(5r,6s)-5-Ethenyl-4a-hydroxy-6-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[5,4-c]pyran-1-one

Details

• Internal ID: 3ef781de-ebd7-4b6b-8d79-7570f6378964
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4R)-4-ethenyl-4a-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)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)CO)O)O)O
• SMILES (Isomeric): C=C[C@H]1[C@@H](OC=C2C1(CCOC2=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H22O10/c1-2-7-14(24-6-8-13(21)23-4-3-16(7,8)22)26-15-12(20)11(19)10(18)9(5-17)25-15/h2,6-7,9-12,14-15,17-20,22H,1,3-5H2/t7-,9+,10+,11-,12+,14-,15-,16?/m0/s1
• InChI Key: HEYZWPRKKUGDCR-MQADLURCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34 g/mol
• Exact Mass: 374.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.48
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• (5r,6s)-5-ethenyl-4a-hydroxy-6-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[5,4-c]pyran-1-one
• Swertiamarin (6CI,7CI,8CI)
• LS-127487
• 5beta-Ethenyl-6alpha-(beta-D-glucopyranosyloxy)-4a-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5500	55.00%
Caco-2	-	0.8615	86.15%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7442	74.42%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8600	86.00%
OATP1B3 inhibitior	+	0.9072	90.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8346	83.46%
BSEP inhibitior	-	0.8412	84.12%
P-glycoprotein inhibitior	-	0.8792	87.92%
P-glycoprotein substrate	-	0.8797	87.97%
CYP3A4 substrate	+	0.6161	61.61%
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	-	0.7452	74.52%
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	-	0.9227	92.27%
Skin irritation	-	0.7428	74.28%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6560	65.60%
Micronuclear	-	0.7741	77.41%
Hepatotoxicity	-	0.7066	70.66%
skin sensitisation	-	0.8275	82.75%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6120	61.20%
Acute Oral Toxicity (c)	III	0.5149	51.49%
Estrogen receptor binding	-	0.5582	55.82%
Androgen receptor binding	-	0.4831	48.31%
Thyroid receptor binding	+	0.5930	59.30%
Glucocorticoid receptor binding	-	0.5078	50.78%
Aromatase binding	+	0.6324	63.24%
PPAR gamma	+	0.6662	66.62%
Honey bee toxicity	-	0.6420	64.20%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
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	97.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.99%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.35%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.95%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.93%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.61%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.60%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.38%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.04%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.68%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.53%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.36%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.11%	92.62%
CHEMBL220	P22303	Acetylcholinesterase	80.01%	94.45%

Plants that contains it

• Centaurium erythraea
• Cornus officinalis
• Gentiana crassicaulis
• Gentiana dahurica
• Gentiana lutea
• Gentiana macrophylla
• Gentiana straminea
• Ixanthus viscosus

Cross-Links

• PubChem: 114700
• NPASS: NPC15924
• LOTUS: LTS0276435
• wikiData: Q105027158