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

Details

• Internal ID: 23833ffc-bd66-4b47-820c-3429f1d1ad59
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: [(4R,4aR,5S,7R,8S,8aR)-8-[(2S,3aS,5R,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-5-acetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl 2-methylpropanoate
• SMILES (Canonical): CC1CC(C2(C(C1(C)C3CC4CC(OC4O3)O)CCCC25CO5)COC(=O)C(C)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)[C@@H]3C[C@H]4C[C@@H](O[C@H]4O3)O)CCC[C@]25CO5)COC(=O)C(C)C)OC(=O)C
• InChI: InChI=1S/C26H40O8/c1-14(2)22(29)30-13-26-18(7-6-8-25(26)12-31-25)24(5,15(3)9-20(26)32-16(4)27)19-10-17-11-21(28)34-23(17)33-19/h14-15,17-21,23,28H,6-13H2,1-5H3/t15-,17+,18-,19+,20+,21-,23-,24+,25+,26+/m1/s1
• InChI Key: LRLXFVKMSHWWOB-DDSDSLNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₈
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.27231823 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9660	96.60%
Caco-2	-	0.6877	68.77%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8235	82.35%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8731	87.31%
OATP1B3 inhibitior	+	0.8973	89.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5884	58.84%
P-glycoprotein inhibitior	-	0.4528	45.28%
P-glycoprotein substrate	-	0.5718	57.18%
CYP3A4 substrate	+	0.6918	69.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.6798	67.98%
CYP2C9 inhibition	-	0.6747	67.47%
CYP2C19 inhibition	-	0.7722	77.22%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9290	92.90%
CYP2C8 inhibition	+	0.5377	53.77%
CYP inhibitory promiscuity	-	0.9242	92.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5488	54.88%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.6867	68.67%
Skin corrosion	-	0.9288	92.88%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5620	56.20%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.6024	60.24%
skin sensitisation	-	0.8836	88.36%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4834	48.34%
Acute Oral Toxicity (c)	I	0.5301	53.01%
Estrogen receptor binding	+	0.8807	88.07%
Androgen receptor binding	+	0.6797	67.97%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.7111	71.11%
Aromatase binding	+	0.7218	72.18%
PPAR gamma	+	0.7435	74.35%
Honey bee toxicity	-	0.7152	71.52%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9781	97.81%

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	98.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.83%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	94.60%	89.05%
CHEMBL2581	P07339	Cathepsin D	94.14%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.19%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.79%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.12%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	89.89%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.60%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.01%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.83%	82.69%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.09%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.40%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.31%	91.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.18%	89.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.38%	93.04%
CHEMBL2996	Q05655	Protein kinase C delta	84.80%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	84.52%	92.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.33%	97.28%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.05%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.87%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.35%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.33%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.04%	95.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.82%	85.31%
CHEMBL5028	O14672	ADAM10	82.68%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.30%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.80%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.49%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.28%	95.71%
CHEMBL221	P23219	Cyclooxygenase-1	80.94%	90.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.90%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.55%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.22%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.00%	98.75%

Plants that contains it

• Scutellaria alpina
• Scutellaria caucasica

Cross-Links

• PubChem: 21606600
• LOTUS: LTS0036508
• wikiData: Q105156206