Smilaside K

Details

• Internal ID: 61a028ac-0c66-45fc-94b2-7709f764e438
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OC2(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)OC)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)COC(=O)C=CC5=CC=C(C=C5)O)CO)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)COC(=O)/C=C/C5=CC=C(C=C5)O)CO)O)O
• InChI: InChI=1S/C43H46O20/c1-23(45)59-40-39(54)37(52)32(20-44)60-42(40)63-43(22-58-35(50)15-8-24-4-11-27(46)12-5-24)41(61-36(51)17-10-26-7-14-29(48)31(19-26)56-3)38(53)33(62-43)21-57-34(49)16-9-25-6-13-28(47)30(18-25)55-2/h4-19,32-33,37-42,44,46-48,52-54H,20-22H2,1-3H3/b15-8+,16-9+,17-10+/t32-,33-,37-,38-,39+,40-,41+,42-,43+/m1/s1
• InChI Key: JFUNTNHRWXZULB-OVPSZRCZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₆O₂₀
• Molecular Weight: 882.80 g/mol
• Exact Mass: 882.25824385 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 20
• H-Bond Donor: 7
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7827	78.27%
Caco-2	-	0.8779	87.79%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7023	70.23%
OATP2B1 inhibitior	+	0.5573	55.73%
OATP1B1 inhibitior	+	0.8167	81.67%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9083	90.83%
P-glycoprotein inhibitior	+	0.7607	76.07%
P-glycoprotein substrate	-	0.5509	55.09%
CYP3A4 substrate	+	0.6838	68.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.7802	78.02%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.8158	81.58%
CYP2D6 inhibition	-	0.9296	92.96%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	+	0.8195	81.95%
CYP inhibitory promiscuity	-	0.7421	74.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9102	91.02%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8107	81.07%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8235	82.35%
Acute Oral Toxicity (c)	III	0.6316	63.16%
Estrogen receptor binding	+	0.8304	83.04%
Androgen receptor binding	+	0.7193	71.93%
Thyroid receptor binding	+	0.6156	61.56%
Glucocorticoid receptor binding	+	0.6874	68.74%
Aromatase binding	+	0.5680	56.80%
PPAR gamma	+	0.7559	75.59%
Honey bee toxicity	-	0.6712	67.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9374	93.74%

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	99.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.62%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.22%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.46%	96.00%
CHEMBL3194	P02766	Transthyretin	94.70%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.19%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.28%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.29%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.09%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.87%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.58%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.38%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.54%	91.19%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	85.75%	97.03%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.46%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.31%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.16%	89.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.87%	89.67%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.73%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.19%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	82.59%	92.50%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.65%	93.10%
CHEMBL2581	P07339	Cathepsin D	81.25%	98.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.23%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.23%	91.07%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.22%	99.15%

Plants that contains it

• Ageratina adenophora
• Boehmeria nivea
• Crotalaria micans
• Croton poilanei
• Dasymaschalon sootepense
• Dictyoloma vandellianum
• Euonymus sachalinensis
• Felicia erigeroides
• Flueggea virosa subsp. melanthesoides
• Guatteria megalophylla
• Lupinus paniculatus
• Lycoris traubii
• Lygodium flexuosum
• Panax ginseng
• Saccharum spontaneum
• Smilax bracteata
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 24862643
• NPASS: NPC6278
• LOTUS: LTS0088436
• wikiData: Q105127032