(E)-3-(4-hydroxyphenyl)-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: ced2b41a-2523-42e0-a217-92495975e3d3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (E)-3-(4-hydroxyphenyl)-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): C1=CC(=CC=C1C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=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/C25H28N2O8/c28-13-20-22(31)23(32)24(33)25(35-20)34-17-6-7-19-18(11-17)15(12-27-19)9-10-26-21(30)8-3-14-1-4-16(29)5-2-14/h1-8,11-12,20,22-25,27-29,31-33H,9-10,13H2,(H,26,30)/b8-3+/t20-,22-,23+,24-,25-/m1/s1
• InChI Key: LPGWQGDUKIPAME-IQTAGMQYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈N₂O₈
• Molecular Weight: 484.50 g/mol
• Exact Mass: 484.18456586 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7976	79.76%
Caco-2	-	0.8889	88.89%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4295	42.95%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8880	88.80%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8922	89.22%
P-glycoprotein inhibitior	+	0.5960	59.60%
P-glycoprotein substrate	+	0.5161	51.61%
CYP3A4 substrate	+	0.6544	65.44%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8480	84.80%
CYP3A4 inhibition	-	0.8379	83.79%
CYP2C9 inhibition	-	0.8169	81.69%
CYP2C19 inhibition	-	0.8358	83.58%
CYP2D6 inhibition	-	0.7633	76.33%
CYP1A2 inhibition	-	0.7744	77.44%
CYP2C8 inhibition	+	0.7404	74.04%
CYP inhibitory promiscuity	-	0.5884	58.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6108	61.08%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9515	95.15%
Skin irritation	-	0.7865	78.65%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7283	72.83%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8872	88.72%
Acute Oral Toxicity (c)	III	0.6321	63.21%
Estrogen receptor binding	+	0.7167	71.67%
Androgen receptor binding	+	0.5946	59.46%
Thyroid receptor binding	-	0.5262	52.62%
Glucocorticoid receptor binding	+	0.6252	62.52%
Aromatase binding	-	0.5506	55.06%
PPAR gamma	+	0.6892	68.92%
Honey bee toxicity	-	0.7421	74.21%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.7396	73.96%

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	99.92%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.46%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.34%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.88%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.78%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.03%	96.00%
CHEMBL2581	P07339	Cathepsin D	92.90%	98.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	91.80%	94.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.48%	89.67%
CHEMBL255	P29275	Adenosine A2b receptor	90.01%	98.59%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.64%	91.71%
CHEMBL1937	Q92769	Histone deacetylase 2	88.74%	94.75%
CHEMBL4208	P20618	Proteasome component C5	87.97%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.83%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.04%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.00%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.62%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.24%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	85.14%	94.73%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.34%	89.44%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.78%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.26%	85.00%
CHEMBL4530	P00488	Coagulation factor XIII	81.13%	96.00%
CHEMBL3959	P16083	Quinone reductase 2	80.62%	89.49%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.34%	85.31%

Plants that contains it

• Carthamus tinctorius
• Ipomoea obscura

Cross-Links

• PubChem: 44200708
• LOTUS: LTS0196449
• wikiData: Q105155166