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[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]oxan-3-yl] 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzoate

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 41fa284a-efc0-4b16-9bac-2e64fd174c80
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
IUPAC Name [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]oxan-3-yl] 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C41H52O25/c1-5-18-19-9-10-55-36(53)21(19)12-57-38(18)66-41-35(60-17(4)45)34(59-16(3)44)33(25(64-41)14-56-15(2)43)65-37(54)20-7-6-8-22(26(20)46)61-40-32(52)30(50)28(48)24(63-40)13-58-39-31(51)29(49)27(47)23(11-42)62-39/h5-8,12,18-19,23-25,27-35,38-42,46-52H,1,9-11,13-14H2,2-4H3/t18-,19+,23-,24-,25-,27-,28-,29+,30+,31-,32-,33-,34+,35-,38+,39-,40-,41+/m1/s1
InChI Key KSEGFPBHGPMGNK-JRIGLBGXSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C41H52O25
Molecular Weight 944.80 g/mol
Exact Mass 944.27976714 g/mol
Topological Polar Surface Area (TPSA) 358.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -3.31
H-Bond Acceptor 25
H-Bond Donor 8
Rotatable Bonds 15

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]oxan-3-yl] 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6676 66.76%
Caco-2 - 0.8687 86.87%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7036 70.36%
OATP2B1 inhibitior - 0.8638 86.38%
OATP1B1 inhibitior + 0.8035 80.35%
OATP1B3 inhibitior + 0.8917 89.17%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.9117 91.17%
P-glycoprotein inhibitior + 0.7381 73.81%
P-glycoprotein substrate + 0.5513 55.13%
CYP3A4 substrate + 0.7200 72.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8835 88.35%
CYP3A4 inhibition - 0.9060 90.60%
CYP2C9 inhibition - 0.7661 76.61%
CYP2C19 inhibition - 0.7726 77.26%
CYP2D6 inhibition - 0.8831 88.31%
CYP1A2 inhibition - 0.6942 69.42%
CYP2C8 inhibition + 0.7910 79.10%
CYP inhibitory promiscuity - 0.8321 83.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7134 71.34%
Eye corrosion - 0.9866 98.66%
Eye irritation - 0.9036 90.36%
Skin irritation - 0.7536 75.36%
Skin corrosion - 0.9385 93.85%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6987 69.87%
Micronuclear - 0.6767 67.67%
Hepatotoxicity - 0.6875 68.75%
skin sensitisation - 0.8249 82.49%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity + 0.6831 68.31%
Acute Oral Toxicity (c) III 0.5871 58.71%
Estrogen receptor binding + 0.8457 84.57%
Androgen receptor binding + 0.6552 65.52%
Thyroid receptor binding + 0.5610 56.10%
Glucocorticoid receptor binding + 0.7189 71.89%
Aromatase binding + 0.5817 58.17%
PPAR gamma + 0.7936 79.36%
Honey bee toxicity - 0.7136 71.36%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9626 96.26%

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
CHEMBL220 P22303 Acetylcholinesterase 97.35% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.45% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.39% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.79% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.55% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.07% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.26% 95.89%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.02% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.20% 95.56%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 92.08% 94.80%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.75% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.83% 89.00%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 87.60% 95.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.73% 94.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.22% 91.24%
CHEMBL5255 O00206 Toll-like receptor 4 84.87% 92.50%
CHEMBL3401 O75469 Pregnane X receptor 84.75% 94.73%
CHEMBL340 P08684 Cytochrome P450 3A4 83.84% 91.19%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 83.06% 82.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 83.01% 83.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.70% 96.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.36% 96.21%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.10% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.15% 94.33%

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.
Gentiana linearis

Cross-Links

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PubChem 162963878
LOTUS LTS0254708
wikiData Q105145377