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(1S,2S,4S,5R,8R,9R,10S,13S,14R,18R,20S)-10-[(2R,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-2-yl]oxy-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-9,20-bis(hydroxymethyl)-4,5,9,13-tetramethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-ene-20-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 4ad778a8-6c81-49a9-9e5f-d434320a446e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (1S,2S,4S,5R,8R,9R,10S,13S,14R,18R,20S)-10-[(2R,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-2-yl]oxy-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-9,20-bis(hydroxymethyl)-4,5,9,13-tetramethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-ene-20-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(CO)C(=O)O)CO6)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)OS(=O)(=O)O)O)O)O
SMILES (Isomeric) C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=CC56[C@]4(C[C@@H]([C@@]7([C@H]5C[C@@](CC7)(CO)C(=O)O)CO6)O)C)C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)OS(=O)(=O)O)O)O)O
InChI InChI=1S/C48H76O24S/c1-21-29(54)36(70-39-34(59)32(57)35(23(17-50)68-39)72-73(62,63)64)37(71-38-33(58)31(56)30(55)22(16-49)67-38)40(66-21)69-28-8-9-42(2)24(43(28,3)18-51)6-10-44(4)25(42)7-11-48-26-14-46(19-52,41(60)61)12-13-47(26,20-65-48)27(53)15-45(44,48)5/h7,11,21-40,49-59H,6,8-10,12-20H2,1-5H3,(H,60,61)(H,62,63,64)/t21-,22-,23-,24-,25-,26-,27+,28+,29+,30-,31+,32-,33-,34-,35-,36+,37-,38+,39+,40+,42+,43+,44-,45+,46+,47-,48?/m1/s1
InChI Key CSRCIYUDELHALE-RRQSMBEVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C48H76O24S
Molecular Weight 1069.20 g/mol
Exact Mass 1068.44472446 g/mol
Topological Polar Surface Area (TPSA) 396.00 Ų
XlogP -2.70
Atomic LogP (AlogP) -2.53
H-Bond Acceptor 22
H-Bond Donor 13
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2S,4S,5R,8R,9R,10S,13S,14R,18R,20S)-10-[(2R,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-2-yl]oxy-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-9,20-bis(hydroxymethyl)-4,5,9,13-tetramethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-ene-20-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 + 0.7351 73.51%
Caco-2 - 0.8761 87.61%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.4767 47.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8310 83.10%
OATP1B3 inhibitior + 0.9293 92.93%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.7693 76.93%
P-glycoprotein inhibitior + 0.7475 74.75%
P-glycoprotein substrate + 0.6833 68.33%
CYP3A4 substrate + 0.7403 74.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8671 86.71%
CYP3A4 inhibition - 0.8113 81.13%
CYP2C9 inhibition - 0.7868 78.68%
CYP2C19 inhibition - 0.7326 73.26%
CYP2D6 inhibition - 0.8832 88.32%
CYP1A2 inhibition - 0.7552 75.52%
CYP2C8 inhibition + 0.7678 76.78%
CYP inhibitory promiscuity - 0.9396 93.96%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.5700 57.00%
Carcinogenicity (trinary) Non-required 0.5804 58.04%
Eye corrosion - 0.9746 97.46%
Eye irritation - 0.9011 90.11%
Skin irritation - 0.7532 75.32%
Skin corrosion - 0.9073 90.73%
Ames mutagenesis - 0.7170 71.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6870 68.70%
Micronuclear + 0.5500 55.00%
Hepatotoxicity - 0.5762 57.62%
skin sensitisation - 0.8534 85.34%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.7798 77.98%
Acute Oral Toxicity (c) III 0.5593 55.93%
Estrogen receptor binding + 0.7622 76.22%
Androgen receptor binding + 0.7618 76.18%
Thyroid receptor binding - 0.5106 51.06%
Glucocorticoid receptor binding + 0.7025 70.25%
Aromatase binding + 0.6292 62.92%
PPAR gamma + 0.7767 77.67%
Honey bee toxicity - 0.6378 63.78%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9836 98.36%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.21% 96.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 94.77% 97.36%
CHEMBL226 P30542 Adenosine A1 receptor 94.37% 95.93%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 94.33% 96.38%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.62% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.23% 91.11%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 90.15% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.34% 89.00%
CHEMBL2581 P07339 Cathepsin D 87.61% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.38% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.91% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 86.56% 92.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.89% 96.00%
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 85.65% 92.78%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.53% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.98% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.82% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.39% 94.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 83.97% 91.24%
CHEMBL1914 P06276 Butyrylcholinesterase 82.74% 95.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.21% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.54% 99.23%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.43% 96.90%
CHEMBL5028 O14672 ADAM10 81.12% 97.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.98% 94.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.79% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.45% 93.04%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.00% 95.83%

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.
Bupleurum rigidum

Cross-Links

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PubChem 163187448
LOTUS LTS0090512
wikiData Q104969509