[(2R,3S,4S,5R,6S)-6-[[(1S,3aR,5aS,8R,8aR,9aR)-1,8-dimethyl-5-methylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydro-1H-azuleno[6,7-b]furan-8-yl]oxy]-5-acetyloxy-3,4-dihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 1a31fe7d-5c40-404c-8785-e61c81364510
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[[(1S,3aR,5aS,8R,8aR,9aR)-1,8-dimethyl-5-methylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydro-1H-azuleno[6,7-b]furan-8-yl]oxy]-5-acetyloxy-3,4-dihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C2CC3C(CCC3(C)OC4C(C(C(C(O4)COC(=O)C)O)O)OC(=O)C)C(=C)CC2OC1=O
• SMILES (Isomeric): C[C@H]1[C@H]2C[C@@H]3[C@H](CC[C@@]3(C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C)O)O)OC(=O)C)C(=C)C[C@H]2OC1=O
• InChI: InChI=1S/C25H36O10/c1-11-8-18-16(12(2)23(30)33-18)9-17-15(11)6-7-25(17,5)35-24-22(32-14(4)27)21(29)20(28)19(34-24)10-31-13(3)26/h12,15-22,24,28-29H,1,6-10H2,2-5H3/t12-,15+,16+,17+,18+,19+,20+,21-,22+,24-,25+/m0/s1
• InChI Key: NGVOSVJBMPZFNB-XDZZORAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₁₀
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.23084734 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.26
• 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	+	0.8850	88.50%
Caco-2	-	0.7628	76.28%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8394	83.94%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.7853	78.53%
OATP1B3 inhibitior	+	0.9047	90.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7771	77.71%
BSEP inhibitior	+	0.6339	63.39%
P-glycoprotein inhibitior	-	0.4618	46.18%
P-glycoprotein substrate	-	0.5959	59.59%
CYP3A4 substrate	+	0.7252	72.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8944	89.44%
CYP3A4 inhibition	-	0.8067	80.67%
CYP2C9 inhibition	-	0.7276	72.76%
CYP2C19 inhibition	-	0.8169	81.69%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.6801	68.01%
CYP2C8 inhibition	+	0.4780	47.80%
CYP inhibitory promiscuity	-	0.9412	94.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6098	60.98%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9425	94.25%
Skin irritation	+	0.5358	53.58%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5918	59.18%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8997	89.97%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6650	66.50%
Acute Oral Toxicity (c)	III	0.4103	41.03%
Estrogen receptor binding	+	0.7360	73.60%
Androgen receptor binding	+	0.6423	64.23%
Thyroid receptor binding	-	0.5111	51.11%
Glucocorticoid receptor binding	+	0.6525	65.25%
Aromatase binding	+	0.5988	59.88%
PPAR gamma	+	0.5816	58.16%
Honey bee toxicity	-	0.6334	63.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.60%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.42%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.10%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.22%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	90.93%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	90.52%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	89.83%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.23%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.17%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.58%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.38%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	85.69%	97.79%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.10%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.48%	93.04%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.42%	96.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.02%	94.80%
CHEMBL1937	Q92769	Histone deacetylase 2	81.21%	94.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.19%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.11%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.89%	90.08%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.34%	95.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.31%	82.50%

Plants that contains it

• Geigeria ornativa

Cross-Links

• PubChem: 163186789
• LOTUS: LTS0049258
• wikiData: Q105179213