Smilaside F

Details

• Internal ID: 45449af9-5020-4266-8f2d-b57555be94c6
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-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)OCC1C(C(C(C(O1)OC2(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)OC(=O)C)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[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)OC(=O)C)O)O
• InChI: InChI=1S/C44H46O20/c1-24(45)57-21-33-38(53)40(55)41(60-25(2)46)43(61-33)64-44(23-59-36(51)17-9-26-4-12-29(47)13-5-26)42(62-37(52)19-10-27-6-14-30(48)15-7-27)39(54)34(63-44)22-58-35(50)18-11-28-8-16-31(49)32(20-28)56-3/h4-20,33-34,38-43,47-49,53-55H,21-23H2,1-3H3/b17-9+,18-11+,19-10+/t33-,34-,38-,39-,40+,41-,42+,43-,44+/m1/s1
• InChI Key: QHZJEIGSGZHOHS-ZSXKYDPFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₄₆O₂₀
• Molecular Weight: 894.80 g/mol
• Exact Mass: 894.25824385 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 20
• H-Bond Donor: 6
• Rotatable Bonds: 17

Synonyms

• CHEMBL500983

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5827	58.27%
Caco-2	-	0.8748	87.48%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	+	0.5584	55.84%
OATP1B1 inhibitior	+	0.8292	82.92%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9325	93.25%
P-glycoprotein inhibitior	+	0.7609	76.09%
P-glycoprotein substrate	-	0.5524	55.24%
CYP3A4 substrate	+	0.6845	68.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8739	87.39%
CYP2C9 inhibition	-	0.7917	79.17%
CYP2C19 inhibition	-	0.7730	77.30%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.8133	81.33%
CYP2C8 inhibition	+	0.8370	83.70%
CYP inhibitory promiscuity	-	0.7862	78.62%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6408	64.08%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.8471	84.71%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7493	74.93%
Micronuclear	-	0.5152	51.52%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8260	82.60%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8594	85.94%
Acute Oral Toxicity (c)	III	0.5955	59.55%
Estrogen receptor binding	+	0.8485	84.85%
Androgen receptor binding	+	0.7160	71.60%
Thyroid receptor binding	+	0.6140	61.40%
Glucocorticoid receptor binding	+	0.6920	69.20%
Aromatase binding	+	0.5578	55.78%
PPAR gamma	+	0.7679	76.79%
Honey bee toxicity	-	0.6885	68.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9847	98.47%

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	98.63%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.23%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.02%	96.00%
CHEMBL3194	P02766	Transthyretin	94.55%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.99%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.27%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.03%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.91%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.95%	97.21%
CHEMBL4208	P20618	Proteasome component C5	89.46%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.52%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.12%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.50%	89.62%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	86.14%	97.03%
CHEMBL340	P08684	Cytochrome P450 3A4	85.70%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	84.86%	91.49%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.72%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.49%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.03%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.85%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.39%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.23%	82.50%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.09%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.89%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%

Plants that contains it

• Smilax china

Cross-Links

• PubChem: 11658000
• NPASS: NPC215095
• LOTUS: LTS0018173
• wikiData: Q105221230