(8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-8-yl) 2-methylbut-2-enoate

Details

• Internal ID: fa255677-a3e1-4659-a3e9-e8aca3cff98e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-8-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC(C2(C1(C=C3C(=C(C(=O)O3)C)C2)O)C)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CCC(C2(C1(C=C3C(=C(C(=O)O3)C)C2)O)C)C
• InChI: InChI=1S/C20H26O5/c1-6-11(2)17(21)25-16-8-7-12(3)19(5)9-14-13(4)18(22)24-15(14)10-20(16,19)23/h6,10,12,16,23H,7-9H2,1-5H3
• InChI Key: QWXAMRVOOBEIIT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9899	98.99%
Caco-2	+	0.7606	76.06%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8032	80.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8872	88.72%
OATP1B3 inhibitior	-	0.3054	30.54%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5374	53.74%
BSEP inhibitior	-	0.5364	53.64%
P-glycoprotein inhibitior	-	0.5542	55.42%
P-glycoprotein substrate	-	0.7136	71.36%
CYP3A4 substrate	+	0.6470	64.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8936	89.36%
CYP3A4 inhibition	-	0.6866	68.66%
CYP2C9 inhibition	-	0.7964	79.64%
CYP2C19 inhibition	-	0.7963	79.63%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	+	0.6802	68.02%
CYP2C8 inhibition	-	0.6590	65.90%
CYP inhibitory promiscuity	-	0.9041	90.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5102	51.02%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8806	88.06%
Skin irritation	+	0.6483	64.83%
Skin corrosion	-	0.9072	90.72%
Ames mutagenesis	-	0.6924	69.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7160	71.60%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5129	51.29%
skin sensitisation	-	0.8739	87.39%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4799	47.99%
Acute Oral Toxicity (c)	IV	0.4641	46.41%
Estrogen receptor binding	+	0.7042	70.42%
Androgen receptor binding	+	0.5638	56.38%
Thyroid receptor binding	+	0.6695	66.95%
Glucocorticoid receptor binding	+	0.7014	70.14%
Aromatase binding	-	0.5372	53.72%
PPAR gamma	+	0.6788	67.88%
Honey bee toxicity	-	0.8247	82.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	97.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.92%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.76%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.10%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.10%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.76%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.90%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.58%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.17%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.44%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.49%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.43%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.09%	97.14%

Plants that contains it

• Roldana lobata

Cross-Links

• PubChem: 74327348
• LOTUS: LTS0010664
• wikiData: Q105229448