[(3aS,4S,5S,5aR,6S,7S,9aS,9bS)-6,7-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-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: 99f2e379-d198-48c8-9b3c-2b3748a4d078
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4S,5S,5aR,6S,7S,9aS,9bS)-6,7-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-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): CC=C(C)C(=O)OC1C(C2C(C3C1(C(C(C=C3C)O)O)C)OC(=O)C2=C)OC(=O)C4(C(O4)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H]([C@@H]2[C@H]([C@@H]3[C@@]1([C@@H]([C@H](C=C3C)O)O)C)OC(=O)C2=C)OC(=O)[C@@]4([C@@H](O4)C)C
• InChI: InChI=1S/C25H32O9/c1-8-10(2)21(28)33-20-18(32-23(30)25(7)13(5)34-25)15-12(4)22(29)31-17(15)16-11(3)9-14(26)19(27)24(16,20)6/h8-9,13-20,26-27H,4H2,1-3,5-7H3/b10-8-/t13-,14-,15-,16+,17+,18-,19+,20+,24+,25-/m0/s1
• InChI Key: DIWCMNCNQDBDTL-XAWWTZEHSA-N
• Popularity: 1 reference 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): 132.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9528	95.28%
Caco-2	-	0.6724	67.24%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6774	67.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7969	79.69%
OATP1B3 inhibitior	+	0.8949	89.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5088	50.88%
P-glycoprotein inhibitior	+	0.6836	68.36%
P-glycoprotein substrate	-	0.5243	52.43%
CYP3A4 substrate	+	0.6654	66.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.6261	62.61%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.8056	80.56%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.8692	86.92%
CYP2C8 inhibition	-	0.5618	56.18%
CYP inhibitory promiscuity	-	0.7240	72.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.4761	47.61%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.8898	88.98%
Skin irritation	-	0.6396	63.96%
Skin corrosion	-	0.9208	92.08%
Ames mutagenesis	-	0.6232	62.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.5710	57.10%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.8033	80.33%
skin sensitisation	-	0.6823	68.23%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6903	69.03%
Acute Oral Toxicity (c)	III	0.4184	41.84%
Estrogen receptor binding	+	0.7573	75.73%
Androgen receptor binding	+	0.6620	66.20%
Thyroid receptor binding	+	0.5998	59.98%
Glucocorticoid receptor binding	+	0.6080	60.80%
Aromatase binding	+	0.5412	54.12%
PPAR gamma	+	0.6624	66.24%
Honey bee toxicity	-	0.5823	58.23%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9829	98.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.48%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	92.38%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.15%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.22%	95.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.05%	81.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.27%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	85.02%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.57%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.31%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.95%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.58%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.72%	97.25%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162976897
• LOTUS: LTS0029542
• wikiData: Q104981722