(3S,4R,4aR)-4-ethenyl-4a-hydroxy-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-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one

Details

• Internal ID: f4a184b4-67f9-4029-9425-2db0e14e0902
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4R,4aR)-4-ethenyl-4a-hydroxy-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-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one
• SMILES (Canonical): C=CC1C(OC=C2C1(CCOC2=O)O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C=C[C@H]1[C@@H](OC=C2[C@]1(CCOC2=O)O)O[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/C22H32O15/c1-2-8-19(33-6-9-18(30)32-4-3-22(8,9)31)37-21-17(29)15(27)13(25)11(36-21)7-34-20-16(28)14(26)12(24)10(5-23)35-20/h2,6,8,10-17,19-21,23-29,31H,1,3-5,7H2/t8-,10+,11+,12+,13+,14-,15-,16+,17+,19-,20+,21-,22+/m0/s1
• InChI Key: GMEODWUOLDADIG-VLZCNBGRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₁₅
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -4.65
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5500	55.00%
Caco-2	-	0.8905	89.05%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7442	74.42%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	+	0.9072	90.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8346	83.46%
BSEP inhibitior	-	0.8141	81.41%
P-glycoprotein inhibitior	-	0.6431	64.31%
P-glycoprotein substrate	-	0.8065	80.65%
CYP3A4 substrate	+	0.6451	64.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.9242	92.42%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.8247	82.47%
CYP2D6 inhibition	-	0.8783	87.83%
CYP1A2 inhibition	-	0.8799	87.99%
CYP2C8 inhibition	-	0.6452	64.52%
CYP inhibitory promiscuity	-	0.9281	92.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6412	64.12%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.7428	74.28%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6723	67.23%
Micronuclear	-	0.7741	77.41%
Hepatotoxicity	-	0.7316	73.16%
skin sensitisation	-	0.8275	82.75%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5645	56.45%
Acute Oral Toxicity (c)	III	0.5149	51.49%
Estrogen receptor binding	+	0.6346	63.46%
Androgen receptor binding	+	0.5474	54.74%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5226	52.26%
Aromatase binding	+	0.6648	66.48%
PPAR gamma	+	0.6231	62.31%
Honey bee toxicity	-	0.6526	65.26%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.5067	50.67%

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	97.77%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.87%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.46%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.31%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.03%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.76%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.04%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.85%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.33%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.53%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.07%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	80.94%	95.93%
CHEMBL220	P22303	Acetylcholinesterase	80.25%	94.45%

Plants that contains it

• Swertia japonica

Cross-Links

• PubChem: 101273518
• NPASS: NPC256542
• LOTUS: LTS0154203
• wikiData: Q105011730