[(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R,3S)-2-hydroxy-3-methylpentanoate

Details

• Internal ID: 877fe704-4dcd-46df-aa4e-e3f98bc9a605
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R,3S)-2-hydroxy-3-methylpentanoate
• SMILES (Canonical): CCC(C)C(C(=O)OC1CC(=C)C2CC(=C(C2C3C1C(=C)C(=O)O3)C)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]2CC(=C([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C)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/h10,14,16-24,27-32H,3,5-9H2,1-2,4H3/t10-,14-,16+,17+,18-,19+,20+,21+,22-,23+,24+,27+/m0/s1
• InChI Key: UBVAFNHLMOOUAJ-YEMRPPDESA-N
• Popularity: 2 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: 0.60
• Atomic LogP (AlogP): 0.09
• 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	+	0.8287	82.87%
Caco-2	-	0.8437	84.37%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6719	67.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8328	83.28%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5740	57.40%
P-glycoprotein inhibitior	-	0.5225	52.25%
P-glycoprotein substrate	-	0.5663	56.63%
CYP3A4 substrate	+	0.6687	66.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8886	88.86%
CYP3A4 inhibition	-	0.5422	54.22%
CYP2C9 inhibition	-	0.7878	78.78%
CYP2C19 inhibition	-	0.7813	78.13%
CYP2D6 inhibition	-	0.9313	93.13%
CYP1A2 inhibition	-	0.7860	78.60%
CYP2C8 inhibition	+	0.4619	46.19%
CYP inhibitory promiscuity	-	0.8627	86.27%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6757	67.57%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9108	91.08%
Skin irritation	-	0.6644	66.44%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6428	64.28%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7093	70.93%
skin sensitisation	-	0.8693	86.93%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7470	74.70%
Acute Oral Toxicity (c)	III	0.6040	60.40%
Estrogen receptor binding	+	0.7445	74.45%
Androgen receptor binding	+	0.6221	62.21%
Thyroid receptor binding	-	0.5395	53.95%
Glucocorticoid receptor binding	+	0.5869	58.69%
Aromatase binding	+	0.5689	56.89%
PPAR gamma	+	0.5579	55.79%
Honey bee toxicity	-	0.7164	71.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	98.78%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.65%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.49%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.37%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.13%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.61%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.26%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.26%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.24%	96.37%
CHEMBL2996	Q05655	Protein kinase C delta	86.73%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.69%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.48%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.89%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.79%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.68%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.81%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.45%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.54%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.85%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.83%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.27%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.43%	95.89%

Plants that contains it

• Ixeris japonica
• Ixeris stolonifera

Cross-Links

• PubChem: 163001442
• LOTUS: LTS0012620
• wikiData: Q105269682