Cussonoside A

Details

• Internal ID: 236d2b84-0ec9-4f1e-82d6-71325b77e704
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)O)C)(C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@@]45CC[C@@]6(C(=CC[C@H]7[C@]6(CC[C@@H]8[C@@]7(CC[C@@H]([C@@]8(C)CO)O)C)C)[C@@H]4CC(CC5)(C)C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C48H78O18/c1-22-30(52)32(54)35(57)40(62-22)65-38-25(19-49)63-39(37(59)34(38)56)61-20-26-31(53)33(55)36(58)41(64-26)66-42(60)48-16-14-43(2,3)18-24(48)23-8-9-28-44(4)12-11-29(51)45(5,21-50)27(44)10-13-47(28,7)46(23,6)15-17-48/h8,22,24-41,49-59H,9-21H2,1-7H3/t22-,24-,25+,26+,27+,28+,29-,30-,31+,32+,33-,34+,35+,36+,37+,38+,39+,40-,41-,44-,45-,46+,47+,48-/m0/s1
• InChI Key: YGSBJLPWANWGED-HYXYOFMCSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₈
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.14
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 57539-70-5
• CHEMBL540943
• Kizuta Cirensenoside O Saponin K3
• [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• Pulsatiloside C
• Hederagenin 28-O-(rhamnopyranosyl(1-4)glucopyranosyl(1-6))glucopyranosyl ester
• HN saponin H
• DTXSID801346774
• BDBM50322752
• 3beta,23-dihydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1->4)-O-beta-D-glucopyranosy1-(1->6)-beta-D-glucopyranosy1 ester
• Olean-12-en-28-oic acid, 3,23-dihydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranosyl ester, (3beta,4alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8896	88.96%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9133	91.33%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8336	83.36%
P-glycoprotein inhibitior	+	0.7419	74.19%
P-glycoprotein substrate	-	0.6113	61.13%
CYP3A4 substrate	+	0.7236	72.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6836	68.36%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9065	90.65%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7495	74.95%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8417	84.17%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8202	82.02%
Androgen receptor binding	+	0.7361	73.61%
Thyroid receptor binding	-	0.5276	52.76%
Glucocorticoid receptor binding	+	0.7061	70.61%
Aromatase binding	+	0.6566	65.66%
PPAR gamma	+	0.8095	80.95%
Honey bee toxicity	-	0.6773	67.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.34%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.40%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.68%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.71%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.44%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.39%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.29%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.54%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.11%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.95%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.32%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.62%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.74%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	82.18%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	81.42%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.41%	94.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.38%	96.90%
CHEMBL2581	P07339	Cathepsin D	80.03%	98.95%

Plants that contains it

• Anemonastrum tetrasepalum
• Caulophyllum thalictroides
• Clematis chinensis
• Clematis tibetana
• Cussonia arborea
• Eleutherococcus japonicus
• Eleutherococcus sieboldianus
• Hedera nepalensis
• Kalopanax septemlobus
• Pulsatilla campanella
• Stauntonia chinensis

Cross-Links

• PubChem: 171596
• NPASS: NPC102439
• LOTUS: LTS0199325
• wikiData: Q105348245