[(1R,2S,3R,4S,4aS,8aR)-4-[(1S)-1-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2-(2-methylpropanoyloxy)-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate

Details

• Internal ID: 10f75513-c0e9-492a-84ab-05917524f8c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,2S,3R,4S,4aS,8aR)-4-[(1S)-1-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-3-hydroxy-3,4,8,8a-tetramethyl-2-(2-methylpropanoyloxy)-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC1=CCCC2C1(C(C(C(C2(C)C(CC3=CC(=O)OC3)OC(=O)C)(C)O)OC(=O)C(C)C)OC(=O)C4=CN=CC=C4)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1([C@H]([C@@H]([C@]([C@]2(C)[C@H](CC3=CC(=O)OC3)OC(=O)C)(C)O)OC(=O)C(C)C)OC(=O)C4=CN=CC=C4)C
• InChI: InChI=1S/C32H41NO9/c1-18(2)28(36)42-27-26(41-29(37)22-11-9-13-33-16-22)30(5)19(3)10-8-12-23(30)31(6,32(27,7)38)24(40-20(4)34)14-21-15-25(35)39-17-21/h9-11,13,15-16,18,23-24,26-27,38H,8,12,14,17H2,1-7H3/t23-,24-,26-,27-,30-,31-,32-/m0/s1
• InChI Key: OIKGYJRBMDIBAR-DWRAXSAJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₁NO₉
• Molecular Weight: 583.70 g/mol
• Exact Mass: 583.27813189 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9499	94.99%
Caco-2	-	0.7624	76.24%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8462	84.62%
OATP2B1 inhibitior	-	0.7172	71.72%
OATP1B1 inhibitior	+	0.8655	86.55%
OATP1B3 inhibitior	+	0.8098	80.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9880	98.80%
P-glycoprotein inhibitior	+	0.8825	88.25%
P-glycoprotein substrate	+	0.6122	61.22%
CYP3A4 substrate	+	0.6896	68.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9084	90.84%
CYP3A4 inhibition	-	0.6395	63.95%
CYP2C9 inhibition	-	0.7579	75.79%
CYP2C19 inhibition	-	0.7846	78.46%
CYP2D6 inhibition	-	0.9008	90.08%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.8167	81.67%
CYP inhibitory promiscuity	-	0.5053	50.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4934	49.34%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.7043	70.43%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5526	55.26%
Human Ether-a-go-go-Related Gene inhibition	+	0.6448	64.48%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6324	63.24%
skin sensitisation	-	0.8219	82.19%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5208	52.08%
Acute Oral Toxicity (c)	III	0.5519	55.19%
Estrogen receptor binding	+	0.7679	76.79%
Androgen receptor binding	+	0.7051	70.51%
Thyroid receptor binding	+	0.6197	61.97%
Glucocorticoid receptor binding	+	0.7954	79.54%
Aromatase binding	+	0.6811	68.11%
PPAR gamma	+	0.7423	74.23%
Honey bee toxicity	-	0.7463	74.63%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9111	91.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.20%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.51%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.35%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	95.68%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.67%	86.33%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	94.83%	85.30%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.69%	99.23%
CHEMBL2535	P11166	Glucose transporter	93.59%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.13%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.05%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.00%	91.07%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.78%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.25%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.56%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.45%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.23%	89.00%
CHEMBL5028	O14672	ADAM10	84.91%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.76%	92.62%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.74%	96.67%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.41%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.33%	96.77%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.69%	83.00%
CHEMBL3524	P56524	Histone deacetylase 4	82.45%	92.97%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.58%	94.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.37%	88.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.30%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.81%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.40%	90.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.35%	98.75%

Plants that contains it

• Scutellaria barbata

Cross-Links

• PubChem: 122177460
• LOTUS: LTS0087698
• wikiData: Q105192553