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

Details

• Internal ID: a236865f-48ae-43ba-b01d-74c08ab549d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,4aR,6aR,6bR,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxycarbonyl-2-hydroxy-6b-(hydroxymethyl)-4,6a,11,11,14b-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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(C(OC2OC(=O)C34CCC(CC3C5=CCC6C(C5(CC4)CO)(CCC7C6(CC(C(C7(C)C(=O)O)OC8C(C(C(C(O8)CO)O)O)O)O)C)C)(C)C)C)OC(=O)C)OC(=O)C)O)O)OC9C(C(C(CO9)OC1C(C(C(C(O1)CO)O)O)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]([C@H](O[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)CO)O)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)CO)C)OC(=O)C)OC(=O)C)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O)O
• InChI: InChI=1S/C63H98O31/c1-24-46(91-51-42(76)38(72)33(22-83-51)90-53-43(77)39(73)36(70)31(20-64)88-53)41(75)45(79)52(84-24)92-49-48(87-27(4)68)47(86-26(3)67)25(2)85-55(49)94-57(82)62-15-14-58(5,6)18-29(62)28-10-11-34-59(7)19-30(69)50(93-54-44(78)40(74)37(71)32(21-65)89-54)61(9,56(80)81)35(59)12-13-60(34,8)63(28,23-66)17-16-62/h10,24-25,29-55,64-66,69-79H,11-23H2,1-9H3,(H,80,81)/t24-,25+,29-,30-,31+,32+,33+,34+,35+,36-,37+,38-,39-,40-,41-,42+,43+,44+,45+,46-,47-,48-,49+,50-,51-,52-,53-,54-,55-,59+,60+,61-,62-,63-/m0/s1
• InChI Key: LSCYXLAZKRSAHE-WKPFCPMBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₃H₉₈O₃₁
• Molecular Weight: 1351.40 g/mol
• Exact Mass: 1350.6092063 g/mol
• Topological Polar Surface Area (TPSA): 483.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -3.37
• H-Bond Acceptor: 30
• H-Bond Donor: 15
• Rotatable Bonds: 16

Synonyms

• orb1680219
• AKOS040763540
• FS-8281

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8621	86.21%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7710	77.10%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9616	96.16%
P-glycoprotein inhibitior	+	0.7439	74.39%
P-glycoprotein substrate	+	0.6339	63.39%
CYP3A4 substrate	+	0.7378	73.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8804	88.04%
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	+	0.7550	75.50%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7542	75.42%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7959	79.59%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7224	72.24%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.6761	67.61%
Androgen receptor binding	+	0.7585	75.85%
Thyroid receptor binding	+	0.6776	67.76%
Glucocorticoid receptor binding	+	0.8084	80.84%
Aromatase binding	+	0.6827	68.27%
PPAR gamma	+	0.8152	81.52%
Honey bee toxicity	-	0.6386	63.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	99.59%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.08%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.44%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.54%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.25%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.86%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.24%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	89.26%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.14%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.08%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.82%	91.19%
CHEMBL5028	O14672	ADAM10	85.64%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.38%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.19%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.44%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.82%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.44%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.98%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.89%	86.92%

Plants that contains it

• Polygala fallax

Cross-Links

• PubChem: 102600403
• LOTUS: LTS0180257
• wikiData: Q105156469