[8-acetyloxy-8a-(acetyloxymethyl)-5-(5-ethoxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylbutanoate

Details

• Internal ID: e4ef4dfc-f2c4-486c-a191-33dc9de0004f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [8-acetyloxy-8a-(acetyloxymethyl)-5-(5-ethoxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(CC2C(C(CC(C2(C13CO3)COC(=O)C)OC(=O)C)C)(C)C4CC5CC(OC5O4)OCC)O
• SMILES (Isomeric): CCC(C)C(=O)OC1C(CC2C(C(CC(C2(C13CO3)COC(=O)C)OC(=O)C)C)(C)C4CC5CC(OC5O4)OCC)O
• InChI: InChI=1S/C31H48O11/c1-8-16(3)27(35)42-26-21(34)13-22-29(7,23-11-20-12-25(36-9-2)41-28(20)40-23)17(4)10-24(39-19(6)33)30(22,14-37-18(5)32)31(26)15-38-31/h16-17,20-26,28,34H,8-15H2,1-7H3
• InChI Key: BYEWAYHTOJPYKI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₈O₁₁
• Molecular Weight: 596.70 g/mol
• Exact Mass: 596.31966234 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.7878	78.78%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6911	69.11%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.8450	84.50%
OATP1B3 inhibitior	+	0.8905	89.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8419	84.19%
P-glycoprotein inhibitior	+	0.7272	72.72%
P-glycoprotein substrate	+	0.6506	65.06%
CYP3A4 substrate	+	0.6980	69.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	+	0.5785	57.85%
CYP2C9 inhibition	-	0.7430	74.30%
CYP2C19 inhibition	-	0.7601	76.01%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.9187	91.87%
CYP2C8 inhibition	+	0.5628	56.28%
CYP inhibitory promiscuity	-	0.8641	86.41%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5301	53.01%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.6521	65.21%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5934	59.34%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5608	56.08%
skin sensitisation	-	0.8804	88.04%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7995	79.95%
Acute Oral Toxicity (c)	I	0.5140	51.40%
Estrogen receptor binding	+	0.7581	75.81%
Androgen receptor binding	+	0.7080	70.80%
Thyroid receptor binding	-	0.6063	60.63%
Glucocorticoid receptor binding	+	0.6867	68.67%
Aromatase binding	+	0.6898	68.98%
PPAR gamma	+	0.6582	65.82%
Honey bee toxicity	-	0.7096	70.96%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9806	98.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.04%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.56%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.53%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.62%	85.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.30%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.94%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.12%	97.21%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.98%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	91.61%	91.19%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.11%	89.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.82%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	90.40%	89.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.63%	96.47%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.04%	82.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.03%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	87.98%	97.79%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.71%	96.77%
CHEMBL299	P17252	Protein kinase C alpha	87.40%	98.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.17%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.76%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	85.25%	92.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.30%	96.61%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.13%	92.62%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.91%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.67%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.46%	91.24%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.33%	92.86%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.12%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.73%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.68%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.29%	89.00%

Plants that contains it

• Ajuga chamaepitys
• Ajuga parviflora

Cross-Links

• PubChem: 13966154
• LOTUS: LTS0255690
• wikiData: Q104949181