bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2S)-2-[(2S,3R,4R,5S,6R)-6-(acetyloxymethyl)-3,4-dihydroxy-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-2-[(2R)-butan-2-yl]butanedioate

Details

Top
Internal ID eb000235-a269-481b-8ae8-d56fd1431fe8
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2S)-2-[(2S,3R,4R,5S,6R)-6-(acetyloxymethyl)-3,4-dihydroxy-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-2-[(2R)-butan-2-yl]butanedioate
SMILES (Canonical) CCC(C)C(CC(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)(C(=O)OCC3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)COC(=O)C)OC(=O)C=CC6=CC=CC=C6)O)O
SMILES (Isomeric) CC[C@@H](C)[C@@](CC(=O)OCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C(=O)OCC3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)OC(=O)/C=C/C6=CC=CC=C6)O)O
InChI InChI=1S/C51H64O24/c1-4-26(2)51(50(65)68-24-30-12-17-32(18-13-30)70-48-44(63)41(60)39(58)34(22-53)72-48,20-37(56)67-23-29-10-15-31(16-11-29)69-47-43(62)40(59)38(57)33(21-52)71-47)75-49-45(64)42(61)46(35(73-49)25-66-27(3)54)74-36(55)19-14-28-8-6-5-7-9-28/h5-19,26,33-35,38-49,52-53,57-64H,4,20-25H2,1-3H3/b19-14+/t26-,33-,34-,35-,38-,39-,40+,41+,42-,43-,44-,45-,46-,47-,48-,49+,51+/m1/s1
InChI Key CCZOYJFTCPEQLK-JKHCJQOLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C51H64O24
Molecular Weight 1061.00 g/mol
Exact Mass 1060.37875290 g/mol
Topological Polar Surface Area (TPSA) 363.00 Ų
XlogP 0.60
Atomic LogP (AlogP) -1.34
H-Bond Acceptor 24
H-Bond Donor 10
Rotatable Bonds 22

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2S)-2-[(2S,3R,4R,5S,6R)-6-(acetyloxymethyl)-3,4-dihydroxy-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-2-[(2R)-butan-2-yl]butanedioate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5473 54.73%
Caco-2 - 0.8641 86.41%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8857 88.57%
Subcellular localzation Mitochondria 0.7995 79.95%
OATP2B1 inhibitior - 0.7302 73.02%
OATP1B1 inhibitior + 0.8276 82.76%
OATP1B3 inhibitior + 0.8621 86.21%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.9642 96.42%
P-glycoprotein inhibitior + 0.7450 74.50%
P-glycoprotein substrate + 0.5209 52.09%
CYP3A4 substrate + 0.6917 69.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8866 88.66%
CYP3A4 inhibition - 0.6190 61.90%
CYP2C9 inhibition - 0.8533 85.33%
CYP2C19 inhibition - 0.8328 83.28%
CYP2D6 inhibition - 0.9416 94.16%
CYP1A2 inhibition - 0.8478 84.78%
CYP2C8 inhibition + 0.7540 75.40%
CYP inhibitory promiscuity - 0.8801 88.01%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6565 65.65%
Eye corrosion - 0.9918 99.18%
Eye irritation - 0.9008 90.08%
Skin irritation - 0.8055 80.55%
Skin corrosion - 0.9562 95.62%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7982 79.82%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.8895 88.95%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.9265 92.65%
Acute Oral Toxicity (c) III 0.5758 57.58%
Estrogen receptor binding + 0.7784 77.84%
Androgen receptor binding + 0.7224 72.24%
Thyroid receptor binding + 0.6366 63.66%
Glucocorticoid receptor binding + 0.7417 74.17%
Aromatase binding - 0.5133 51.33%
PPAR gamma + 0.7864 78.64%
Honey bee toxicity - 0.6243 62.43%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9953 99.53%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.56% 96.09%
CHEMBL2581 P07339 Cathepsin D 97.40% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 97.23% 90.17%
CHEMBL3060 Q9Y345 Glycine transporter 2 95.52% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.50% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.92% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 94.89% 96.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 92.92% 94.62%
CHEMBL3401 O75469 Pregnane X receptor 92.16% 94.73%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 91.75% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.33% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.39% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.39% 89.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 86.27% 94.08%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.97% 95.89%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 84.88% 96.95%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.64% 93.00%
CHEMBL209 P07477 Trypsin I 82.98% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.50% 95.89%

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.
Gymnadenia conopsea

Cross-Links

Top
PubChem 154496702
LOTUS LTS0184423
wikiData Q104953981