[(2R,3S,4S,5R,6S)-6-[[(3aS,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 84bd1161-2e1d-4a39-b619-702abaaebf8f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[[(3aS,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@]2(CC[C@H]3[C@H]2C[C@H]4[C@H](CC3=C)OC(=O)C4=C)C)O)O)O
• InChI: InChI=1S/C23H32O9/c1-10-7-16-14(11(2)21(28)30-16)8-15-13(10)5-6-23(15,4)32-22-20(27)19(26)18(25)17(31-22)9-29-12(3)24/h13-20,22,25-27H,1-2,5-9H2,3-4H3/t13-,14-,15-,16+,17-,18-,19+,20-,22+,23-/m1/s1
• InChI Key: ZFGCXKKWHJYYDK-KEGMCWRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₉
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.20463259 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7752	77.52%
Caco-2	-	0.7759	77.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8322	83.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7935	79.35%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7521	75.21%
BSEP inhibitior	-	0.7687	76.87%
P-glycoprotein inhibitior	-	0.6349	63.49%
P-glycoprotein substrate	-	0.7538	75.38%
CYP3A4 substrate	+	0.7011	70.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8996	89.96%
CYP3A4 inhibition	-	0.8993	89.93%
CYP2C9 inhibition	-	0.7920	79.20%
CYP2C19 inhibition	-	0.8602	86.02%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.7807	78.07%
CYP2C8 inhibition	+	0.5122	51.22%
CYP inhibitory promiscuity	-	0.9284	92.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6639	66.39%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9396	93.96%
Skin irritation	-	0.5445	54.45%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4672	46.72%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8867	88.67%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5760	57.60%
Acute Oral Toxicity (c)	III	0.3941	39.41%
Estrogen receptor binding	+	0.6333	63.33%
Androgen receptor binding	+	0.6784	67.84%
Thyroid receptor binding	+	0.5133	51.33%
Glucocorticoid receptor binding	+	0.5704	57.04%
Aromatase binding	+	0.5760	57.60%
PPAR gamma	+	0.5180	51.80%
Honey bee toxicity	-	0.6847	68.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9890	98.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.47%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.40%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.12%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.84%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.82%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.46%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.11%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.81%	92.50%
CHEMBL5957	P21589	5'-nucleotidase	82.51%	97.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.21%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.05%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	81.98%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.98%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.59%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.52%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.28%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.97%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	80.95%	94.75%

Plants that contains it

• Hymenoxys lemmonii

Cross-Links

• PubChem: 162944963
• LOTUS: LTS0180940
• wikiData: Q105374121