[(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] 2-methylpropanoate

Details

• Internal ID: 124f9828-2b0f-4dde-98ca-c57539f82eae
• 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] 2-methylpropanoate
• SMILES (Canonical): CC1CC(C2(C(C1(C)CC(C3=CC(=O)OC3)OC(=O)C(C)C)C(CCC24CO4)OC(=O)C(C)C)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)C[C@@H](C3=CC(=O)OC3)OC(=O)C(C)C)[C@@H](CC[C@]24CO4)OC(=O)C(C)C)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C32H46O11/c1-17(2)28(36)42-23-9-10-31(15-40-31)32(16-39-20(6)33)25(41-21(7)34)11-19(5)30(8,27(23)32)13-24(43-29(37)18(3)4)22-12-26(35)38-14-22/h12,17-19,23-25,27H,9-11,13-16H2,1-8H3/t19-,23-,24+,25+,27-,30+,31+,32-/m1/s1
• InChI Key: ANLWCQMYWXHLJK-LXEOJQGKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₆O₁₁
• Molecular Weight: 606.70 g/mol
• Exact Mass: 606.30401228 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 11
• 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	+	0.9856	98.56%
Caco-2	-	0.7700	77.00%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8217	82.17%
OATP2B1 inhibitior	-	0.7234	72.34%
OATP1B1 inhibitior	+	0.8661	86.61%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.9726	97.26%
P-glycoprotein inhibitior	+	0.8523	85.23%
P-glycoprotein substrate	+	0.6578	65.78%
CYP3A4 substrate	+	0.6905	69.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8993	89.93%
CYP3A4 inhibition	-	0.8314	83.14%
CYP2C9 inhibition	-	0.7097	70.97%
CYP2C19 inhibition	-	0.7520	75.20%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.7918	79.18%
CYP2C8 inhibition	+	0.5513	55.13%
CYP inhibitory promiscuity	-	0.7974	79.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5061	50.61%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8940	89.40%
Skin irritation	-	0.6497	64.97%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7071	70.71%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7657	76.57%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6344	63.44%
Acute Oral Toxicity (c)	III	0.4248	42.48%
Estrogen receptor binding	+	0.8471	84.71%
Androgen receptor binding	+	0.7451	74.51%
Thyroid receptor binding	+	0.5555	55.55%
Glucocorticoid receptor binding	+	0.7782	77.82%
Aromatase binding	+	0.7210	72.10%
PPAR gamma	+	0.7455	74.55%
Honey bee toxicity	-	0.7010	70.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9956	99.56%

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%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.53%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.43%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.06%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.84%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.36%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.46%	94.80%
CHEMBL221	P23219	Cyclooxygenase-1	91.36%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.52%	92.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.32%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.79%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.09%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.02%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.39%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.76%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.17%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.09%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.55%	89.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.87%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.46%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.20%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.01%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.96%	92.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.89%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	80.36%	91.19%

Plants that contains it

• Ajuga macrosperma

Cross-Links

• PubChem: 163078154
• LOTUS: LTS0099616
• wikiData: Q104915268