[(3S,3aR,4S,6S,6aS,9aS,9bS)-3-acetyloxy-6-hydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R)-2-methylbutanoate

Details

• Internal ID: f766d841-2d46-4be3-a0cc-e98b23ca801c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3S,3aR,4S,6S,6aS,9aS,9bS)-3-acetyloxy-6-hydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2CC=C(C2C3C1C(C(=O)O3)(C)OC(=O)C)C)(C)O
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1C[C@]([C@H]2CC=C([C@H]2[C@H]3[C@@H]1[C@](C(=O)O3)(C)OC(=O)C)C)(C)O
• InChI: InChI=1S/C22H32O7/c1-7-11(2)19(24)27-15-10-21(5,26)14-9-8-12(3)16(14)18-17(15)22(6,20(25)28-18)29-13(4)23/h8,11,14-18,26H,7,9-10H2,1-6H3/t11-,14+,15+,16-,17-,18+,21+,22+/m1/s1
• InChI Key: JOWYYORWZXUMDV-IAFWTCKBSA-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): 2.54
• 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	+	0.9934	99.34%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5350	53.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.9295	92.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6733	67.33%
P-glycoprotein inhibitior	+	0.6669	66.69%
P-glycoprotein substrate	+	0.5092	50.92%
CYP3A4 substrate	+	0.6519	65.19%
CYP2C9 substrate	-	0.8228	82.28%
CYP2D6 substrate	-	0.8756	87.56%
CYP3A4 inhibition	+	0.6163	61.63%
CYP2C9 inhibition	-	0.7026	70.26%
CYP2C19 inhibition	-	0.7020	70.20%
CYP2D6 inhibition	-	0.9576	95.76%
CYP1A2 inhibition	-	0.6897	68.97%
CYP2C8 inhibition	-	0.6343	63.43%
CYP inhibitory promiscuity	-	0.9083	90.83%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5288	52.88%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.9445	94.45%
Skin irritation	-	0.5127	51.27%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5572	55.72%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7316	73.16%
skin sensitisation	-	0.7629	76.29%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4247	42.47%
Estrogen receptor binding	+	0.8098	80.98%
Androgen receptor binding	+	0.6545	65.45%
Thyroid receptor binding	+	0.5730	57.30%
Glucocorticoid receptor binding	+	0.6936	69.36%
Aromatase binding	-	0.5189	51.89%
PPAR gamma	+	0.5787	57.87%
Honey bee toxicity	-	0.7285	72.85%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9770	97.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.48%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.93%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.42%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.43%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.24%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.92%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	88.73%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.19%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.27%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.48%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.18%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.99%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.97%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.93%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.94%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.72%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	81.43%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.16%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162952716
• LOTUS: LTS0148301
• wikiData: Q105132571