[(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate

Details

• Internal ID: a9efe8e8-518f-4b7a-912a-76480ab493a6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC(C)[C@H](C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H36O11/c1-9(2)19(28)25(33)34-15-6-10(3)13-7-14(11(4)17(13)23-18(15)12(5)24(32)37-23)35-26-22(31)21(30)20(29)16(8-27)36-26/h9,13-23,26-31H,3-8H2,1-2H3/t13-,14-,15+,16+,17-,18+,19+,20+,21-,22+,23+,26+/m0/s1
• InChI Key: HLZBRVYCKXUHSB-FTTCLZOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₁
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.22576196 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.65
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6360	63.60%
Caco-2	-	0.8525	85.25%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7901	79.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8282	82.82%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5697	56.97%
P-glycoprotein inhibitior	-	0.5682	56.82%
P-glycoprotein substrate	-	0.5532	55.32%
CYP3A4 substrate	+	0.6723	67.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8925	89.25%
CYP3A4 inhibition	-	0.8353	83.53%
CYP2C9 inhibition	-	0.8358	83.58%
CYP2C19 inhibition	-	0.8231	82.31%
CYP2D6 inhibition	-	0.9096	90.96%
CYP1A2 inhibition	-	0.8778	87.78%
CYP2C8 inhibition	-	0.6555	65.55%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6992	69.92%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.7594	75.94%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4769	47.69%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.6268	62.68%
skin sensitisation	-	0.8340	83.40%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5557	55.57%
Acute Oral Toxicity (c)	III	0.5098	50.98%
Estrogen receptor binding	+	0.6941	69.41%
Androgen receptor binding	+	0.6314	63.14%
Thyroid receptor binding	-	0.5285	52.85%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5360	53.60%
PPAR gamma	+	0.5565	55.65%
Honey bee toxicity	-	0.6324	63.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9275	92.75%

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	98.76%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	97.44%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.57%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.37%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.02%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.73%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	89.63%	90.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.47%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.44%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.49%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.04%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.73%	90.08%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.53%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.51%	99.23%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.11%	82.50%
CHEMBL299	P17252	Protein kinase C alpha	80.07%	98.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.06%	99.17%

Plants that contains it

• Ixeridium dentatum subsp. dentatum
• Ixeris repens
• Ixeris stolonifera

Cross-Links

• PubChem: 162990147
• LOTUS: LTS0263164
• wikiData: Q105030404