[(4S,4aR,5S)-3,4a,5-trimethyl-2,7-dioxo-5,6-dihydro-4H-benzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 7328b56d-276e-4e3b-9164-70c178f593f7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aR,5S)-3,4a,5-trimethyl-2,7-dioxo-5,6-dihydro-4H-benzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)OC2=CC3=CC(=O)CC(C13C)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(C(=O)OC2=CC3=CC(=O)C[C@@H]([C@@]13C)C)C
• InChI: InChI=1S/C20H22O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-15(16)9-13-8-14(21)7-11(3)20(13,17)5/h6,8-9,11,17H,7H2,1-5H3/b10-6-/t11-,17+,20+/m0/s1
• InChI Key: MLPADAGLUVTHDI-CLPURSTRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8572	85.72%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6161	61.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8049	80.49%
OATP1B3 inhibitior	+	0.9042	90.42%
MATE1 inhibitior	-	0.5800	58.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6808	68.08%
P-glycoprotein inhibitior	-	0.4421	44.21%
P-glycoprotein substrate	-	0.7397	73.97%
CYP3A4 substrate	+	0.6364	63.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9043	90.43%
CYP3A4 inhibition	-	0.6760	67.60%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.8995	89.95%
CYP2D6 inhibition	-	0.9586	95.86%
CYP1A2 inhibition	-	0.6370	63.70%
CYP2C8 inhibition	-	0.7001	70.01%
CYP inhibitory promiscuity	-	0.6290	62.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.3980	39.80%
Eye corrosion	-	0.9760	97.60%
Eye irritation	-	0.8185	81.85%
Skin irritation	-	0.5619	56.19%
Skin corrosion	-	0.9050	90.50%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8215	82.15%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.8230	82.30%
skin sensitisation	-	0.6655	66.55%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7050	70.50%
Acute Oral Toxicity (c)	III	0.5757	57.57%
Estrogen receptor binding	+	0.7204	72.04%
Androgen receptor binding	+	0.7214	72.14%
Thyroid receptor binding	-	0.5679	56.79%
Glucocorticoid receptor binding	+	0.6647	66.47%
Aromatase binding	-	0.5940	59.40%
PPAR gamma	+	0.7222	72.22%
Honey bee toxicity	-	0.7569	75.69%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9902	99.02%

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	98.62%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.94%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.90%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.40%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.28%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.32%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.33%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.18%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.33%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.97%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.43%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.09%	100.00%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 102184031
• LOTUS: LTS0153856
• wikiData: Q105166925