[(4S,4aR,5R,6S)-6-acetyloxy-3,4a,5-trimethyl-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-4-yl] propanoate

Details

• Internal ID: 22a0f35b-39e0-43f5-9de1-a31ecd6d8f83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aR,5R,6S)-6-acetyloxy-3,4a,5-trimethyl-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-4-yl] propanoate
• SMILES (Canonical): CCC(=O)OC1C2=C(CC3=CCC(C(C13C)C)OC(=O)C)OC=C2C
• SMILES (Isomeric): CCC(=O)O[C@@H]1C2=C(CC3=CC[C@@H]([C@@H]([C@@]13C)C)OC(=O)C)OC=C2C
• InChI: InChI=1S/C20H26O5/c1-6-17(22)25-19-18-11(2)10-23-16(18)9-14-7-8-15(24-13(4)21)12(3)20(14,19)5/h7,10,12,15,19H,6,8-9H2,1-5H3/t12-,15-,19+,20+/m0/s1
• InChI Key: JBUJFKRPTLTIIY-KKFOWGLESA-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): 65.70 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8377	83.77%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7016	70.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8687	86.87%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7389	73.89%
P-glycoprotein inhibitior	+	0.5915	59.15%
P-glycoprotein substrate	-	0.6600	66.00%
CYP3A4 substrate	+	0.6484	64.84%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	-	0.8292	82.92%
CYP3A4 inhibition	+	0.5797	57.97%
CYP2C9 inhibition	-	0.6038	60.38%
CYP2C19 inhibition	-	0.5105	51.05%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	+	0.5134	51.34%
CYP2C8 inhibition	+	0.5792	57.92%
CYP inhibitory promiscuity	+	0.7929	79.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4928	49.28%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9669	96.69%
Skin irritation	-	0.6701	67.01%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7978	79.78%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6998	69.98%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7671	76.71%
Acute Oral Toxicity (c)	III	0.5988	59.88%
Estrogen receptor binding	+	0.6351	63.51%
Androgen receptor binding	+	0.5892	58.92%
Thyroid receptor binding	-	0.5173	51.73%
Glucocorticoid receptor binding	+	0.7783	77.83%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6871	68.71%
Honey bee toxicity	-	0.8278	82.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.55%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	89.45%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.94%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.69%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.51%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.15%	96.95%
CHEMBL5255	O00206	Toll-like receptor 4	82.27%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	82.10%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.99%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.89%	97.21%

Plants that contains it

• Senecio subumbellatus

Cross-Links

• PubChem: 15694267
• LOTUS: LTS0091302
• wikiData: Q105124586