Frugoside

Details

• Internal ID: e0fc7f04-bddb-4ce9-accd-42a0c8e5254e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-10-(hydroxymethyl)-13-methyl-3-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@H](C(O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)CO)O)O)O
• InChI: InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17-,18+,19-,20+,21-,23-,24-,25-,26?,27-,28-,29+/m1/s1
• InChI Key: WPVGSIBYLZQSIK-VEZJFPMXSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.70 g/mol
• Exact Mass: 536.29853298 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.90

Synonyms

• 546-02-1
• 3-[(3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-10-(hydroxymethyl)-13-methyl-3-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• Cannogenol-3-O-beta-D-allomethyloside
• Frugosid [German]
• Frugosid
• Coroglaucigenin-D-allomethylosid [German]
• Coroglaucigenin-D-allomethylosid
• DTXSID70276235
• Card-20(22)-enolide, 3-((6-deoxy-D-allopyranosyl)oxy)-14,19-dihydroxy-, (3-beta,5-alpha)-
• Card-20(22)-enolide, 3-((6-deoxy-D-allopyranosyl)oxy)-14,19-dihydroxy-, (3beta,5alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

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	98.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.61%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.64%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.17%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.41%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.30%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.61%	82.69%
CHEMBL2581	P07339	Cathepsin D	87.90%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.87%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.65%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.60%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.04%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.99%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.24%	89.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.16%	90.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.32%	92.94%
CHEMBL4208	P20618	Proteasome component C5	82.50%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.96%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.34%	98.46%

Plants that contains it

• Asclepias curassavica
• Asclepias incarnata
• Asclepias tuberosa
• Calotropis gigantea
• Calotropis procera
• Gomphocarpus fruticosus subsp. fruticosus
• Gomphocarpus sinaicus

Cross-Links

• PubChem: 120728
• LOTUS: LTS0078621
• wikiData: Q82006646