[(1R,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aR)-3a,4,5,6a-tetrahydrofuro[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: 03772a9a-5575-4b44-9d3f-94966e065a2b
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aR)-3a,4,5,6a-tetrahydrofuro[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)C4CC5C=COC5O4)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]5C=CO[C@@H]5O4)COC(=O)C)O
• InChI: InChI=1S/C29H40O10/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/h7-9,16,19-24,26,32H,10-14H2,1-6H3/b15-7+/t16-,19-,20-,21+,22+,23+,24-,26-,27-,28-,29-/m1/s1
• InChI Key: VHMXRHYBQSWLTN-MDHVGLNGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₁₀
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.26214747 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.82
• 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	+	0.9831	98.31%
Caco-2	-	0.7664	76.64%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7997	79.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8393	83.93%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9709	97.09%
P-glycoprotein inhibitior	+	0.7530	75.30%
P-glycoprotein substrate	+	0.6295	62.95%
CYP3A4 substrate	+	0.7037	70.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8924	89.24%
CYP3A4 inhibition	-	0.6109	61.09%
CYP2C9 inhibition	-	0.7560	75.60%
CYP2C19 inhibition	-	0.8229	82.29%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.9092	90.92%
CYP2C8 inhibition	+	0.6026	60.26%
CYP inhibitory promiscuity	-	0.8657	86.57%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5037	50.37%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.5881	58.81%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6950	69.50%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8641	86.41%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.8210	82.10%
Acute Oral Toxicity (c)	I	0.7610	76.10%
Estrogen receptor binding	+	0.8845	88.45%
Androgen receptor binding	+	0.6945	69.45%
Thyroid receptor binding	+	0.5698	56.98%
Glucocorticoid receptor binding	+	0.7607	76.07%
Aromatase binding	+	0.7189	71.89%
PPAR gamma	+	0.7363	73.63%
Honey bee toxicity	-	0.6559	65.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9923	99.23%

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	97.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.25%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.80%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.46%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	90.00%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.66%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	89.21%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.34%	97.21%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.65%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.13%	91.07%
CHEMBL2581	P07339	Cathepsin D	85.61%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.14%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.00%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.64%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.55%	94.33%
CHEMBL5028	O14672	ADAM10	80.02%	97.50%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163032577
• LOTUS: LTS0105298
• wikiData: Q105286510