(2S,4S)-6-[[(4aR,6bS,8R,9R,14aR)-8,9,10-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 8f0b3753-190d-4fc2-a6b9-cc63377f251c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,4S)-6-[[(4aR,6bS,8R,9R,14aR)-8,9,10-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(OC(C3OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CC=C8C7(CC(C9(C8CC(C(C9O)O)(C)C)CO)O)C)C)C)C(=O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1C([C@H]([C@H]([C@@H](O1)OC2[C@H]([C@H]([C@H](OC2O[C@H]3C([C@H](OC(C3OC4C([C@H](C([C@H](O4)CO)O)O)O)OC5CCC6([C@H](C5(C)C)CCC7([C@@H]6CC=C8[C@]7(C[C@H](C9(C8CC(C([C@@H]9O)O)(C)C)CO)O)C)C)C)C(=O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C54H88O25/c1-20-29(59)32(62)35(65)45(72-20)78-40-34(64)31(61)24(18-56)74-47(40)76-38-37(67)39(44(70)71)77-48(41(38)79-46-36(66)33(63)30(60)23(17-55)73-46)75-28-12-13-51(6)25(50(28,4)5)11-14-52(7)26(51)10-9-21-22-15-49(2,3)42(68)43(69)54(22,19-57)27(58)16-53(21,52)8/h9,20,22-43,45-48,55-69H,10-19H2,1-8H3,(H,70,71)/t20-,22?,23+,24+,25-,26+,27+,28?,29?,30?,31-,32+,33-,34-,35+,36?,37?,38-,39-,40?,41?,42?,43-,45-,46?,47?,48?,51?,52?,53+,54?/m0/s1
• InChI Key: RYALPQKRBGXULF-HQNDSBKBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₅
• Molecular Weight: 1137.30 g/mol
• Exact Mass: 1136.56146829 g/mol
• Topological Polar Surface Area (TPSA): 415.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -3.53
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8926	89.26%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7609	76.09%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8743	87.43%
P-glycoprotein inhibitior	+	0.7479	74.79%
P-glycoprotein substrate	-	0.6490	64.90%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
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	+	0.7477	74.77%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.8524	85.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7403	74.03%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9098	90.98%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8905	89.05%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8028	80.28%
Androgen receptor binding	+	0.7491	74.91%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7534	75.34%
Aromatase binding	+	0.6328	63.28%
PPAR gamma	+	0.8156	81.56%
Honey bee toxicity	-	0.6787	67.87%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
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	96.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.98%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.64%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.41%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.96%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.32%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.72%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.22%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	85.77%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.09%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.39%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.58%	89.00%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.23%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.09%	91.07%

Plants that contains it

• Eupatorium semiserratum

Cross-Links

• PubChem: 6325062
• NPASS: NPC238512