[(2R,3R,4S,5R,6S)-6-[[(3aR,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]-4-acetyloxy-3,5-dihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 5382b25b-1ae7-46a9-9fda-efa8a21b12f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-[[(3aR,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]-4-acetyloxy-3,5-dihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)OC(=O)C)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)OC(=O)C)O
• InChI: InChI=1S/C25H34O10/c1-11-8-18-16(12(2)23(30)33-18)9-17-15(11)6-7-25(17,5)35-24-21(29)22(32-14(4)27)20(28)19(34-24)10-31-13(3)26/h15-22,24,28-29H,1-2,6-10H2,3-5H3/t15-,16-,17-,18-,19-,20-,21-,22+,24+,25-/m1/s1
• InChI Key: SWLAMBRETNNVQF-KUMDYOAKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₁₀
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.21519728 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9262	92.62%
Caco-2	-	0.8069	80.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7906	79.06%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.7915	79.15%
OATP1B3 inhibitior	+	0.9116	91.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7636	76.36%
BSEP inhibitior	-	0.6026	60.26%
P-glycoprotein inhibitior	-	0.4413	44.13%
P-glycoprotein substrate	-	0.6692	66.92%
CYP3A4 substrate	+	0.7170	71.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8994	89.94%
CYP3A4 inhibition	-	0.8497	84.97%
CYP2C9 inhibition	-	0.7897	78.97%
CYP2C19 inhibition	-	0.9000	90.00%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.8086	80.86%
CYP2C8 inhibition	+	0.5225	52.25%
CYP inhibitory promiscuity	-	0.9170	91.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6481	64.81%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9240	92.40%
Skin irritation	-	0.5438	54.38%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4482	44.82%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8853	88.53%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4559	45.59%
Acute Oral Toxicity (c)	III	0.3989	39.89%
Estrogen receptor binding	+	0.6646	66.46%
Androgen receptor binding	+	0.6979	69.79%
Thyroid receptor binding	-	0.5526	55.26%
Glucocorticoid receptor binding	+	0.6703	67.03%
Aromatase binding	+	0.6524	65.24%
PPAR gamma	+	0.5638	56.38%
Honey bee toxicity	-	0.6532	65.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9857	98.57%

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	97.10%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.78%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.05%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.78%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.47%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	90.79%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	88.40%	97.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.23%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	87.90%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	87.22%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.81%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.68%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.03%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.67%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.36%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.45%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.95%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.38%	94.00%
CHEMBL5957	P21589	5'-nucleotidase	80.25%	97.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.20%	86.33%

Plants that contains it

• Hymenoxys richardsonii

Cross-Links

• PubChem: 101927622
• LOTUS: LTS0005583
• wikiData: Q105262737