[(3aS,4R,5aS,6R,9aR,9bS)-6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 779afe03-acbb-4938-8791-2d9c4d69fde9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4R,5aS,6R,9aR,9bS)-6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CC3(C(CCC(=C)C3(C4C2C(=C)C(=O)O4)O)O)C
• SMILES (Isomeric): C[C@H]1[C@@](O1)(C)C(=O)O[C@@H]2C[C@]3([C@@H](CCC(=C)[C@@]3([C@@H]4[C@H]2C(=C)C(=O)O4)O)O)C
• InChI: InChI=1S/C20H26O7/c1-9-6-7-13(21)18(4)8-12(25-17(23)19(5)11(3)27-19)14-10(2)16(22)26-15(14)20(9,18)24/h11-15,21,24H,1-2,6-8H2,3-5H3/t11-,12+,13+,14-,15-,18-,19-,20-/m0/s1
• InChI Key: IXJLFSPGJWNXAL-DJDLVFCISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9580	95.80%
Caco-2	-	0.5808	58.08%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.8831	88.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6374	63.74%
BSEP inhibitior	-	0.9269	92.69%
P-glycoprotein inhibitior	-	0.7152	71.52%
P-glycoprotein substrate	-	0.6615	66.15%
CYP3A4 substrate	+	0.6736	67.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	+	0.5266	52.66%
CYP2C9 inhibition	-	0.7867	78.67%
CYP2C19 inhibition	-	0.8519	85.19%
CYP2D6 inhibition	-	0.9377	93.77%
CYP1A2 inhibition	-	0.7682	76.82%
CYP2C8 inhibition	-	0.7103	71.03%
CYP inhibitory promiscuity	-	0.9074	90.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4936	49.36%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9355	93.55%
Skin irritation	+	0.5401	54.01%
Skin corrosion	-	0.9045	90.45%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5437	54.37%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.8385	83.85%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4566	45.66%
Acute Oral Toxicity (c)	I	0.3956	39.56%
Estrogen receptor binding	+	0.8180	81.80%
Androgen receptor binding	+	0.6827	68.27%
Thyroid receptor binding	+	0.6332	63.32%
Glucocorticoid receptor binding	+	0.8014	80.14%
Aromatase binding	+	0.6689	66.89%
PPAR gamma	+	0.5622	56.22%
Honey bee toxicity	-	0.8147	81.47%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9938	99.38%

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	96.56%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.89%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	93.13%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.33%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.55%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.57%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.40%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.71%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.59%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.28%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.51%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.09%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.88%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.77%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.07%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.12%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.91%	94.00%
CHEMBL2581	P07339	Cathepsin D	80.32%	98.95%
CHEMBL4588	P22894	Matrix metalloproteinase 8	80.25%	94.66%

Plants that contains it

• Tithonia pedunculata

Cross-Links

• PubChem: 163043720
• LOTUS: LTS0045723
• wikiData: Q105122216