[(1S,4aS,6S,7R,7aS)-6-acetyloxy-4-[[(2R)-2-acetyloxy-3-methylbutanoyl]oxymethyl]spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-1-yl] (3S)-3-methylpentanoate

Details

• Internal ID: f20920af-5ef5-49ce-8375-4c2698d32d2c
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(1S,4aS,6S,7R,7aS)-6-acetyloxy-4-[[(2R)-2-acetyloxy-3-methylbutanoyl]oxymethyl]spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-1-yl] (3S)-3-methylpentanoate
• SMILES (Canonical): CCC(C)CC(=O)OC1C2C(CC(C23CO3)OC(=O)C)C(=CO1)COC(=O)C(C(C)C)OC(=O)C
• SMILES (Isomeric): CC[C@H](C)CC(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@]23CO3)OC(=O)C)C(=CO1)COC(=O)[C@@H](C(C)C)OC(=O)C
• InChI: InChI=1S/C25H36O10/c1-7-14(4)8-20(28)35-24-21-18(9-19(33-15(5)26)25(21)12-32-25)17(11-31-24)10-30-23(29)22(13(2)3)34-16(6)27/h11,13-14,18-19,21-22,24H,7-10,12H2,1-6H3/t14-,18+,19-,21+,22+,24-,25+/m0/s1
• InChI Key: GWGCPLJQSZLBJE-JEORNDINSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₁₀
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.23084734 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	-	0.6829	68.29%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7120	71.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8320	83.20%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9038	90.38%
P-glycoprotein inhibitior	+	0.7623	76.23%
P-glycoprotein substrate	+	0.5155	51.55%
CYP3A4 substrate	+	0.6500	65.00%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.8515	85.15%
CYP2C9 inhibition	-	0.7990	79.90%
CYP2C19 inhibition	-	0.7236	72.36%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.8209	82.09%
CYP2C8 inhibition	+	0.5666	56.66%
CYP inhibitory promiscuity	-	0.8426	84.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5867	58.67%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.8897	88.97%
Skin irritation	-	0.7201	72.01%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4894	48.94%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5569	55.69%
skin sensitisation	-	0.6867	68.67%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7102	71.02%
Acute Oral Toxicity (c)	III	0.4959	49.59%
Estrogen receptor binding	+	0.7687	76.87%
Androgen receptor binding	+	0.6868	68.68%
Thyroid receptor binding	-	0.5654	56.54%
Glucocorticoid receptor binding	+	0.7946	79.46%
Aromatase binding	+	0.5800	58.00%
PPAR gamma	+	0.6254	62.54%
Honey bee toxicity	-	0.7853	78.53%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9819	98.19%

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	97.81%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	96.22%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.44%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.09%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.16%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.36%	97.25%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.79%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.86%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.83%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.30%	82.69%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.55%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.89%	82.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.34%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.70%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.46%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	80.37%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.18%	97.14%

Plants that contains it

• Valeriana pulvinata

Cross-Links

• PubChem: 162944625
• LOTUS: LTS0170815
• wikiData: Q105022311