[(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]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: df35f17c-1557-471a-96dd-9f1ec3496598
• 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]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C2CC3C(CCC3(C)OC4C(C(C(C(O4)COC(=O)C)O)O)O)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)O)C(=C)C[C@H]2OC1=O
• InChI: InChI=1S/C23H34O9/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/h11,13-20,22,25-27H,1,5-9H2,2-4H3/t11-,13+,14+,15+,16+,17+,18+,19-,20+,22-,23+/m0/s1
• InChI Key: RRZBHFAQTNSANW-LVIVSYKQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₉
• Molecular Weight: 454.50 g/mol
• Exact Mass: 454.22028266 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.69
• 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	+	0.7871	78.71%
Caco-2	-	0.7535	75.35%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8071	80.71%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8132	81.32%
OATP1B3 inhibitior	+	0.9230	92.30%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7521	75.21%
BSEP inhibitior	-	0.7107	71.07%
P-glycoprotein inhibitior	-	0.6328	63.28%
P-glycoprotein substrate	-	0.6503	65.03%
CYP3A4 substrate	+	0.7179	71.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8944	89.44%
CYP3A4 inhibition	-	0.8810	88.10%
CYP2C9 inhibition	-	0.7451	74.51%
CYP2C19 inhibition	-	0.8381	83.81%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.7639	76.39%
CYP2C8 inhibition	+	0.4625	46.25%
CYP inhibitory promiscuity	-	0.9301	93.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6466	64.66%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9590	95.90%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4742	47.42%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6681	66.81%
Acute Oral Toxicity (c)	III	0.4295	42.95%
Estrogen receptor binding	+	0.6592	65.92%
Androgen receptor binding	+	0.6138	61.38%
Thyroid receptor binding	+	0.5447	54.47%
Glucocorticoid receptor binding	+	0.5709	57.09%
Aromatase binding	+	0.5372	53.72%
PPAR gamma	-	0.4938	49.38%
Honey bee toxicity	-	0.6482	64.82%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9886	98.86%

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	97.29%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.26%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.99%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.28%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.18%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.54%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.39%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.83%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	85.70%	92.50%
CHEMBL1937	Q92769	Histone deacetylase 2	84.86%	94.75%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.02%	89.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.39%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.33%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.43%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.35%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.28%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.86%	94.45%

Plants that contains it

• Hymenoxys lemmonii
• Hymenoxys richardsonii

Cross-Links

• PubChem: 14527116
• LOTUS: LTS0059834
• wikiData: Q104396979