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(1S,4aS)-7-(benzoyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,6-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

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 3d516075-923c-4442-9645-860ba99d6c0a
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (1S,4aS)-7-(benzoyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,6-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) C1CC(=C2C1C(=COC2OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O)C(=O)O)COC(=O)C5=CC=CC=C5
SMILES (Isomeric) C1CC(=C2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O)O)O)O)C(=O)O)COC(=O)C5=CC=CC=C5
InChI InChI=1S/C28H34O15/c29-16-10-40-27(22(33)19(16)30)41-11-17-20(31)21(32)23(34)28(42-17)43-26-18-13(6-7-14(18)15(9-39-26)24(35)36)8-38-25(37)12-4-2-1-3-5-12/h1-5,9,14,16-17,19-23,26-34H,6-8,10-11H2,(H,35,36)/t14-,16+,17-,19+,20-,21+,22-,23-,26+,27+,28+/m1/s1
InChI Key ACYSRUVVWAZOEU-RWNJOILESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H34O15
Molecular Weight 610.60 g/mol
Exact Mass 610.18977037 g/mol
Topological Polar Surface Area (TPSA) 231.00 Ų
XlogP -2.70
Atomic LogP (AlogP) -1.85
H-Bond Acceptor 14
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS)-7-(benzoyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,6-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5961 59.61%
Caco-2 - 0.9036 90.36%
Blood Brain Barrier - 0.5542 55.42%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8351 83.51%
OATP2B1 inhibitior - 0.8541 85.41%
OATP1B1 inhibitior + 0.8496 84.96%
OATP1B3 inhibitior + 0.9485 94.85%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.5959 59.59%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.6440 64.40%
CYP3A4 substrate + 0.6578 65.78%
CYP2C9 substrate - 0.6054 60.54%
CYP2D6 substrate - 0.8723 87.23%
CYP3A4 inhibition - 0.8675 86.75%
CYP2C9 inhibition - 0.9033 90.33%
CYP2C19 inhibition - 0.7824 78.24%
CYP2D6 inhibition - 0.8530 85.30%
CYP1A2 inhibition - 0.7685 76.85%
CYP2C8 inhibition + 0.7611 76.11%
CYP inhibitory promiscuity - 0.9314 93.14%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6292 62.92%
Eye corrosion - 0.9864 98.64%
Eye irritation - 0.9221 92.21%
Skin irritation - 0.7745 77.45%
Skin corrosion - 0.9567 95.67%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8059 80.59%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.8652 86.52%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.8987 89.87%
Acute Oral Toxicity (c) III 0.4472 44.72%
Estrogen receptor binding + 0.8100 81.00%
Androgen receptor binding + 0.6102 61.02%
Thyroid receptor binding - 0.5052 50.52%
Glucocorticoid receptor binding - 0.4795 47.95%
Aromatase binding + 0.5608 56.08%
PPAR gamma + 0.6869 68.69%
Honey bee toxicity - 0.7856 78.56%
Biodegradation - 0.5750 57.50%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9390 93.90%

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
CHEMBL221 P23219 Cyclooxygenase-1 95.36% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.02% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.54% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.81% 97.09%
CHEMBL2581 P07339 Cathepsin D 92.42% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.68% 99.17%
CHEMBL226 P30542 Adenosine A1 receptor 89.60% 95.93%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.44% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.31% 99.23%
CHEMBL3891 P07384 Calpain 1 85.03% 93.04%
CHEMBL2179 P04062 Beta-glucocerebrosidase 84.87% 85.31%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 84.40% 83.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.00% 95.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.30% 95.89%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 81.51% 87.67%
CHEMBL5255 O00206 Toll-like receptor 4 80.83% 92.50%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 80.77% 95.64%
CHEMBL3401 O75469 Pregnane X receptor 80.26% 94.73%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 21579241
LOTUS LTS0181567
wikiData Q104909397