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

Details

• Internal ID: 07a44c13-ff9a-4a6d-be96-94c143599911
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,2S,3R,4S,4aS,8aR)-2-[(2R)-2-acetyloxy-3-methylbutanoyl]oxy-3-hydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-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)(C)O)OC(=O)C(C(C)C)OC(=O)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=C/C3=CC(=O)OC3)(C)O)OC(=O)[C@@H](C(C)C)OC(=O)C)OC(=O)C4=CN=CC=C4)C
• InChI: InChI=1S/C33H41NO9/c1-19(2)26(41-21(4)35)30(38)43-28-27(42-29(37)23-11-9-15-34-17-23)32(6)20(3)10-8-12-24(32)31(5,33(28,7)39)14-13-22-16-25(36)40-18-22/h9-11,13-17,19,24,26-28,39H,8,12,18H2,1-7H3/b14-13+/t24-,26-,27+,28+,31+,32+,33+/m1/s1
• InChI Key: QLQRVRCHRRIMMB-VYEVJRMJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₁NO₉
• Molecular Weight: 595.70 g/mol
• Exact Mass: 595.27813189 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.28
• 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	+	0.9552	95.52%
Caco-2	-	0.7854	78.54%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8003	80.03%
OATP2B1 inhibitior	-	0.5770	57.70%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.8851	88.51%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9748	97.48%
P-glycoprotein inhibitior	+	0.8904	89.04%
P-glycoprotein substrate	+	0.6180	61.80%
CYP3A4 substrate	+	0.6934	69.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9083	90.83%
CYP3A4 inhibition	-	0.5206	52.06%
CYP2C9 inhibition	-	0.6582	65.82%
CYP2C19 inhibition	-	0.6675	66.75%
CYP2D6 inhibition	-	0.8539	85.39%
CYP1A2 inhibition	+	0.6469	64.69%
CYP2C8 inhibition	+	0.8241	82.41%
CYP inhibitory promiscuity	+	0.5702	57.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4426	44.26%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9234	92.34%
Skin irritation	-	0.7042	70.42%
Skin corrosion	-	0.9171	91.71%
Ames mutagenesis	-	0.5256	52.56%
Human Ether-a-go-go-Related Gene inhibition	-	0.4620	46.20%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6502	65.02%
skin sensitisation	-	0.7839	78.39%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4927	49.27%
Acute Oral Toxicity (c)	III	0.5752	57.52%
Estrogen receptor binding	+	0.7537	75.37%
Androgen receptor binding	+	0.7195	71.95%
Thyroid receptor binding	+	0.6524	65.24%
Glucocorticoid receptor binding	+	0.8043	80.43%
Aromatase binding	+	0.6223	62.23%
PPAR gamma	+	0.6742	67.42%
Honey bee toxicity	-	0.7616	76.16%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9170	91.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.39%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.13%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.18%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.06%	85.14%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	93.19%	85.30%
CHEMBL2535	P11166	Glucose transporter	92.28%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.83%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.35%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.01%	98.75%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.53%	83.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.90%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.32%	95.71%
CHEMBL1951	P21397	Monoamine oxidase A	88.25%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.24%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.24%	93.56%
CHEMBL3524	P56524	Histone deacetylase 4	87.83%	92.97%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.96%	94.80%
CHEMBL5028	O14672	ADAM10	86.94%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	86.57%	97.79%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.88%	96.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.86%	97.47%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.44%	81.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.35%	93.40%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.76%	88.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.27%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.01%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.79%	97.09%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	80.46%	92.95%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.23%	100.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.22%	87.67%

Plants that contains it

• Scutellaria barbata

Cross-Links

• PubChem: 162929054
• LOTUS: LTS0050116
• wikiData: Q105223734