Smilaside H

Details

• Internal ID: 585c5929-db23-4dc5-aa6f-090af6dafdae
• 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-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-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)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)COC(=O)/C=C/C5=CC=C(C=C5)O)CO)O)O
• InChI: InChI=1S/C42H44O19/c1-23(44)57-39-38(53)36(51)31(20-43)58-41(39)61-42(22-56-34(49)16-8-24-3-11-27(45)12-4-24)40(59-35(50)18-9-25-5-13-28(46)14-6-25)37(52)32(60-42)21-55-33(48)17-10-26-7-15-29(47)30(19-26)54-2/h3-19,31-32,36-41,43,45-47,51-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37-,38+,39-,40+,41-,42+/m1/s1
• InChI Key: LVFWZZFIRQCFMJ-DYUFTDJRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₄O₁₉
• Molecular Weight: 852.80 g/mol
• Exact Mass: 852.24767917 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 19
• H-Bond Donor: 7
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7932	79.32%
Caco-2	-	0.8839	88.39%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7226	72.26%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.8167	81.67%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9386	93.86%
P-glycoprotein inhibitior	+	0.7499	74.99%
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	-	0.7733	77.33%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.7818	78.18%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	-	0.8862	88.62%
CYP2C8 inhibition	+	0.8195	81.95%
CYP inhibitory promiscuity	-	0.7325	73.25%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6680	66.80%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9120	91.20%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8397	83.97%
Micronuclear	-	0.5326	53.26%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8034	80.34%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8235	82.35%
Acute Oral Toxicity (c)	III	0.6640	66.40%
Estrogen receptor binding	+	0.8466	84.66%
Androgen receptor binding	+	0.7075	70.75%
Thyroid receptor binding	+	0.5926	59.26%
Glucocorticoid receptor binding	+	0.6665	66.65%
Aromatase binding	+	0.5508	55.08%
PPAR gamma	+	0.7438	74.38%
Honey bee toxicity	-	0.6712	67.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9363	93.63%

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: 24862644
• NPASS: NPC106565
• LOTUS: LTS0154092
• wikiData: Q105157836