[(1R,2S,4R,5S,6R,8R,10R,11R)-5-[(2S,3aS,5S,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-2-acetyloxy-4,5-dimethylspiro[9-oxatricyclo[6.2.2.01,6]dodecane-11,2'-oxirane]-10-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: b77c5bc3-9cbc-403d-a3e4-656ac45e38c1
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: [(1R,2S,4R,5S,6R,8R,10R,11R)-5-[(2S,3aS,5S,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-2-acetyloxy-4,5-dimethylspiro[9-oxatricyclo[6.2.2.01,6]dodecane-11,2'-oxirane]-10-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C23C(CC(O1)CC24CO4)C(C(CC3OC(=O)C)C)(C)C5CC6CC(OC6O5)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1[C@@]23[C@H](C[C@@H](O1)C[C@]24CO4)[C@@]([C@@H](C[C@@H]3OC(=O)C)C)(C)[C@@H]5C[C@H]6C[C@H](O[C@H]6O5)O
• InChI: InChI=1S/C27H38O9/c1-6-13(2)22(30)36-24-27-18(10-17(33-24)11-26(27)12-31-26)25(5,14(3)7-20(27)32-15(4)28)19-8-16-9-21(29)35-23(16)34-19/h6,14,16-21,23-24,29H,7-12H2,1-5H3/b13-6+/t14-,16+,17-,18-,19+,20+,21+,23-,24-,25+,26+,27+/m1/s1
• InChI Key: DBRRHXZMVDOQTA-CZHUZJGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₉
• Molecular Weight: 506.60 g/mol
• Exact Mass: 506.25158279 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.6716	67.16%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7986	79.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8839	88.39%
OATP1B3 inhibitior	+	0.9185	91.85%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5271	52.71%
P-glycoprotein inhibitior	+	0.6202	62.02%
P-glycoprotein substrate	+	0.5160	51.60%
CYP3A4 substrate	+	0.6955	69.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8792	87.92%
CYP3A4 inhibition	-	0.6069	60.69%
CYP2C9 inhibition	-	0.8390	83.90%
CYP2C19 inhibition	-	0.8834	88.34%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.8404	84.04%
CYP2C8 inhibition	+	0.5591	55.91%
CYP inhibitory promiscuity	-	0.8759	87.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5391	53.91%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.5787	57.87%
Skin corrosion	-	0.9302	93.02%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5569	55.69%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8411	84.11%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7964	79.64%
Acute Oral Toxicity (c)	I	0.7386	73.86%
Estrogen receptor binding	+	0.8830	88.30%
Androgen receptor binding	+	0.6462	64.62%
Thyroid receptor binding	+	0.6019	60.19%
Glucocorticoid receptor binding	+	0.7252	72.52%
Aromatase binding	+	0.7872	78.72%
PPAR gamma	+	0.7646	76.46%
Honey bee toxicity	-	0.6575	65.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	96.27%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.76%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.00%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	91.67%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.57%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.18%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.41%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.65%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.20%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.50%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.53%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.45%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.14%	95.56%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.43%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.05%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.63%	89.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.60%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.17%	82.69%

Plants that contains it

• Scutellaria cypria

Cross-Links

• PubChem: 100934967
• LOTUS: LTS0109324
• wikiData: Q104974753