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

Details

• Internal ID: 00c16122-b41d-4978-b23e-7c66b9e7e8af
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [4a-(acetyloxymethyl)-5-hydroxy-8-[2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3O)C)(C)CC(C4=CC(=O)OC4)O)COC(=O)C
• SMILES (Isomeric): CCC(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3O)C)(C)CC(C4=CC(=O)OC4)O)COC(=O)C
• InChI: InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(13-35-26)27(14-34-17(4)28)21(30)9-16(3)25(5,23(20)27)11-19(29)18-10-22(31)33-12-18/h10,15-16,19-21,23,29-30H,6-9,11-14H2,1-5H3
• InChI Key: CLJVKWUXMLHMNP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₉
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.26723285 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.6670	66.70%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8651	86.51%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9484	94.84%
P-glycoprotein inhibitior	+	0.6429	64.29%
P-glycoprotein substrate	+	0.6751	67.51%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8932	89.32%
CYP3A4 inhibition	+	0.5730	57.30%
CYP2C9 inhibition	-	0.7615	76.15%
CYP2C19 inhibition	-	0.8586	85.86%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.8700	87.00%
CYP2C8 inhibition	+	0.5506	55.06%
CYP inhibitory promiscuity	-	0.8281	82.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4430	44.30%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9451	94.51%
Skin irritation	+	0.5146	51.46%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4263	42.63%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5149	51.49%
skin sensitisation	-	0.8976	89.76%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7209	72.09%
Acute Oral Toxicity (c)	I	0.3968	39.68%
Estrogen receptor binding	+	0.8753	87.53%
Androgen receptor binding	+	0.7569	75.69%
Thyroid receptor binding	-	0.5336	53.36%
Glucocorticoid receptor binding	+	0.7977	79.77%
Aromatase binding	+	0.7769	77.69%
PPAR gamma	+	0.6011	60.11%
Honey bee toxicity	-	0.7023	70.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9933	99.33%

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	98.88%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.68%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.78%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.75%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.03%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	92.55%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.35%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.32%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.56%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.95%	97.28%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.23%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.91%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.42%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.31%	89.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.96%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.04%	99.23%
CHEMBL5028	O14672	ADAM10	81.98%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.95%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.74%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.57%	95.89%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.48%	94.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.41%	94.80%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.20%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.77%	96.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.43%	95.71%

Plants that contains it

• Ajuga nipponensis

Cross-Links

• PubChem: 14314157
• LOTUS: LTS0222577
• wikiData: Q104963519