[(3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4S)-4-methyl-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoate

Details

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Internal ID d2cb878d-4f1a-467a-b85e-1840a259ea28
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name [(3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4S)-4-methyl-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoate
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3CCC4(C(C3)CCC5C4CCC6(C5CC(C6OC(=O)C)OC(=O)CCC(C)COC7C(C(C(C(O7)CO)O)O)O)C)C)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)O[C@H]3CC[C@]4([C@H](C3)CC[C@@H]5[C@@H]4CC[C@]6([C@H]5C[C@@H]([C@@H]6OC(=O)C)OC(=O)CC[C@H](C)CO[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)C)C)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O)O)O)O
InChI InChI=1S/C51H84O24/c1-20(18-66-47-42(64)39(61)35(57)30(17-52)73-47)7-10-32(54)72-29-16-28-26-9-8-24-15-25(11-13-50(24,5)27(26)12-14-51(28,6)45(29)70-23(4)53)71-49-44(75-48-43(65)38(60)34(56)22(3)69-48)40(62)36(58)31(74-49)19-67-46-41(63)37(59)33(55)21(2)68-46/h20-22,24-31,33-49,52,55-65H,7-19H2,1-6H3/t20-,21-,22-,24-,25-,26+,27-,28-,29-,30+,31+,33-,34-,35-,36-,37+,38+,39-,40-,41+,42+,43+,44+,45-,46+,47+,48-,49-,50-,51-/m0/s1
InChI Key ZVTVUCKSSQCBMP-JHNDGZJMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C51H84O24
Molecular Weight 1081.20 g/mol
Exact Mass 1080.53525354 g/mol
Topological Polar Surface Area (TPSA) 369.00 Ų
XlogP -1.20
Atomic LogP (AlogP) -2.40
H-Bond Acceptor 24
H-Bond Donor 12
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4S)-4-methyl-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6233 62.33%
Caco-2 - 0.8776 87.76%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8012 80.12%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8455 84.55%
OATP1B3 inhibitior + 0.9202 92.02%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.5250 52.50%
BSEP inhibitior + 0.7996 79.96%
P-glycoprotein inhibitior + 0.7443 74.43%
P-glycoprotein substrate + 0.6028 60.28%
CYP3A4 substrate + 0.7488 74.88%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8804 88.04%
CYP3A4 inhibition - 0.9339 93.39%
CYP2C9 inhibition - 0.9276 92.76%
CYP2C19 inhibition - 0.9100 91.00%
CYP2D6 inhibition - 0.9686 96.86%
CYP1A2 inhibition - 0.9134 91.34%
CYP2C8 inhibition + 0.6266 62.66%
CYP inhibitory promiscuity - 0.9707 97.07%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6946 69.46%
Eye corrosion - 0.9915 99.15%
Eye irritation - 0.9028 90.28%
Skin irritation - 0.6863 68.63%
Skin corrosion - 0.9490 94.90%
Ames mutagenesis - 0.7515 75.15%
Human Ether-a-go-go-Related Gene inhibition + 0.7794 77.94%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.9573 95.73%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.8174 81.74%
Acute Oral Toxicity (c) I 0.5493 54.93%
Estrogen receptor binding + 0.8453 84.53%
Androgen receptor binding + 0.6836 68.36%
Thyroid receptor binding + 0.5594 55.94%
Glucocorticoid receptor binding + 0.7523 75.23%
Aromatase binding + 0.6763 67.63%
PPAR gamma + 0.7936 79.36%
Honey bee toxicity - 0.6046 60.46%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5555 55.55%
Fish aquatic toxicity + 0.8912 89.12%

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 98.87% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.65% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.12% 97.25%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 95.88% 96.21%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.41% 94.45%
CHEMBL237 P41145 Kappa opioid receptor 95.36% 98.10%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 93.57% 95.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.04% 97.09%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 92.25% 89.05%
CHEMBL5255 O00206 Toll-like receptor 4 91.69% 92.50%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 91.65% 96.47%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.94% 96.38%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 90.39% 95.36%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.95% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.88% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 89.40% 90.17%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 88.82% 82.50%
CHEMBL340 P08684 Cytochrome P450 3A4 88.74% 91.19%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 86.87% 97.86%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.50% 96.77%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 85.91% 97.50%
CHEMBL4302 P08183 P-glycoprotein 1 85.56% 92.98%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 85.47% 95.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.45% 100.00%
CHEMBL2581 P07339 Cathepsin D 84.88% 98.95%
CHEMBL2007625 O75874 Isocitrate dehydrogenase [NADP] cytoplasmic 84.70% 99.00%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 84.67% 98.46%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.07% 94.33%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.71% 98.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.41% 96.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.92% 89.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.60% 93.56%
CHEMBL4581 P52732 Kinesin-like protein 1 82.40% 93.18%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 82.33% 95.58%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.25% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.24% 99.17%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.21% 91.24%
CHEMBL2094135 Q96BI3 Gamma-secretase 82.15% 98.05%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.89% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.72% 97.36%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.11% 96.90%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.98% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.35% 95.89%
CHEMBL5028 O14672 ADAM10 80.34% 97.50%

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.
Linum usitatissimum
Smilax riparia

Cross-Links

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PubChem 162821217
LOTUS LTS0024880
wikiData Q104984593