[(4S,4aR,5S,6R,8aR,9aR)-6-acetyloxy-8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate

Details

• Internal ID: fa18bcb8-a531-4ea7-b20a-b70d488e5e0e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aR,5S,6R,8aR,9aR)-6-acetyloxy-8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2=C(C(=O)OC2CC3(C1(C(C(CC3)OC(=O)C)C)C)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1C2=C(C(=O)O[C@@H]2C[C@]3([C@@]1([C@@H]([C@@H](CC3)OC(=O)C)C)C)O)C
• InChI: InChI=1S/C22H32O7/c1-7-11(2)19(24)29-18-17-12(3)20(25)28-16(17)10-22(26)9-8-15(27-14(5)23)13(4)21(18,22)6/h11,13,15-16,18,26H,7-10H2,1-6H3/t11-,13-,15-,16-,18+,21-,22-/m1/s1
• InChI Key: NQUDNNNRNDPWFZ-KDGZLGQYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₇
• Molecular Weight: 408.50 g/mol
• Exact Mass: 408.21480336 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.6085	60.85%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6986	69.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8550	85.50%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6602	66.02%
P-glycoprotein inhibitior	+	0.6312	63.12%
P-glycoprotein substrate	-	0.6189	61.89%
CYP3A4 substrate	+	0.6670	66.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9170	91.70%
CYP3A4 inhibition	+	0.6820	68.20%
CYP2C9 inhibition	-	0.7506	75.06%
CYP2C19 inhibition	-	0.8670	86.70%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	-	0.7997	79.97%
CYP2C8 inhibition	-	0.7962	79.62%
CYP inhibitory promiscuity	-	0.7714	77.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5248	52.48%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9116	91.16%
Skin irritation	+	0.6298	62.98%
Skin corrosion	-	0.8901	89.01%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5698	56.98%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6268	62.68%
skin sensitisation	-	0.8343	83.43%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6927	69.27%
Acute Oral Toxicity (c)	III	0.4929	49.29%
Estrogen receptor binding	+	0.8639	86.39%
Androgen receptor binding	+	0.6476	64.76%
Thyroid receptor binding	+	0.5235	52.35%
Glucocorticoid receptor binding	+	0.8235	82.35%
Aromatase binding	+	0.5825	58.25%
PPAR gamma	+	0.6889	68.89%
Honey bee toxicity	-	0.8053	80.53%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5388	53.88%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.93%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.76%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.41%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.16%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.38%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.31%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.59%	94.80%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.23%	96.47%
CHEMBL2996	Q05655	Protein kinase C delta	88.66%	97.79%
CHEMBL4072	P07858	Cathepsin B	87.52%	93.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.83%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.38%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.19%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.19%	85.14%
CHEMBL3837	P07711	Cathepsin L	84.57%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.64%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	82.33%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.51%	97.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.33%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.12%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.66%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.59%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.06%	91.07%

Plants that contains it

• Ligularia japonica

Cross-Links

• PubChem: 163024420
• LOTUS: LTS0110483
• wikiData: Q105184079