[(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-7,8-dimethyl-8-[(2S)-2-(2-methylpropanoyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 63096bfb-0375-4be3-91f8-6020a1871a1f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-7,8-dimethyl-8-[(2S)-2-(2-methylpropanoyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)CC(C4=CC(=O)OC4)OC(=O)C(C)C)COC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1CC[C@]2(CO2)[C@]3([C@H]1[C@@]([C@@H](C[C@@H]3OC(=O)C)C)(C)C[C@@H](C4=CC(=O)OC4)OC(=O)C(C)C)COC(=O)C
• InChI: InChI=1S/C33H48O11/c1-9-19(4)30(38)43-24-10-11-32(16-41-32)33(17-40-21(6)34)26(42-22(7)35)12-20(5)31(8,28(24)33)14-25(44-29(37)18(2)3)23-13-27(36)39-15-23/h13,18-20,24-26,28H,9-12,14-17H2,1-8H3/t19-,20-,24-,25+,26+,28-,31+,32+,33-/m1/s1
• InChI Key: CUISVSYCDKXXAJ-YXQYNZQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₈O₁₁
• Molecular Weight: 620.70 g/mol
• Exact Mass: 620.31966234 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	-	0.7674	76.74%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7815	78.15%
OATP2B1 inhibitior	-	0.7241	72.41%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9863	98.63%
P-glycoprotein inhibitior	+	0.8644	86.44%
P-glycoprotein substrate	+	0.6797	67.97%
CYP3A4 substrate	+	0.6980	69.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8993	89.93%
CYP3A4 inhibition	-	0.7434	74.34%
CYP2C9 inhibition	-	0.6909	69.09%
CYP2C19 inhibition	-	0.6825	68.25%
CYP2D6 inhibition	-	0.9081	90.81%
CYP1A2 inhibition	-	0.8053	80.53%
CYP2C8 inhibition	+	0.6031	60.31%
CYP inhibitory promiscuity	-	0.7019	70.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5003	50.03%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.6451	64.51%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7080	70.80%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7928	79.28%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5733	57.33%
Acute Oral Toxicity (c)	III	0.5316	53.16%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.7488	74.88%
Thyroid receptor binding	+	0.5369	53.69%
Glucocorticoid receptor binding	+	0.7800	78.00%
Aromatase binding	+	0.7237	72.37%
PPAR gamma	+	0.7140	71.40%
Honey bee toxicity	-	0.7048	70.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	98.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.22%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.67%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.66%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.97%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.32%	82.69%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.30%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.39%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.63%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	89.40%	90.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.32%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.92%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.39%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.90%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.81%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.28%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.28%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.04%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	82.35%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.08%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.28%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.01%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.23%	96.47%

Plants that contains it

• Ajuga macrosperma

Cross-Links

• PubChem: 163029586
• LOTUS: LTS0153102
• wikiData: Q104970294