(1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid

Details

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Internal ID 1d66b12c-39a0-4296-9744-39b7c959aecd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC4CCC5(C6CCC7C8C(CCC8(CCC7(C6(CCC5C4(C)C(=O)O)C)C)C(=O)O)C(=C)C)C)O)O)O)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)O[C@H]4CC[C@@]5([C@H]6CC[C@@H]7[C@H]8[C@@H](CC[C@@]8(CC[C@]7([C@@]6(CC[C@H]5[C@]4(C)C(=O)O)C)C)C(=O)O)C(=C)C)C)O)O)O)CO)O)O)O
InChI InChI=1S/C48H76O19/c1-20(2)22-10-15-48(43(60)61)17-16-45(5)23(29(22)48)8-9-26-44(4)13-12-28(47(7,42(58)59)27(44)11-14-46(26,45)6)66-41-36(56)33(53)31(51)25(65-41)19-62-39-37(57)34(54)38(24(18-49)64-39)67-40-35(55)32(52)30(50)21(3)63-40/h21-41,49-57H,1,8-19H2,2-7H3,(H,58,59)(H,60,61)/t21-,22-,23+,24+,25+,26+,27+,28-,29+,30-,31+,32+,33-,34+,35+,36+,37+,38+,39+,40-,41-,44+,45+,46+,47-,48-/m0/s1
InChI Key FCFVJTWUSARYOA-OIISTEDZSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C48H76O19
Molecular Weight 957.10 g/mol
Exact Mass 956.49808019 g/mol
Topological Polar Surface Area (TPSA) 312.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 0.65
H-Bond Acceptor 17
H-Bond Donor 11
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6096 60.96%
Caco-2 - 0.8827 88.27%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8115 81.15%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8601 86.01%
OATP1B3 inhibitior + 0.8498 84.98%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6048 60.48%
BSEP inhibitior + 0.8943 89.43%
P-glycoprotein inhibitior + 0.7460 74.60%
P-glycoprotein substrate - 0.5073 50.73%
CYP3A4 substrate + 0.7272 72.72%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.9079 90.79%
CYP2C9 inhibition - 0.9014 90.14%
CYP2C19 inhibition - 0.9100 91.00%
CYP2D6 inhibition - 0.9530 95.30%
CYP1A2 inhibition - 0.8903 89.03%
CYP2C8 inhibition + 0.7269 72.69%
CYP inhibitory promiscuity - 0.9446 94.46%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6732 67.32%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9050 90.50%
Skin irritation - 0.5122 51.22%
Skin corrosion - 0.9403 94.03%
Ames mutagenesis - 0.7024 70.24%
Human Ether-a-go-go-Related Gene inhibition + 0.7696 76.96%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.7598 75.98%
skin sensitisation - 0.9225 92.25%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8481 84.81%
Acute Oral Toxicity (c) III 0.4375 43.75%
Estrogen receptor binding + 0.8242 82.42%
Androgen receptor binding + 0.7489 74.89%
Thyroid receptor binding - 0.5301 53.01%
Glucocorticoid receptor binding + 0.6966 69.66%
Aromatase binding + 0.6660 66.60%
PPAR gamma + 0.7991 79.91%
Honey bee toxicity - 0.5941 59.41%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9810 98.10%

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 95.17% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.01% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.57% 96.61%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.42% 86.33%
CHEMBL233 P35372 Mu opioid receptor 91.58% 97.93%
CHEMBL3714130 P46095 G-protein coupled receptor 6 90.55% 97.36%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 88.67% 96.09%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 88.56% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.75% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.44% 89.00%
CHEMBL2581 P07339 Cathepsin D 87.35% 98.95%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.15% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 86.69% 91.19%
CHEMBL5255 O00206 Toll-like receptor 4 86.18% 92.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.90% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.25% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.10% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.73% 92.94%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.67% 93.04%
CHEMBL226 P30542 Adenosine A1 receptor 83.13% 95.93%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 82.90% 96.38%
CHEMBL5028 O14672 ADAM10 82.37% 97.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.11% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.11% 100.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.09% 95.83%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.63% 99.17%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.60% 100.00%
CHEMBL2243 O00519 Anandamide amidohydrolase 81.59% 97.53%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.11% 97.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.55% 92.62%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 80.16% 92.32%

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 fruticescens

Cross-Links

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PubChem 102119828
LOTUS LTS0230310
wikiData Q104993123