(4R,4aR,6S,7R,7aS)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-4,7-dimethyl-4a,5,6,7a-tetrahydro-4H-cyclopenta[b]pyran-3-one

Details

• Internal ID: dcdbf3a1-3828-4d5e-9401-b4d233461c32
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (4R,4aR,6S,7R,7aS)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-4,7-dimethyl-4a,5,6,7a-tetrahydro-4H-cyclopenta[b]pyran-3-one
• SMILES (Canonical): CC1C2CC(C(C2OCC1=O)(C)O)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@@H]([C@@]([C@H]2OCC1=O)(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O
• InChI: InChI=1S/C21H34O13/c1-8-9-3-12(20(2,28)17(9)30-4-10(8)23)34-18-15(26)14(25)13(24)11(33-18)5-31-19-16(27)21(29,6-22)7-32-19/h8-9,11-19,22,24-29H,3-7H2,1-2H3/t8-,9-,11-,12+,13-,14+,15-,16+,17+,18+,19-,20-,21-/m1/s1
• InChI Key: KQSPLYKGVKSJHQ-PCHLGBRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₁₃
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.19994113 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -3.99
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5163	51.63%
Caco-2	-	0.8675	86.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6281	62.81%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8550	85.50%
P-glycoprotein inhibitior	-	0.7110	71.10%
P-glycoprotein substrate	-	0.5661	56.61%
CYP3A4 substrate	+	0.6853	68.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8705	87.05%
CYP3A4 inhibition	-	0.9426	94.26%
CYP2C9 inhibition	-	0.9562	95.62%
CYP2C19 inhibition	-	0.9336	93.36%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9212	92.12%
CYP2C8 inhibition	-	0.6478	64.78%
CYP inhibitory promiscuity	-	0.9503	95.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6807	68.07%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9577	95.77%
Skin irritation	-	0.7700	77.00%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.5024	50.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7039	70.39%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5782	57.82%
skin sensitisation	-	0.9111	91.11%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4839	48.39%
Acute Oral Toxicity (c)	I	0.5820	58.20%
Estrogen receptor binding	+	0.7389	73.89%
Androgen receptor binding	+	0.5492	54.92%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.7246	72.46%
PPAR gamma	+	0.5445	54.45%
Honey bee toxicity	-	0.7448	74.48%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.4396	43.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	97.74%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.84%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.80%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.66%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.81%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.79%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.43%	99.23%
CHEMBL5957	P21589	5'-nucleotidase	85.30%	97.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.83%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.78%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.36%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.16%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.77%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.84%	94.45%
CHEMBL2581	P07339	Cathepsin D	81.28%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.79%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.36%	96.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.31%	95.83%

Plants that contains it

• Patrinia scabra

Cross-Links

• PubChem: 163006729
• LOTUS: LTS0180088
• wikiData: Q105144771