Euphroside

Details

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Internal ID 1ce6e89d-6a3e-4250-8a72-954e39df050d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aR,7S,7aR)-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carbaldehyde
SMILES (Canonical) CC1(CCC2(C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric) C[C@@]1(CC[C@]2([C@@H]1[C@@H](OC=C2C=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChI InChI=1S/C16H24O10/c1-15(22)2-3-16(23)7(4-17)6-24-14(12(15)16)26-13-11(21)10(20)9(19)8(5-18)25-13/h4,6,8-14,18-23H,2-3,5H2,1H3/t8-,9-,10+,11-,12-,13+,14+,15+,16+/m1/s1
InChI Key HDUJICSWDUDSBC-PGELYSMJSA-N
Popularity 17 references in papers

Physical and Chemical Properties

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Molecular Formula C16H24O10
Molecular Weight 376.36 g/mol
Exact Mass 376.13694696 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP -2.60
Atomic LogP (AlogP) -2.87
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

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76994-07-5
AKOS032962638
(1S,4aR,7S,7aR)-1-(-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a,7-dihydroxy-7-methylcyclopenta[c]pyran-4-carboxaldehyde

2D Structure

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2D Structure of Euphroside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7659 76.59%
Caco-2 - 0.8757 87.57%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8857 88.57%
Subcellular localzation Mitochondria 0.7195 71.95%
OATP2B1 inhibitior - 0.8603 86.03%
OATP1B1 inhibitior + 0.7909 79.09%
OATP1B3 inhibitior + 0.9184 91.84%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7879 78.79%
BSEP inhibitior - 0.8730 87.30%
P-glycoprotein inhibitior - 0.8623 86.23%
P-glycoprotein substrate - 0.8837 88.37%
CYP3A4 substrate + 0.6103 61.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8528 85.28%
CYP3A4 inhibition - 0.9341 93.41%
CYP2C9 inhibition - 0.8851 88.51%
CYP2C19 inhibition - 0.9071 90.71%
CYP2D6 inhibition - 0.9191 91.91%
CYP1A2 inhibition - 0.8644 86.44%
CYP2C8 inhibition - 0.7298 72.98%
CYP inhibitory promiscuity - 0.8847 88.47%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6368 63.68%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9780 97.80%
Skin irritation - 0.5643 56.43%
Skin corrosion - 0.9285 92.85%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5204 52.04%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.8217 82.17%
skin sensitisation - 0.8894 88.94%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.4523 45.23%
Acute Oral Toxicity (c) III 0.4596 45.96%
Estrogen receptor binding + 0.5913 59.13%
Androgen receptor binding - 0.4885 48.85%
Thyroid receptor binding + 0.5665 56.65%
Glucocorticoid receptor binding - 0.5279 52.79%
Aromatase binding + 0.6039 60.39%
PPAR gamma + 0.5539 55.39%
Honey bee toxicity - 0.8201 82.01%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6955 69.55%
Fish aquatic toxicity + 0.7290 72.90%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.68% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.60% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 95.13% 96.61%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.60% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.29% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.48% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.85% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.64% 86.33%
CHEMBL2581 P07339 Cathepsin D 85.22% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.83% 94.45%
CHEMBL220 P22303 Acetylcholinesterase 83.70% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.33% 89.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.03% 96.21%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.40% 100.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.24% 91.24%

Cross-Links

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PubChem 14589173
NPASS NPC260412
LOTUS LTS0110444
wikiData Q104388386