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

Details

• Internal ID: 1a3dcbdd-0c77-4747-821c-3b08e8ff9c46
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxycarbonyl-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-3-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxycarbonyloxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC(=O)C34CCC(CC3C5=CCC6C(C5(CC4)C)(CCC7C6(CC(C(C7(C)C(=O)O)OC8C(C(C(C(O8)C(=O)OC)O)O)O)O)C)C)(C)C)O)O)O)O)OC9C(C(C(CO9)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2OC(=O)[C@@]34CC[C@@]5(C(=CC[C@H]6[C@]5(CC[C@@H]7[C@@]6(C[C@@H]([C@@H]([C@@]7(C)C(=O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)OC)O)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)C)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O
• InChI: InChI=1S/C53H82O24/c1-21-37(73-42-34(62)29(57)25(55)19-70-42)33(61)36(64)43(72-21)75-39-30(58)26(56)20-71-45(39)77-47(68)53-15-13-48(2,3)17-23(53)22-9-10-27-49(4)18-24(54)40(76-44-35(63)31(59)32(60)38(74-44)41(65)69-8)52(7,46(66)67)28(49)11-12-51(27,6)50(22,5)14-16-53/h9,21,23-40,42-45,54-64H,10-20H2,1-8H3,(H,66,67)/t21-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34+,35+,36+,37-,38-,39+,40-,42-,43-,44-,45-,49+,50+,51+,52-,53-/m0/s1
• InChI Key: NLYNGEGTELKAET-XYLJBLAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₂O₂₄
• Molecular Weight: 1103.20 g/mol
• Exact Mass: 1102.51960348 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.51
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8158	81.58%
Caco-2	-	0.8730	87.30%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8431	84.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7938	79.38%
OATP1B3 inhibitior	+	0.8431	84.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9247	92.47%
P-glycoprotein inhibitior	+	0.7467	74.67%
P-glycoprotein substrate	+	0.5996	59.96%
CYP3A4 substrate	+	0.7341	73.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.9164	91.64%
CYP2C9 inhibition	-	0.8803	88.03%
CYP2C19 inhibition	-	0.9085	90.85%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.8966	89.66%
CYP2C8 inhibition	+	0.7730	77.30%
CYP inhibitory promiscuity	-	0.9852	98.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5690	56.90%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.6320	63.20%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7402	74.02%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6327	63.27%
Acute Oral Toxicity (c)	III	0.6080	60.80%
Estrogen receptor binding	+	0.7715	77.15%
Androgen receptor binding	+	0.7504	75.04%
Thyroid receptor binding	+	0.6141	61.41%
Glucocorticoid receptor binding	+	0.7923	79.23%
Aromatase binding	+	0.6319	63.19%
PPAR gamma	+	0.8304	83.04%
Honey bee toxicity	-	0.6678	66.78%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9540	95.40%

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	99.34%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.03%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.36%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.24%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.40%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.21%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.11%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	88.87%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	86.95%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.63%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.60%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.18%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.16%	91.07%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	83.85%	87.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.72%	97.09%
CHEMBL5028	O14672	ADAM10	83.04%	97.50%
CHEMBL2581	P07339	Cathepsin D	80.33%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.23%	92.62%
CHEMBL4302	P08183	P-glycoprotein 1	80.21%	92.98%

Plants that contains it

• Medicago sativa

Cross-Links

• PubChem: 162881906
• LOTUS: LTS0001391
• wikiData: Q105181631