Smilaside B

Details

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Internal ID bf19a1bf-7f61-4c94-842b-a1bcb94a29d7
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name [(2R,3R,4S,5S)-5-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-(hydroxymethyl)oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)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)CO)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)CO)CO)O)O
InChI InChI=1S/C34H40O18/c1-17(37)48-31-30(44)28(42)24(14-35)49-33(31)52-34(16-36)32(50-27(41)11-7-19-5-9-21(39)23(13-19)46-3)29(43)25(51-34)15-47-26(40)10-6-18-4-8-20(38)22(12-18)45-2/h4-13,24-25,28-33,35-36,38-39,42-44H,14-16H2,1-3H3/b10-6+,11-7+/t24-,25-,28-,29-,30+,31-,32+,33-,34+/m1/s1
InChI Key XLHWVVGQWRFHPR-LCYVLNELSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C34H40O18
Molecular Weight 736.70 g/mol
Exact Mass 736.22146442 g/mol
Topological Polar Surface Area (TPSA) 267.00 Ų
XlogP 0.10
Atomic LogP (AlogP) -0.87
H-Bond Acceptor 18
H-Bond Donor 7
Rotatable Bonds 14

Synonyms

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CHEMBL475478

2D Structure

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2D Structure of Smilaside B

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 - 0.8877 88.77%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7023 70.23%
OATP2B1 inhibitior - 0.7198 71.98%
OATP1B1 inhibitior + 0.8329 83.29%
OATP1B3 inhibitior + 0.9459 94.59%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8848 88.48%
P-glycoprotein inhibitior + 0.7142 71.42%
P-glycoprotein substrate - 0.6331 63.31%
CYP3A4 substrate + 0.6623 66.23%
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 + 0.7265 72.65%
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 - 0.9210 92.10%
Skin irritation - 0.8527 85.27%
Skin corrosion - 0.9546 95.46%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8512 85.12%
Micronuclear - 0.5426 54.26%
Hepatotoxicity - 0.8324 83.24%
skin sensitisation - 0.8251 82.51%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.8544 85.44%
Acute Oral Toxicity (c) III 0.6316 63.16%
Estrogen receptor binding + 0.8310 83.10%
Androgen receptor binding + 0.6648 66.48%
Thyroid receptor binding + 0.5653 56.53%
Glucocorticoid receptor binding + 0.6939 69.39%
Aromatase binding + 0.5747 57.47%
PPAR gamma + 0.7539 75.39%
Honey bee toxicity - 0.7171 71.71%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
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 99.73% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.45% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.15% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.98% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.47% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.78% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.63% 89.00%
CHEMBL3194 P02766 Transthyretin 92.27% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.77% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 91.41% 91.49%
CHEMBL3401 O75469 Pregnane X receptor 90.68% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.76% 99.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.30% 95.50%
CHEMBL4208 P20618 Proteasome component C5 84.68% 90.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.85% 97.36%
CHEMBL340 P08684 Cytochrome P450 3A4 82.67% 91.19%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.82% 86.92%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.65% 92.62%
CHEMBL5255 O00206 Toll-like receptor 4 80.51% 92.50%

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 11629132
NPASS NPC216819
LOTUS LTS0235516
wikiData Q105329995