[2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxyphenyl]methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

Details

Top
Internal ID 1353074c-537e-49f9-b2f5-9cfb4e59a9c0
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name [2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxyphenyl]methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate
SMILES (Canonical) C1CC(=O)C(C=C1)(C(=O)OCC2=CC=CC=C2OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=CC=C4)O
SMILES (Isomeric) C1CC(=O)[C@](C=C1)(C(=O)OCC2=CC=CC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C/C4=CC=CC=C4)O
InChI InChI=1S/C29H30O11/c30-16-21-24(33)25(34)26(40-23(32)14-13-18-8-2-1-3-9-18)27(39-21)38-20-11-5-4-10-19(20)17-37-28(35)29(36)15-7-6-12-22(29)31/h1-5,7-11,13-15,21,24-27,30,33-34,36H,6,12,16-17H2/b14-13+/t21-,24-,25+,26-,27-,29-/m1/s1
InChI Key KREPPVUFKQQVNS-WZEISIENSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C29H30O11
Molecular Weight 554.50 g/mol
Exact Mass 554.17881177 g/mol
Topological Polar Surface Area (TPSA) 169.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 0.82
H-Bond Acceptor 11
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxyphenyl]methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7521 75.21%
Caco-2 - 0.9028 90.28%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7364 73.64%
OATP2B1 inhibitior - 0.7042 70.42%
OATP1B1 inhibitior + 0.8854 88.54%
OATP1B3 inhibitior + 0.9432 94.32%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.8197 81.97%
P-glycoprotein inhibitior + 0.6983 69.83%
P-glycoprotein substrate - 0.6822 68.22%
CYP3A4 substrate + 0.6636 66.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8718 87.18%
CYP3A4 inhibition - 0.8466 84.66%
CYP2C9 inhibition - 0.6066 60.66%
CYP2C19 inhibition - 0.7786 77.86%
CYP2D6 inhibition - 0.9237 92.37%
CYP1A2 inhibition - 0.8878 88.78%
CYP2C8 inhibition + 0.6773 67.73%
CYP inhibitory promiscuity - 0.8510 85.10%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.6660 66.60%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9149 91.49%
Skin irritation - 0.8406 84.06%
Skin corrosion - 0.9480 94.80%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6586 65.86%
Micronuclear - 0.6267 62.67%
Hepatotoxicity - 0.6302 63.02%
skin sensitisation - 0.8305 83.05%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.8103 81.03%
Acute Oral Toxicity (c) III 0.6525 65.25%
Estrogen receptor binding + 0.7573 75.73%
Androgen receptor binding + 0.6743 67.43%
Thyroid receptor binding - 0.5069 50.69%
Glucocorticoid receptor binding + 0.6117 61.17%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.6511 65.11%
Honey bee toxicity - 0.7269 72.69%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.8688 86.88%

Targets

Top

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 99.49% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.95% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.57% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.04% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.80% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.18% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.28% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.64% 95.50%
CHEMBL221 P23219 Cyclooxygenase-1 88.12% 90.17%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 87.51% 94.23%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.72% 95.83%
CHEMBL226 P30542 Adenosine A1 receptor 85.30% 95.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.88% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.82% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.13% 91.07%
CHEMBL2581 P07339 Cathepsin D 82.91% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.01% 99.17%

Plants that contains it

Top
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.
Salix sericea

Cross-Links

Top
PubChem 162893377
LOTUS LTS0119907
wikiData Q105144952