Protodioscin

Details

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Internal ID b4c43ceb-b78c-46ef-ad27-e01851c2c8f0
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
IUPAC Name (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)C)O)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC1(CCC(C)COC9C(C(C(C(O9)CO)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
InChI InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,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-/m1/s1
InChI Key LVTJOONKWUXEFR-UEZXSUPNSA-N
Popularity 85 references in papers

Physical and Chemical Properties

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Molecular Formula C51H84O22
Molecular Weight 1049.20 g/mol
Exact Mass 1048.54542430 g/mol
Topological Polar Surface Area (TPSA) 346.00 Ų
XlogP -1.30
Atomic LogP (AlogP) -1.98
H-Bond Acceptor 22
H-Bond Donor 13
Rotatable Bonds 14

Synonyms

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55056-80-9
Furostanol I
UNII-D0LC3PH24P
D0LC3PH24P
PROTODIOSCINE
CHEBI:8588
Furostane base-2H + O-Hex, O-Hex-dHex-dHex
Furost-5-ene-3,22,26-triol 3-chacotrioside-26-glucopyranoside
MFCD03427682
26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Protodioscin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7571 75.71%
Caco-2 - 0.8886 88.86%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7376 73.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8794 87.94%
OATP1B3 inhibitior + 0.8994 89.94%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.8354 83.54%
P-glycoprotein inhibitior + 0.7412 74.12%
P-glycoprotein substrate + 0.6579 65.79%
CYP3A4 substrate + 0.7497 74.97%
CYP2C9 substrate - 0.8020 80.20%
CYP2D6 substrate - 0.8336 83.36%
CYP3A4 inhibition - 0.9268 92.68%
CYP2C9 inhibition - 0.9182 91.82%
CYP2C19 inhibition - 0.9234 92.34%
CYP2D6 inhibition - 0.9343 93.43%
CYP1A2 inhibition - 0.9102 91.02%
CYP2C8 inhibition + 0.7231 72.31%
CYP inhibitory promiscuity - 0.9302 93.02%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5116 51.16%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.9046 90.46%
Skin irritation + 0.4929 49.29%
Skin corrosion - 0.9426 94.26%
Ames mutagenesis - 0.9300 93.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8226 82.26%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.8750 87.50%
skin sensitisation - 0.9214 92.14%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.9060 90.60%
Acute Oral Toxicity (c) I 0.5904 59.04%
Estrogen receptor binding + 0.8602 86.02%
Androgen receptor binding + 0.6992 69.92%
Thyroid receptor binding + 0.5595 55.95%
Glucocorticoid receptor binding + 0.7053 70.53%
Aromatase binding + 0.6974 69.74%
PPAR gamma + 0.7982 79.82%
Honey bee toxicity - 0.5984 59.84%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9176 91.76%

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 98.74% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.63% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 98.10% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.46% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.63% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.67% 95.89%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 91.44% 89.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.41% 89.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 91.26% 93.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.85% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.37% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.29% 95.89%
CHEMBL2581 P07339 Cathepsin D 89.25% 98.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.34% 96.61%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 87.91% 92.86%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.48% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 85.79% 94.75%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 85.34% 97.29%
CHEMBL2094135 Q96BI3 Gamma-secretase 84.90% 98.05%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 84.58% 98.46%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.16% 94.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.86% 100.00%
CHEMBL242 Q92731 Estrogen receptor beta 82.10% 98.35%
CHEMBL2996 Q05655 Protein kinase C delta 81.98% 97.79%
CHEMBL1914 P06276 Butyrylcholinesterase 81.92% 95.00%
CHEMBL2360 P00492 Hypoxanthine-guanine phosphoribosyltransferase 81.91% 87.38%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.78% 100.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 81.48% 91.71%
CHEMBL3401 O75469 Pregnane X receptor 80.93% 94.73%
CHEMBL4581 P52732 Kinesin-like protein 1 80.77% 93.18%
CHEMBL5255 O00206 Toll-like receptor 4 80.27% 92.50%

Cross-Links

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PubChem 441891
NPASS NPC39591
LOTUS LTS0262288
wikiData Q7251968