(3S,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

Details

• Internal ID: ed80cf63-7d3c-442c-8fef-4fbc27029f3b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-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(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C=CC1[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@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C22H32O14/c1-2-8-9-3-4-31-19(30)10(9)6-32-20(8)36-22-18(29)16(27)14(25)12(35-22)7-33-21-17(28)15(26)13(24)11(5-23)34-21/h2,6,8-9,11-18,20-29H,1,3-5,7H2/t8?,9-,11+,12+,13+,14+,15-,16-,17+,18+,20-,21+,22-/m0/s1
• InChI Key: LILOLDYAQAFVGN-HQKKLDBESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₁₄
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.17920569 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.77
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6190	61.90%
Caco-2	-	0.8882	88.82%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7627	76.27%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8550	85.50%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8689	86.89%
P-glycoprotein inhibitior	-	0.7088	70.88%
P-glycoprotein substrate	-	0.8575	85.75%
CYP3A4 substrate	+	0.6128	61.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8602	86.02%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.8660	86.60%
CYP2C19 inhibition	-	0.8277	82.77%
CYP2D6 inhibition	-	0.8774	87.74%
CYP1A2 inhibition	-	0.8514	85.14%
CYP2C8 inhibition	-	0.6035	60.35%
CYP inhibitory promiscuity	-	0.8641	86.41%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6851	68.51%
Eye corrosion	-	0.9805	98.05%
Eye irritation	-	0.9361	93.61%
Skin irritation	-	0.7821	78.21%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6537	65.37%
Micronuclear	-	0.7741	77.41%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6072	60.72%
Acute Oral Toxicity (c)	III	0.4512	45.12%
Estrogen receptor binding	+	0.6894	68.94%
Androgen receptor binding	+	0.5633	56.33%
Thyroid receptor binding	-	0.4937	49.37%
Glucocorticoid receptor binding	-	0.6133	61.33%
Aromatase binding	+	0.6183	61.83%
PPAR gamma	+	0.6449	64.49%
Honey bee toxicity	-	0.7824	78.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4064	40.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	95.75%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.66%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.72%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.04%	83.57%
CHEMBL226	P30542	Adenosine A1 receptor	89.21%	95.93%
CHEMBL220	P22303	Acetylcholinesterase	88.38%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.18%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.97%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.63%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.20%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.07%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.56%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	81.42%	94.73%

Plants that contains it

• Gentiana olivieri

Cross-Links

• PubChem: 11968964
• LOTUS: LTS0248835
• wikiData: Q105152252