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[(1S,2S,3'S,4S,4'S,6S,7R,8R,9S,12S,13R,14R,16R)-14-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6S)-5-acetyloxy-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3',16-dihydroxy-9,13-dimethyl-5'-methylidene-4'-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-7-yl]methyl acetate

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 722d38d9-ab9b-4f6e-b5c5-39c245d41b98
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
IUPAC Name [(1S,2S,3'S,4S,4'S,6S,7R,8R,9S,12S,13R,14R,16R)-14-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6S)-5-acetyloxy-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3',16-dihydroxy-9,13-dimethyl-5'-methylidene-4'-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-7-yl]methyl acetate
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C3(C(C4C(O3)CC5C4(CCC6C5CC=C7C6(C(CC(C7)O)OC8C(C(C(CO8)O)OC9C(C(C(CO9)O)O)O)OC1C(C(C(C(O1)C)OC(=O)C)OC1C(C(CO1)(CO)O)O)O)C)C)COC(=O)C)OCC2=C)O)O)O)O
SMILES (Isomeric) C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@@H]([C@@]3([C@H]([C@H]4[C@@H](O3)C[C@@H]5[C@@]4(CC[C@H]6[C@H]5CC=C7[C@@]6([C@@H](C[C@@H](C7)O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)OC(=O)C)O[C@H]1[C@@H]([C@](CO1)(CO)O)O)O)C)C)COC(=O)C)OCC2=C)O)O)O)O
InChI InChI=1S/C58H88O29/c1-21-15-78-58(48(71)43(21)83-51-41(69)39(67)37(65)22(2)79-51)31(16-74-24(4)60)36-34(87-58)14-30-28-9-8-26-12-27(62)13-35(56(26,7)29(28)10-11-55(30,36)6)82-53-47(45(33(64)18-76-53)84-50-40(68)38(66)32(63)17-75-50)86-52-42(70)46(44(23(3)80-52)81-25(5)61)85-54-49(72)57(73,19-59)20-77-54/h8,22-23,27-54,59,62-73H,1,9-20H2,2-7H3/t22-,23+,27-,28-,29+,30+,31+,32-,33+,34+,35-,36+,37-,38+,39+,40-,41-,42-,43+,44+,45+,46+,47-,48+,49+,50+,51+,52+,53+,54+,55+,56+,57-,58+/m1/s1
InChI Key GWKXWFUKJVEVIT-OCZWOLEMSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C58H88O29
Molecular Weight 1249.30 g/mol
Exact Mass 1248.54112677 g/mol
Topological Polar Surface Area (TPSA) 426.00 Ų
XlogP -4.60
Atomic LogP (AlogP) -4.24
H-Bond Acceptor 29
H-Bond Donor 13
Rotatable Bonds 14

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,3'S,4S,4'S,6S,7R,8R,9S,12S,13R,14R,16R)-14-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6S)-5-acetyloxy-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3',16-dihydroxy-9,13-dimethyl-5'-methylidene-4'-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-7-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7854 78.54%
Caco-2 - 0.8690 86.90%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8253 82.53%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8272 82.72%
OATP1B3 inhibitior + 0.8889 88.89%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6021 60.21%
BSEP inhibitior + 0.9412 94.12%
P-glycoprotein inhibitior + 0.7452 74.52%
P-glycoprotein substrate + 0.7891 78.91%
CYP3A4 substrate + 0.7682 76.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8822 88.22%
CYP3A4 inhibition - 0.7778 77.78%
CYP2C9 inhibition - 0.8920 89.20%
CYP2C19 inhibition - 0.9194 91.94%
CYP2D6 inhibition - 0.9448 94.48%
CYP1A2 inhibition - 0.9074 90.74%
CYP2C8 inhibition + 0.8348 83.48%
CYP inhibitory promiscuity - 0.9571 95.71%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5077 50.77%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.8989 89.89%
Skin irritation + 0.5844 58.44%
Skin corrosion - 0.9336 93.36%
Ames mutagenesis - 0.6764 67.64%
Human Ether-a-go-go-Related Gene inhibition + 0.7860 78.60%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.6070 60.70%
skin sensitisation - 0.9185 91.85%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.5175 51.75%
Acute Oral Toxicity (c) III 0.5208 52.08%
Estrogen receptor binding + 0.7780 77.80%
Androgen receptor binding + 0.7577 75.77%
Thyroid receptor binding + 0.6485 64.85%
Glucocorticoid receptor binding + 0.7972 79.72%
Aromatase binding + 0.6488 64.88%
PPAR gamma + 0.8248 82.48%
Honey bee toxicity - 0.5781 57.81%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.9787 97.87%

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
CHEMBL226 P30542 Adenosine A1 receptor 99.20% 95.93%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.61% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.67% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.37% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.34% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 95.15% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.96% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.11% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.06% 97.25%
CHEMBL2179 P04062 Beta-glucocerebrosidase 92.04% 85.31%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.64% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.30% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.03% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 88.64% 91.19%
CHEMBL5255 O00206 Toll-like receptor 4 88.59% 92.50%
CHEMBL2243 O00519 Anandamide amidohydrolase 87.73% 97.53%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.60% 96.77%
CHEMBL221 P23219 Cyclooxygenase-1 87.52% 90.17%
CHEMBL1871 P10275 Androgen Receptor 84.76% 96.43%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 84.75% 92.88%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.71% 82.69%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 84.37% 97.21%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.83% 96.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.70% 94.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.16% 92.94%
CHEMBL3401 O75469 Pregnane X receptor 83.15% 94.73%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.85% 91.24%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 82.76% 96.90%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.42% 99.23%
CHEMBL5028 O14672 ADAM10 82.00% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.86% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.47% 97.14%
CHEMBL2581 P07339 Cathepsin D 81.17% 98.95%

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.
Helleborus orientalis

Cross-Links

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PubChem 10975315
LOTUS LTS0262353
wikiData Q105022478