[(2R,3S,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-3-hydroxy-3'-(4-hydroxyphenyl)-5,5'-dioxospiro[3,3a-dihydro-2H-furo[3,2-b]furan-6,2'-oxolane]-6a-yl]oxy-3-acetyloxy-4,5-dihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: cd320e1a-cf8b-4e55-9c71-74a45487e7fc
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(2R,3S,4R,5R,6S)-6-[(3S,3'R,3aR,6S,6aR)-3-hydroxy-3'-(4-hydroxyphenyl)-5,5'-dioxospiro[3,3a-dihydro-2H-furo[3,2-b]furan-6,2'-oxolane]-6a-yl]oxy-3-acetyloxy-4,5-dihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC23C(C(CO2)O)OC(=O)C34C(CC(=O)O4)C5=CC=C(C=C5)O)O)O)OC(=O)C
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@]23[C@@H]([C@H](CO2)O)OC(=O)[C@]34[C@H](CC(=O)O4)C5=CC=C(C=C5)O)O)O)OC(=O)C
• InChI: InChI=1S/C25H28O15/c1-10(26)34-9-16-20(36-11(2)27)18(31)19(32)22(37-16)40-25-21(15(29)8-35-25)38-23(33)24(25)14(7-17(30)39-24)12-3-5-13(28)6-4-12/h3-6,14-16,18-22,28-29,31-32H,7-9H2,1-2H3/t14-,15+,16-,18-,19-,20-,21-,22+,24-,25-/m1/s1
• InChI Key: QHPQAHUEQHZVON-RPAYLAIVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₅
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.14282018 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.87
• H-Bond Acceptor: 15
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8514	85.14%
Caco-2	-	0.8628	86.28%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7716	77.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8239	82.39%
OATP1B3 inhibitior	+	0.9098	90.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8502	85.02%
P-glycoprotein inhibitior	+	0.6408	64.08%
P-glycoprotein substrate	-	0.5773	57.73%
CYP3A4 substrate	+	0.6867	68.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8677	86.77%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8504	85.04%
CYP2C19 inhibition	-	0.8238	82.38%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.9249	92.49%
CYP2C8 inhibition	+	0.5591	55.91%
CYP inhibitory promiscuity	-	0.8235	82.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5150	51.50%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.7859	78.59%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6060	60.60%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.5412	54.12%
skin sensitisation	-	0.8654	86.54%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6084	60.84%
Acute Oral Toxicity (c)	III	0.6079	60.79%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.7100	71.00%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5913	59.13%
Aromatase binding	+	0.5456	54.56%
PPAR gamma	+	0.6799	67.99%
Honey bee toxicity	-	0.7590	75.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9040	90.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.15%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.10%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.69%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.62%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	95.50%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.68%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.51%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.41%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.96%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.83%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.06%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.67%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.49%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	87.49%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.07%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.81%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.73%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.48%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.26%	94.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.62%	93.10%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.31%	85.00%

Plants that contains it

• Ficus racemosa

Cross-Links

• PubChem: 162884218
• LOTUS: LTS0210663
• wikiData: Q105276451