[(1R,2R,3R,5R,6S,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate

Details

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Internal ID f6ee92ac-9ad5-4738-9b05-51d09e2a6f0a
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name [(1R,2R,3R,5R,6S,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
SMILES (Canonical) CC12C3(CC4C3(C(O1)CC4(O2)O)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) C[C@]12[C@]3(C[C@@H]4[C@]3([C@H](O1)C[C@@]4(O2)O)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C23H28O11/c1-20-23(33-19-17(27)16(26)15(25)12(9-24)31-19)7-13-21(23,14(32-20)8-22(13,29)34-20)10-30-18(28)11-5-3-2-4-6-11/h2-6,12-17,19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15-,16+,17-,19+,20+,21+,22+,23+/m1/s1
InChI Key NIBHZLGVFHPVFJ-SCLBYUEBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H28O11
Molecular Weight 480.50 g/mol
Exact Mass 480.16316171 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -1.36
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2R,3R,5R,6S,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6225 62.25%
Caco-2 - 0.8233 82.33%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.5954 59.54%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9203 92.03%
OATP1B3 inhibitior + 0.9581 95.81%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.5981 59.81%
P-glycoprotein inhibitior - 0.6367 63.67%
P-glycoprotein substrate - 0.7752 77.52%
CYP3A4 substrate + 0.6534 65.34%
CYP2C9 substrate - 0.8039 80.39%
CYP2D6 substrate - 0.8544 85.44%
CYP3A4 inhibition - 0.9025 90.25%
CYP2C9 inhibition - 0.9192 91.92%
CYP2C19 inhibition - 0.8121 81.21%
CYP2D6 inhibition - 0.9335 93.35%
CYP1A2 inhibition - 0.8949 89.49%
CYP2C8 inhibition + 0.5571 55.71%
CYP inhibitory promiscuity - 0.9463 94.63%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6002 60.02%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9544 95.44%
Skin irritation - 0.7617 76.17%
Skin corrosion - 0.9454 94.54%
Ames mutagenesis - 0.6370 63.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4411 44.11%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7699 76.99%
skin sensitisation - 0.8876 88.76%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.7839 78.39%
Acute Oral Toxicity (c) III 0.3692 36.92%
Estrogen receptor binding + 0.8344 83.44%
Androgen receptor binding + 0.7010 70.10%
Thyroid receptor binding + 0.6513 65.13%
Glucocorticoid receptor binding + 0.5732 57.32%
Aromatase binding + 0.7858 78.58%
PPAR gamma + 0.7745 77.45%
Honey bee toxicity - 0.8395 83.95%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.8802 88.02%

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 95.45% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.14% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.98% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.56% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.01% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 89.81% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.44% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 84.82% 95.93%
CHEMBL2581 P07339 Cathepsin D 82.93% 98.95%
CHEMBL5028 O14672 ADAM10 82.60% 97.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.47% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 82.28% 94.73%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.69% 95.83%
CHEMBL4208 P20618 Proteasome component C5 80.79% 90.00%

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.
Paeonia suffruticosa

Cross-Links

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PubChem 101863447
NPASS NPC176325