[(3aS,4S,5S,5aR,6R,9aS,9bS)-5-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 0b9c1b85-ebd2-43cb-b2da-004d724c901a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4S,5S,5aR,6R,9aS,9bS)-5-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2C3C(C4C(=CCC(C4(C2OC(=O)C5(C(O5)C)C)C)O)C)OC(=O)C3=C
• SMILES (Isomeric): C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2[C@@H]3[C@H]([C@H]4C(=CC[C@H]([C@@]4([C@@H]2OC(=O)[C@@]5([C@@H](O5)C)C)C)O)C)OC(=O)C3=C
• InChI: InChI=1S/C25H32O9/c1-10-8-9-14(26)23(5)16(10)17-15(11(2)20(27)30-17)18(31-21(28)24(6)12(3)33-24)19(23)32-22(29)25(7)13(4)34-25/h8,12-19,26H,2,9H2,1,3-7H3/t12-,13-,14+,15-,16+,17+,18-,19+,23-,24-,25-/m0/s1
• InChI Key: GUUNMCCZCVIQOO-OECVMYFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₉
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.20463259 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.6330	63.30%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6267	62.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8677	86.77%
OATP1B3 inhibitior	+	0.8861	88.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5448	54.48%
P-glycoprotein inhibitior	+	0.7041	70.41%
P-glycoprotein substrate	-	0.6117	61.17%
CYP3A4 substrate	+	0.6483	64.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	+	0.5520	55.20%
CYP2C9 inhibition	-	0.9379	93.79%
CYP2C19 inhibition	-	0.8940	89.40%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	-	0.6627	66.27%
CYP inhibitory promiscuity	-	0.8841	88.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4174	41.74%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.5894	58.94%
Skin corrosion	-	0.8942	89.42%
Ames mutagenesis	-	0.5918	59.18%
Human Ether-a-go-go-Related Gene inhibition	-	0.5958	59.58%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.7117	71.17%
skin sensitisation	-	0.6493	64.93%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6921	69.21%
Acute Oral Toxicity (c)	III	0.4128	41.28%
Estrogen receptor binding	+	0.7500	75.00%
Androgen receptor binding	+	0.7047	70.47%
Thyroid receptor binding	+	0.6250	62.50%
Glucocorticoid receptor binding	+	0.6616	66.16%
Aromatase binding	+	0.6583	65.83%
PPAR gamma	+	0.6509	65.09%
Honey bee toxicity	-	0.6947	69.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9655	96.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.00%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.02%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	94.44%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.50%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.05%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.14%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.08%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.02%	93.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.75%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.90%	93.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.98%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.74%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.70%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.85%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.37%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.48%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.23%	96.09%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162902855
• LOTUS: LTS0092419
• wikiData: Q105020564