[(Z,2S,3R,5S,8E)-3,5-diacetyloxy-8-(5-oxofuran-2-ylidene)oct-6-en-2-yl] acetate

Details

• Internal ID: c8e6455d-6d58-431a-b306-5f036aa2cf1a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(Z,2S,3R,5S,8E)-3,5-diacetyloxy-8-(5-oxofuran-2-ylidene)oct-6-en-2-yl] acetate
• SMILES (Canonical): CC(C(CC(C=CC=C1C=CC(=O)O1)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]([C@@H](C[C@@H](/C=C\C=C\1/C=CC(=O)O1)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C18H22O8/c1-11(23-12(2)19)17(25-14(4)21)10-16(24-13(3)20)7-5-6-15-8-9-18(22)26-15/h5-9,11,16-17H,10H2,1-4H3/b7-5-,15-6+/t11-,16+,17+/m0/s1
• InChI Key: KDEWTQXXMLNSQJ-KMVPTDSLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₈
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.13146766 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.74
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.5515	55.15%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6683	66.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	+	0.9051	90.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7389	73.89%
P-glycoprotein inhibitior	+	0.6506	65.06%
P-glycoprotein substrate	-	0.8199	81.99%
CYP3A4 substrate	+	0.5340	53.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.8730	87.30%
CYP2C9 inhibition	-	0.9215	92.15%
CYP2C19 inhibition	-	0.7395	73.95%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.7600	76.00%
CYP2C8 inhibition	-	0.8615	86.15%
CYP inhibitory promiscuity	-	0.7437	74.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8628	86.28%
Carcinogenicity (trinary)	Non-required	0.5569	55.69%
Eye corrosion	-	0.8335	83.35%
Eye irritation	-	0.9437	94.37%
Skin irritation	-	0.6773	67.73%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6852	68.52%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6422	64.22%
skin sensitisation	-	0.7124	71.24%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.7013	70.13%
Acute Oral Toxicity (c)	III	0.5087	50.87%
Estrogen receptor binding	+	0.8125	81.25%
Androgen receptor binding	-	0.7198	71.98%
Thyroid receptor binding	-	0.5053	50.53%
Glucocorticoid receptor binding	+	0.6793	67.93%
Aromatase binding	-	0.5764	57.64%
PPAR gamma	-	0.6526	65.26%
Honey bee toxicity	-	0.8588	85.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8151	81.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.67%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.02%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.59%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.57%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.51%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.24%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.65%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.30%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.91%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.40%	96.00%

Plants that contains it

• Mitragyna speciosa

Cross-Links

• PubChem: 134840879
• LOTUS: LTS0267477
• wikiData: Q105312831