[(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] (2S)-2-methylbutanoate

Details

• Internal ID: 9fd96993-95e4-4a50-867f-e8a6751d3cbc
• 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] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)C4CC5CCOC5O4)COC(=O)C)O
• SMILES (Isomeric): CC[C@H](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/C29H44O10/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/h15-16,19-24,26,32H,7-14H2,1-6H3/t15-,16+,19+,20+,21-,22-,23-,24+,26-,27+,28+,29+/m0/s1
• InChI Key: YKWBDFBNTYGFFZ-BZQNXUIFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₀
• Molecular Weight: 552.70 g/mol
• Exact Mass: 552.29344760 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	-	0.7015	70.15%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7862	78.62%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8617	86.17%
OATP1B3 inhibitior	+	0.8871	88.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.8879	88.79%
P-glycoprotein inhibitior	+	0.6745	67.45%
P-glycoprotein substrate	+	0.6270	62.70%
CYP3A4 substrate	+	0.6952	69.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	+	0.5692	56.92%
CYP2C9 inhibition	-	0.6720	67.20%
CYP2C19 inhibition	-	0.7330	73.30%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9129	91.29%
CYP2C8 inhibition	+	0.5893	58.93%
CYP inhibitory promiscuity	-	0.8988	89.88%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9040	90.40%
Skin irritation	-	0.6197	61.97%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5211	52.11%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9281	92.81%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5922	59.22%
Acute Oral Toxicity (c)	I	0.4358	43.58%
Estrogen receptor binding	+	0.8472	84.72%
Androgen receptor binding	+	0.7163	71.63%
Thyroid receptor binding	-	0.5240	52.40%
Glucocorticoid receptor binding	+	0.7417	74.17%
Aromatase binding	+	0.7303	73.03%
PPAR gamma	+	0.7154	71.54%
Honey bee toxicity	-	0.7511	75.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9774	97.74%

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	98.71%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.03%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.23%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.16%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.12%	91.11%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	92.88%	98.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	92.16%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.39%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.37%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	89.57%	91.19%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.51%	82.50%
CHEMBL2996	Q05655	Protein kinase C delta	87.23%	97.79%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.88%	97.28%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.57%	97.21%
CHEMBL226	P30542	Adenosine A1 receptor	86.05%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.88%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.71%	96.77%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.29%	95.71%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.99%	97.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.72%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.59%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.17%	92.62%
CHEMBL221	P23219	Cyclooxygenase-1	83.15%	90.17%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.96%	89.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.80%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.32%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.96%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.55%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.98%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.87%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.15%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.12%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	80.12%	92.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.04%	82.69%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 21123465
• LOTUS: LTS0090369
• wikiData: Q105349914