Smilaside G

Details

• Internal ID: 19429bc6-4ad1-4f33-a622-1b2481298f6e
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4R,5R)-4-hydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(O2)(COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C=CC5=CC=C(C=C5)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@](O2)(COC(=O)/C=C/C3=CC=C(C=C3)O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O)O)O
• InChI: InChI=1S/C40H42O18/c1-52-28-18-24(6-14-27(28)44)9-16-31(45)53-20-30-35(49)38(56-33(47)17-8-23-4-12-26(43)13-5-23)40(57-30,58-39-37(51)36(50)34(48)29(19-41)55-39)21-54-32(46)15-7-22-2-10-25(42)11-3-22/h2-18,29-30,34-39,41-44,48-51H,19-21H2,1H3/b15-7+,16-9+,17-8+/t29-,30-,34-,35-,36+,37-,38+,39-,40+/m1/s1
• InChI Key: AKRPKXVYRNFNPZ-QVHYGTEESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₂O₁₈
• Molecular Weight: 810.70 g/mol
• Exact Mass: 810.23711449 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7896	78.96%
Caco-2	-	0.8911	89.11%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7330	73.30%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8492	84.92%
OATP1B3 inhibitior	+	0.9647	96.47%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9104	91.04%
P-glycoprotein inhibitior	+	0.7136	71.36%
P-glycoprotein substrate	-	0.6294	62.94%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8175	81.75%
CYP2C9 inhibition	-	0.8078	80.78%
CYP2C19 inhibition	-	0.7609	76.09%
CYP2D6 inhibition	-	0.9190	91.90%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	+	0.8414	84.14%
CYP inhibitory promiscuity	-	0.7424	74.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6241	62.41%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9145	91.45%
Skin irritation	-	0.8494	84.94%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8142	81.42%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8167	81.67%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8765	87.65%
Acute Oral Toxicity (c)	III	0.6819	68.19%
Estrogen receptor binding	+	0.8268	82.68%
Androgen receptor binding	+	0.6914	69.14%
Thyroid receptor binding	+	0.5597	55.97%
Glucocorticoid receptor binding	+	0.6479	64.79%
Aromatase binding	-	0.4881	48.81%
PPAR gamma	+	0.7107	71.07%
Honey bee toxicity	-	0.6955	69.55%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9224	92.24%

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	99.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.53%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.39%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.17%	95.56%
CHEMBL3194	P02766	Transthyretin	93.13%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.19%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.11%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.27%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.80%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.68%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.12%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.75%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.66%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.36%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	83.04%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.78%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.25%	89.67%
CHEMBL2535	P11166	Glucose transporter	80.89%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.89%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.43%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%

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
• Smilax china
• Smilax glabra
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 24862591
• NPASS: NPC110110
• LOTUS: LTS0170057
• wikiData: Q104913804