[(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] (2R)-2-acetyloxy-2-methylbutanoate

Details

• Internal ID: c6a5886b-3f81-44ca-9768-18ae84901027
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] (2R)-2-acetyloxy-2-methylbutanoate
• SMILES (Canonical): CCC(C)(C(=O)OC1C(CC2C(C(CC(C2(C13CO3)COC(=O)C)OC(=O)C)C)(C)C4CC5C=COC5O4)O)OC(=O)C
• SMILES (Isomeric): CC[C@](C)(C(=O)O[C@H]1[C@@H](C[C@@H]2[C@@]([C@@H](C[C@@H]([C@]2([C@@]13CO3)COC(=O)C)OC(=O)C)C)(C)[C@@H]4C[C@H]5C=CO[C@H]5O4)O)OC(=O)C
• InChI: InChI=1S/C31H44O12/c1-8-28(6,43-19(5)34)27(36)42-25-21(35)13-22-29(7,23-12-20-9-10-37-26(20)41-23)16(2)11-24(40-18(4)33)30(22,14-38-17(3)32)31(25)15-39-31/h9-10,16,20-26,35H,8,11-15H2,1-7H3/t16-,20-,21-,22-,23+,24+,25+,26+,28-,29+,30+,31-/m1/s1
• InChI Key: QJRGPOZOQFQNIW-NFIVMRKVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₂
• Molecular Weight: 608.70 g/mol
• Exact Mass: 608.28327683 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	-	0.8008	80.08%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6991	69.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.8863	88.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9873	98.73%
P-glycoprotein inhibitior	+	0.7941	79.41%
P-glycoprotein substrate	+	0.6806	68.06%
CYP3A4 substrate	+	0.7123	71.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	+	0.5254	52.54%
CYP2C9 inhibition	-	0.7881	78.81%
CYP2C19 inhibition	-	0.7968	79.68%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9200	92.00%
CYP2C8 inhibition	+	0.7467	74.67%
CYP inhibitory promiscuity	-	0.8247	82.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4986	49.86%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.5890	58.90%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4352	43.52%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8624	86.24%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5722	57.22%
Acute Oral Toxicity (c)	I	0.5975	59.75%
Estrogen receptor binding	+	0.7756	77.56%
Androgen receptor binding	+	0.7183	71.83%
Thyroid receptor binding	-	0.5052	50.52%
Glucocorticoid receptor binding	+	0.7727	77.27%
Aromatase binding	+	0.7494	74.94%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.7067	70.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9913	99.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.05%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.24%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.47%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	93.48%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.35%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	92.93%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.00%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.16%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.59%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.23%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.73%	94.33%
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	85.24%	93.85%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.10%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.66%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.25%	92.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.23%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.09%	89.34%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.28%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	82.13%	92.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.27%	96.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.25%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.91%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.67%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.12%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.11%	89.00%
CHEMBL5028	O14672	ADAM10	80.07%	97.50%

Plants that contains it

• Clerodendrum trichotomum
• Volkameria inermis

Cross-Links

• PubChem: 76334069
• LOTUS: LTS0132537
• wikiData: Q104397916