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[(2S,3R,4S,5R,6R)-5-[(E)-but-2-enoyl]oxy-3-[(2R,3S,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4R,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxolan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

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 0af79b31-a40a-4c7b-b666-e8e3f949ba89
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name [(2S,3R,4S,5R,6R)-5-[(E)-but-2-enoyl]oxy-3-[(2R,3S,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4R,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxolan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
SMILES (Canonical) CC=CC(=O)OC1C(OC(C(C1O)OC2C(C(C(C(O2)C)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)C)O)O)O)O)O)O)OC(=O)C56CCC(CC5C7=CCC8C(C7(CC6O)C)(CCC9C8(CC(C(C9(C)CO)OC1C(C(C(C(O1)CO)O)O)O)O)C)C)(C)C)C
SMILES (Isomeric) C/C=C/C(=O)O[C@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3[C@@H]([C@H]([C@H](O3)CO)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)O)O)O)O)O)OC(=O)[C@]56CCC(C[C@H]5C7=CC[C@H]8[C@]([C@@]7(C[C@H]6O)C)(CC[C@@H]9[C@@]8(C[C@@H]([C@@H]([C@@]9(C)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C)C)(C)C)C
InChI InChI=1S/C63H100O28/c1-11-12-36(69)86-48-27(4)83-56(50(45(48)78)89-53-44(77)41(74)47(26(3)82-53)87-55-46(79)49(32(23-65)85-55)88-52-42(75)39(72)37(70)25(2)81-52)91-57(80)63-18-17-58(5,6)19-29(63)28-13-14-34-59(7)20-30(67)51(90-54-43(76)40(73)38(71)31(22-64)84-54)60(8,24-66)33(59)15-16-61(34,9)62(28,10)21-35(63)68/h11-13,25-27,29-35,37-56,64-68,70-79H,14-24H2,1-10H3/b12-11+/t25-,26-,27-,29+,30+,31-,32-,33-,34-,35-,37-,38-,39+,40+,41-,42+,43-,44+,45+,46-,47-,48+,49+,50-,51+,52-,53-,54+,55+,56+,59+,60+,61-,62-,63-/m1/s1
InChI Key XEJHWIFLGZTKGN-HOVCFWIISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C63H100O28
Molecular Weight 1305.40 g/mol
Exact Mass 1304.64011253 g/mol
Topological Polar Surface Area (TPSA) 439.00 Ų
XlogP -0.50
Atomic LogP (AlogP) -2.45
H-Bond Acceptor 28
H-Bond Donor 15
Rotatable Bonds 15

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3R,4S,5R,6R)-5-[(E)-but-2-enoyl]oxy-3-[(2R,3S,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4R,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxolan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8427 84.27%
Caco-2 - 0.8663 86.63%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.8733 87.33%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7555 75.55%
OATP1B3 inhibitior + 0.8381 83.81%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5250 52.50%
BSEP inhibitior + 0.9716 97.16%
P-glycoprotein inhibitior + 0.7435 74.35%
P-glycoprotein substrate + 0.6332 63.32%
CYP3A4 substrate + 0.7390 73.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8875 88.75%
CYP3A4 inhibition - 0.8187 81.87%
CYP2C9 inhibition - 0.8372 83.72%
CYP2C19 inhibition - 0.9259 92.59%
CYP2D6 inhibition - 0.9408 94.08%
CYP1A2 inhibition - 0.9133 91.33%
CYP2C8 inhibition + 0.7721 77.21%
CYP inhibitory promiscuity - 0.9476 94.76%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4689 46.89%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.8973 89.73%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9368 93.68%
Ames mutagenesis - 0.7932 79.32%
Human Ether-a-go-go-Related Gene inhibition + 0.7486 74.86%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.8727 87.27%
skin sensitisation - 0.9098 90.98%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.8031 80.31%
Acute Oral Toxicity (c) III 0.6742 67.42%
Estrogen receptor binding + 0.7386 73.86%
Androgen receptor binding + 0.7545 75.45%
Thyroid receptor binding + 0.6942 69.42%
Glucocorticoid receptor binding + 0.8356 83.56%
Aromatase binding + 0.6471 64.71%
PPAR gamma + 0.8451 84.51%
Honey bee toxicity - 0.6499 64.99%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9692 96.92%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.16% 91.11%
CHEMBL3714130 P46095 G-protein coupled receptor 6 97.81% 97.36%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.23% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.53% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.78% 97.25%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.28% 96.61%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.93% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.76% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.43% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.15% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.14% 100.00%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 87.28% 91.65%
CHEMBL1937 Q92769 Histone deacetylase 2 86.77% 94.75%
CHEMBL3401 O75469 Pregnane X receptor 85.78% 94.73%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.15% 91.07%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 84.68% 87.67%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.80% 81.11%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 82.62% 89.34%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.60% 95.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.16% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.85% 94.00%
CHEMBL5028 O14672 ADAM10 81.83% 97.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.38% 94.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.36% 86.92%

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 163033355
LOTUS LTS0040623
wikiData Q105326378