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Smilaside D

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 68e6945f-2a14-4b4d-b63a-c908fd2e4678
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-acetyloxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-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) CC(=O)OC1C(OC(C1OC(=O)C=CC2=CC(=C(C=C2)O)OC)(COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)COC(=O)C=CC5=CC(=C(C=C5)O)OC
SMILES (Isomeric) CC(=O)O[C@@H]1[C@H](O[C@@]([C@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)OC)(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)COC(=O)/C=C/C5=CC(=C(C=C5)O)OC
InChI InChI=1S/C43H46O20/c1-23(45)59-40-33(21-57-34(49)16-9-25-6-13-28(47)30(18-25)55-2)62-43(63-42-39(54)38(53)37(52)32(20-44)60-42,22-58-35(50)15-8-24-4-11-27(46)12-5-24)41(40)61-36(51)17-10-26-7-14-29(48)31(19-26)56-3/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 NWHZEENLJLTZEU-RJISVSAVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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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

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CHEMBL490680

2D Structure

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2D Structure of Smilaside D

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7827 78.27%
Caco-2 - 0.8771 87.71%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7023 70.23%
OATP2B1 inhibitior + 0.5558 55.58%
OATP1B1 inhibitior + 0.8315 83.15%
OATP1B3 inhibitior + 0.9459 94.59%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9548 95.48%
P-glycoprotein inhibitior + 0.7696 76.96%
P-glycoprotein substrate - 0.5726 57.26%
CYP3A4 substrate + 0.6891 68.91%
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 + 0.8199 81.99%
CYP inhibitory promiscuity - 0.7421 74.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6433 64.33%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.9108 91.08%
Skin irritation - 0.8527 85.27%
Skin corrosion - 0.9546 95.46%
Ames mutagenesis - 0.7300 73.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8193 81.93%
Micronuclear - 0.5426 54.26%
Hepatotoxicity - 0.8875 88.75%
skin sensitisation - 0.8251 82.51%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.8418 84.18%
Acute Oral Toxicity (c) III 0.6316 63.16%
Estrogen receptor binding + 0.8306 83.06%
Androgen receptor binding + 0.7056 70.56%
Thyroid receptor binding + 0.6026 60.26%
Glucocorticoid receptor binding + 0.7133 71.33%
Aromatase binding + 0.5324 53.24%
PPAR gamma + 0.7415 74.15%
Honey bee toxicity - 0.6558 65.58%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9374 93.74%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.64% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.07% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.94% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.69% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.50% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.86% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 91.85% 94.73%
CHEMBL4208 P20618 Proteasome component C5 91.34% 90.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.21% 99.17%
CHEMBL3194 P02766 Transthyretin 89.98% 90.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.85% 94.45%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.60% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.06% 85.14%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.90% 89.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.88% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 84.85% 91.19%
CHEMBL3714130 P46095 G-protein coupled receptor 6 84.73% 97.36%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.39% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.48% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 80.77% 92.50%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.72% 85.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.69% 89.67%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.16% 94.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.00% 97.28%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Smilax china
Smilax glabra

Cross-Links

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PubChem 11593149
NPASS NPC28651
LOTUS LTS0260399
wikiData Q105186614