(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-[5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indol-3-yl]ethyl]prop-2-enamide

Details

• Internal ID: cb97de2d-e33e-489c-bcec-dfcede87967a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-[5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indol-3-yl]ethyl]prop-2-enamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CNC3=C2C=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H30N2O9/c1-35-20-10-14(2-6-19(20)30)3-7-22(31)27-9-8-15-12-28-18-5-4-16(11-17(15)18)36-26-25(34)24(33)23(32)21(13-29)37-26/h2-7,10-12,21,23-26,28-30,32-34H,8-9,13H2,1H3,(H,27,31)/b7-3+/t21-,23-,24+,25-,26-/m1/s1
• InChI Key: RZBNXMNICVMBNE-JWMPNCEXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀N₂O₉
• Molecular Weight: 514.50 g/mol
• Exact Mass: 514.19513054 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.43
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8088	80.88%
Caco-2	-	0.8957	89.57%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Nucleus	0.4195	41.95%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8888	88.88%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9032	90.32%
P-glycoprotein inhibitior	+	0.6298	62.98%
P-glycoprotein substrate	+	0.6072	60.72%
CYP3A4 substrate	+	0.6691	66.91%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.7681	76.81%
CYP2C9 inhibition	-	0.6771	67.71%
CYP2C19 inhibition	-	0.7760	77.60%
CYP2D6 inhibition	-	0.7279	72.79%
CYP1A2 inhibition	-	0.7378	73.78%
CYP2C8 inhibition	+	0.7479	74.79%
CYP inhibitory promiscuity	-	0.5737	57.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5879	58.79%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9521	95.21%
Skin irritation	-	0.7843	78.43%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6955	69.55%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.8823	88.23%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9410	94.10%
Acute Oral Toxicity (c)	III	0.6749	67.49%
Estrogen receptor binding	+	0.6935	69.35%
Androgen receptor binding	-	0.4885	48.85%
Thyroid receptor binding	+	0.5519	55.19%
Glucocorticoid receptor binding	+	0.6300	63.00%
Aromatase binding	-	0.5313	53.13%
PPAR gamma	+	0.6841	68.41%
Honey bee toxicity	-	0.7724	77.24%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.7943	79.43%

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	99.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.27%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.21%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.52%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.17%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.60%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.01%	98.95%
CHEMBL4208	P20618	Proteasome component C5	90.90%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.00%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.24%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.57%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.84%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	84.59%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	84.41%	94.73%
CHEMBL2535	P11166	Glucose transporter	83.82%	98.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.52%	94.33%
CHEMBL255	P29275	Adenosine A2b receptor	82.78%	98.59%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.22%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.92%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.05%	86.92%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.59%	92.88%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 101933130
• LOTUS: LTS0142504
• wikiData: Q105248305