(4aS)-5beta-Ethenyl-6alpha-[6-O-[2-hydroxy-3-(beta-D-glucopyranosyloxy)benzoyl]-beta-D-glucopyranosyloxy]-4,4aalpha,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one

Details

• Internal ID: e9ca59bf-063f-499f-8f72-37a3007a9d3b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• SMILES (Canonical): C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)COC(=O)C4=C(C(=CC=C4)OC5C(C(C(C(O5)CO)O)O)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)COC(=O)C4=C(C(=CC=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O17/c1-2-11-12-6-7-40-26(39)14(12)9-42-27(11)46-29-24(37)22(35)20(33)17(45-29)10-41-25(38)13-4-3-5-15(18(13)31)43-28-23(36)21(34)19(32)16(8-30)44-28/h2-5,9,11-12,16-17,19-24,27-37H,1,6-8,10H2/t11-,12+,16-,17-,19-,20-,21+,22+,23-,24-,27+,28-,29+/m1/s1
• InChI Key: MSGQZIQHABSCGP-HKUJKWCKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₇
• Molecular Weight: 656.60 g/mol
• Exact Mass: 656.19524968 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.84
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5056	50.56%
Caco-2	-	0.8886	88.86%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6687	66.87%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8290	82.90%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5639	56.39%
P-glycoprotein inhibitior	+	0.6077	60.77%
P-glycoprotein substrate	-	0.6077	60.77%
CYP3A4 substrate	+	0.6791	67.91%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	-	0.8656	86.56%
CYP3A4 inhibition	-	0.8860	88.60%
CYP2C9 inhibition	-	0.6861	68.61%
CYP2C19 inhibition	-	0.6945	69.45%
CYP2D6 inhibition	-	0.8506	85.06%
CYP1A2 inhibition	-	0.7615	76.15%
CYP2C8 inhibition	+	0.7527	75.27%
CYP inhibitory promiscuity	-	0.8190	81.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6835	68.35%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6438	64.38%
Micronuclear	-	0.6067	60.67%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7727	77.27%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5892	58.92%
Acute Oral Toxicity (c)	III	0.4838	48.38%
Estrogen receptor binding	+	0.7548	75.48%
Androgen receptor binding	+	0.5843	58.43%
Thyroid receptor binding	-	0.5565	55.65%
Glucocorticoid receptor binding	-	0.4830	48.30%
Aromatase binding	-	0.4940	49.40%
PPAR gamma	+	0.6980	69.80%
Honey bee toxicity	-	0.7815	78.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9133	91.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.82%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.36%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.86%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.03%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.03%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.21%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.04%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.54%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.97%	96.21%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.85%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.34%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.63%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.31%	91.24%
CHEMBL3891	P07384	Calpain 1	85.28%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.99%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.43%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.79%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.13%	94.45%

Plants that contains it

• Nitraria tangutorum

Cross-Links

• PubChem: 49802965
• NPASS: NPC278943