[(1R,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-4a-(acetyloxymethyl)-3-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 1e8a1055-c40e-470a-a953-bccae52dee8d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-4a-(acetyloxymethyl)-3-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)C4CC5CCOC5O4)COC(=O)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@@H]([C@]2(CO2)[C@]3([C@H]1[C@@]([C@@H](C[C@@H]3OC(=O)C)C)(C)[C@@H]4C[C@H]5CCO[C@H]5O4)COC(=O)C)O
• InChI: InChI=1S/C29H42O10/c1-7-15(2)25(33)38-20-12-21(32)29(14-36-29)28(13-35-17(4)30)23(37-18(5)31)10-16(3)27(6,24(20)28)22-11-19-8-9-34-26(19)39-22/h7,16,19-24,26,32H,8-14H2,1-6H3/b15-7+/t16-,19-,20-,21+,22+,23+,24-,26+,27-,28-,29-/m1/s1
• InChI Key: QSLIYGYTUHOQHM-JHNLQVKESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₀
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.27779753 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9812	98.12%
Caco-2	-	0.7479	74.79%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8419	84.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8533	85.33%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9569	95.69%
P-glycoprotein inhibitior	+	0.7527	75.27%
P-glycoprotein substrate	+	0.6126	61.26%
CYP3A4 substrate	+	0.7082	70.82%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8926	89.26%
CYP3A4 inhibition	-	0.6712	67.12%
CYP2C9 inhibition	-	0.7202	72.02%
CYP2C19 inhibition	-	0.8413	84.13%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.8989	89.89%
CYP2C8 inhibition	+	0.5984	59.84%
CYP inhibitory promiscuity	-	0.8974	89.74%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4732	47.32%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9234	92.34%
Skin irritation	-	0.5211	52.11%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4548	45.48%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8166	81.66%
Acute Oral Toxicity (c)	I	0.7354	73.54%
Estrogen receptor binding	+	0.8830	88.30%
Androgen receptor binding	+	0.6894	68.94%
Thyroid receptor binding	-	0.4885	48.85%
Glucocorticoid receptor binding	+	0.7751	77.51%
Aromatase binding	+	0.7501	75.01%
PPAR gamma	+	0.7615	76.15%
Honey bee toxicity	-	0.6882	68.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9888	98.88%

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	97.32%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.44%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.72%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.68%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.56%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	89.50%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.42%	91.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.07%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.82%	92.94%
CHEMBL2581	P07339	Cathepsin D	87.61%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	87.05%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.78%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.56%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.11%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.90%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.26%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.20%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.13%	97.21%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.86%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.81%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.09%	97.25%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.93%	98.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.86%	94.80%

Plants that contains it

• Ajuga orientalis
• Ajuga reptans

Cross-Links

• PubChem: 101701110
• LOTUS: LTS0191385
• wikiData: Q105227095