[(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,3S)-2-hydroxy-3-methylpentanoate

Details

• Internal ID: b02e4371-c059-4860-a5e1-ab728da75377
• 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,3S)-2-hydroxy-3-methylpentanoate
• SMILES (Canonical): CCC(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@H](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/C27H38O11/c1-6-10(2)20(29)26(34)35-16-7-11(3)14-8-15(12(4)18(14)24-19(16)13(5)25(33)38-24)36-27-23(32)22(31)21(30)17(9-28)37-27/h10,14-24,27-32H,3-9H2,1-2H3/t10-,14-,15-,16+,17+,18-,19+,20+,21+,22-,23+,24+,27+/m0/s1
• InChI Key: OEZZDIKUWYTZHP-WJDHRHFLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₁
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.24141202 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7464	74.64%
Caco-2	-	0.8565	85.65%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7072	70.72%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8094	80.94%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6658	66.58%
P-glycoprotein inhibitior	-	0.5633	56.33%
P-glycoprotein substrate	-	0.5160	51.60%
CYP3A4 substrate	+	0.6738	67.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8925	89.25%
CYP3A4 inhibition	-	0.7258	72.58%
CYP2C9 inhibition	-	0.8268	82.68%
CYP2C19 inhibition	-	0.7833	78.33%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.8536	85.36%
CYP2C8 inhibition	-	0.5689	56.89%
CYP inhibitory promiscuity	-	0.8398	83.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6815	68.15%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.9117	91.17%
Skin irritation	-	0.7366	73.66%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4031	40.31%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6143	61.43%
skin sensitisation	-	0.8493	84.93%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6468	64.68%
Acute Oral Toxicity (c)	III	0.5401	54.01%
Estrogen receptor binding	+	0.7352	73.52%
Androgen receptor binding	+	0.6350	63.50%
Thyroid receptor binding	-	0.5443	54.43%
Glucocorticoid receptor binding	+	0.5558	55.58%
Aromatase binding	+	0.5877	58.77%
PPAR gamma	+	0.5844	58.44%
Honey bee toxicity	-	0.6540	65.40%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9628	96.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	97.13%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.80%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.67%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.41%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	91.79%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	88.25%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.23%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.55%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.59%	95.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.71%	82.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.81%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.21%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.94%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.78%	99.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.75%	98.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.42%	95.83%

Plants that contains it

• Ixeridium dentatum subsp. dentatum
• Ixeris japonica
• Ixeris stolonifera

Cross-Links

• PubChem: 162981169
• LOTUS: LTS0073476
• wikiData: Q105190732