(3S,4S,4aS)-3-[(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-4-ethenyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

Details

• Internal ID: fa0c8071-f07b-418a-8f2a-a6d3a109264e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4S,4aS)-3-[(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-4-ethenyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• SMILES (Canonical): C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): C=C[C@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[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/C21H30O13/c1-2-9-10-3-4-29-17(27)11(10)5-30-18(9)34-19-15(25)14(24)13(23)12(33-19)6-31-20-16(26)21(28,7-22)8-32-20/h2,5,9-10,12-16,18-20,22-26,28H,1,3-4,6-8H2/t9-,10-,12+,13+,14-,15+,16-,18-,19-,20+,21+/m0/s1
• InChI Key: JNPXCTROEJQHKD-KAZAEUKGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₁₃
• Molecular Weight: 490.50 g/mol
• Exact Mass: 490.16864101 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.13
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6201	62.01%
Caco-2	-	0.8880	88.80%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7838	78.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8749	87.49%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8372	83.72%
P-glycoprotein inhibitior	-	0.6862	68.62%
P-glycoprotein substrate	-	0.7099	70.99%
CYP3A4 substrate	+	0.6673	66.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.9331	93.31%
CYP2C9 inhibition	-	0.8878	88.78%
CYP2C19 inhibition	-	0.8392	83.92%
CYP2D6 inhibition	-	0.8756	87.56%
CYP1A2 inhibition	-	0.8835	88.35%
CYP2C8 inhibition	+	0.5487	54.87%
CYP inhibitory promiscuity	-	0.9201	92.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6145	61.45%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9381	93.81%
Skin irritation	-	0.7158	71.58%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7574	75.74%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6091	60.91%
skin sensitisation	-	0.8476	84.76%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6325	63.25%
Acute Oral Toxicity (c)	III	0.4481	44.81%
Estrogen receptor binding	+	0.6462	64.62%
Androgen receptor binding	+	0.5739	57.39%
Thyroid receptor binding	-	0.5224	52.24%
Glucocorticoid receptor binding	-	0.5754	57.54%
Aromatase binding	+	0.6088	60.88%
PPAR gamma	+	0.6425	64.25%
Honey bee toxicity	-	0.7482	74.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7174	71.74%

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	97.50%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.38%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.22%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	93.82%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.56%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.27%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.24%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.83%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.61%	94.45%
CHEMBL5957	P21589	5'-nucleotidase	84.42%	97.78%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.35%	95.83%
CHEMBL220	P22303	Acetylcholinesterase	83.37%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.26%	97.25%
CHEMBL4530	P00488	Coagulation factor XIII	82.67%	96.00%
CHEMBL2581	P07339	Cathepsin D	82.35%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.87%	94.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.16%	96.00%

Plants that contains it

• Carapichea ipecacuanha
• Lonicera quinquelocularis

Cross-Links

• PubChem: 162967459
• LOTUS: LTS0199305
• wikiData: Q105132062