(3R,4R,6aS,6bR,8S,8aS,12aR,14bS)-8a-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxycarbonyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid

Details

• Internal ID: a413bb8f-64fc-427f-862d-6315cdd38398
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3R,4R,6aS,6bR,8S,8aS,12aR,14bS)-8a-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxycarbonyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C(=O)O)OC6C(C(C(CO6)O)O)O)C)C(=O)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@](C1CC[C@]3(C2CC=C4[C@@]3(C[C@@H]([C@]5([C@@H]4CC(CC5)(C)C)C(=O)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO[C@@H]7[C@H]([C@@H]([C@H]([C@@H](O7)CO)O)O)O)O)O[C@@H]8[C@H]([C@@H]([C@H]([C@@H](O8)CO)O)O)O)O)O)C)C)(C)C(=O)O)O[C@@H]9[C@H]([C@@H]([C@H](CO9)O)O)O
• InChI: InChI=1S/C53H84O25/c1-48(2)13-14-53(47(70)78-45-40(67)41(77-44-39(66)36(63)33(60)25(18-55)74-44)34(61)26(75-45)20-72-42-38(65)35(62)32(59)24(17-54)73-42)22(15-48)21-7-8-27-49(3)11-10-30(76-43-37(64)31(58)23(56)19-71-43)52(6,46(68)69)28(49)9-12-50(27,4)51(21,5)16-29(53)57/h7,22-45,54-67H,8-20H2,1-6H3,(H,68,69)/t22-,23+,24+,25+,26+,27?,28?,29+,30-,31-,32+,33+,34+,35-,36-,37+,38+,39+,40+,41-,42+,43-,44-,45-,49+,50+,51+,52-,53+/m1/s1
• InChI Key: GAEHQHKGPCGEPQ-HCVUUTBASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₄O₂₅
• Molecular Weight: 1121.20 g/mol
• Exact Mass: 1120.53016816 g/mol
• Topological Polar Surface Area (TPSA): 411.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -3.36
• H-Bond Acceptor: 24
• H-Bond Donor: 15
• Rotatable Bonds: 12

Synonyms

• 223376-72-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7251	72.51%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8933	89.33%
P-glycoprotein inhibitior	+	0.7467	74.67%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7333	73.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7449	74.49%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9007	90.07%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7462	74.62%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8299	82.99%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7923	79.23%
Androgen receptor binding	+	0.7442	74.42%
Thyroid receptor binding	+	0.5358	53.58%
Glucocorticoid receptor binding	+	0.7481	74.81%
Aromatase binding	+	0.6246	62.46%
PPAR gamma	+	0.8082	80.82%
Honey bee toxicity	-	0.6942	69.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9585	95.85%

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	98.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.21%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.35%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.12%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.46%	96.61%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.86%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.20%	95.56%
CHEMBL5028	O14672	ADAM10	85.10%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	84.77%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.33%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.86%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.77%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	83.52%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.98%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.82%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	82.60%	91.19%
CHEMBL1871	P10275	Androgen Receptor	82.58%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.25%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.13%	95.89%

Plants that contains it

• Saponaria officinalis

Cross-Links

• PubChem: 133562532
• LOTUS: LTS0153107
• wikiData: Q105005336