[(E)-2-cyano-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 05a7b0e5-71bd-4cbe-a011-c0f690081a50
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: [(E)-2-cyano-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC(=CCOC2C(C(C(C(O2)CO)O)O)O)C#N)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OC/C(=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C#N)O
• InChI: InChI=1S/C20H23NO9/c21-9-13(11-29-16(24)6-3-12-1-4-14(23)5-2-12)7-8-28-20-19(27)18(26)17(25)15(10-22)30-20/h1-7,15,17-20,22-23,25-27H,8,10-11H2/b6-3+,13-7+/t15-,17-,18+,19-,20-/m1/s1
• InChI Key: CUXBICPZQSXIEU-UWJUNBCGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₉
• Molecular Weight: 421.40 g/mol
• Exact Mass: 421.13728131 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.78
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6280	62.80%
Caco-2	-	0.9043	90.43%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7419	74.19%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5998	59.98%
P-glycoprotein inhibitior	-	0.7146	71.46%
P-glycoprotein substrate	-	0.8689	86.89%
CYP3A4 substrate	+	0.5945	59.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.8763	87.63%
CYP2C9 inhibition	-	0.7950	79.50%
CYP2C19 inhibition	-	0.7820	78.20%
CYP2D6 inhibition	-	0.8769	87.69%
CYP1A2 inhibition	-	0.7778	77.78%
CYP2C8 inhibition	+	0.7298	72.98%
CYP inhibitory promiscuity	-	0.5094	50.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6335	63.35%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9346	93.46%
Skin irritation	-	0.8118	81.18%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5208	52.08%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8000	80.00%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5609	56.09%
Acute Oral Toxicity (c)	III	0.5499	54.99%
Estrogen receptor binding	+	0.7026	70.26%
Androgen receptor binding	+	0.6838	68.38%
Thyroid receptor binding	+	0.5685	56.85%
Glucocorticoid receptor binding	-	0.5787	57.87%
Aromatase binding	+	0.6088	60.88%
PPAR gamma	+	0.7721	77.21%
Honey bee toxicity	-	0.7382	73.82%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.8223	82.23%

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	95.96%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.47%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.10%	96.09%
CHEMBL3194	P02766	Transthyretin	91.13%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.43%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.00%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.93%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.71%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.21%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	84.96%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.43%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.93%	91.71%
CHEMBL2581	P07339	Cathepsin D	80.80%	98.95%

Plants that contains it

• Aconitum violaceum
• Codonopsis pilosula
• Delphinium shawurense
• Fagraea gracilipes
• Garcinia xipshuanbannaensis
• Gutierrezia microcephala
• Helichrysum graveolens
• Iryanthera paraensis
• Lathyrus nissolia
• Leonurus persicus
• Magnolia sieboldii
• Peltogyne floribunda
• Ratibida mexicana
• Ribes nigrum

Cross-Links

• PubChem: 11972423
• NPASS: NPC178026
• LOTUS: LTS0055413
• wikiData: Q104970554