Euphroside

Details

• 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

• 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

• 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

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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%

Plants that contains it

• Euphrasia nemorosa
• Euphrasia salisburgensis
• Orthocarpus tolmiei
• Pedicularis groenlandica
• Pedicularis kansuensis
• Pedicularis muscicola
• Pedicularis nordmanniana
• Pedicularis palustris
• Pedicularis rex
• Pedicularis semitorta
• Pedicularis verticillata
• Penstemon procerus
• Penstemon rydbergii
• Rotheca incisa
• Rotheca serrata
• Titanotrichum oldhamii

Cross-Links

• PubChem: 14589173
• NPASS: NPC260412
• LOTUS: LTS0110444
• wikiData: Q104388386