%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.15%	99.23%

Plants that contains it

• Leonurus japonicus

Cross-Links

• PubChem: 12187536
• NPASS: NPC5745
• LOTUS: LTS0199834
• wikiData: Q105195404