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

Details

• Internal ID: eb38781a-481b-4973-8f72-9fcc0aeae135
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(CCC8(C7CC(CC8O)(C)C)C)C)C)C)C(=O)O)O)O)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]2O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H](C4(C)C)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7CC(C[C@H]8O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C48H78O17/c1-21-29(51)31(53)35(57)40(60-21)64-37-32(54)30(52)24(20-49)61-41(37)65-38-34(56)33(55)36(39(58)59)63-42(38)62-28-13-14-46(7)25(44(28,4)5)12-15-48(9)26(46)11-10-22-23-18-43(2,3)19-27(50)45(23,6)16-17-47(22,48)8/h10,21,23-38,40-42,49-57H,11-20H2,1-9H3,(H,58,59)/t21-,23-,24+,25-,26+,27+,28-,29-,30-,31+,32-,33-,34-,35+,36-,37+,38+,40-,41-,42+,45+,46-,47+,48+/m0/s1
• InChI Key: ISTWCKNDZOSMPU-UUOPLRLOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₇
• Molecular Weight: 927.10 g/mol
• Exact Mass: 926.52390102 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8519	85.19%
Caco-2	-	0.9283	92.83%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8632	86.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7555	75.55%
OATP1B3 inhibitior	-	0.5253	52.53%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7418	74.18%
P-glycoprotein inhibitior	+	0.7545	75.45%
P-glycoprotein substrate	-	0.7793	77.93%
CYP3A4 substrate	+	0.7138	71.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.8812	88.12%
CYP2C9 inhibition	-	0.8589	85.89%
CYP2C19 inhibition	-	0.9177	91.77%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	-	0.8706	87.06%
CYP2C8 inhibition	+	0.7255	72.55%
CYP inhibitory promiscuity	-	0.9515	95.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.5441	54.41%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7368	73.68%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.9447	94.47%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.9341	93.41%
Acute Oral Toxicity (c)	III	0.7787	77.87%
Estrogen receptor binding	+	0.8045	80.45%
Androgen receptor binding	+	0.7259	72.59%
Thyroid receptor binding	-	0.6092	60.92%
Glucocorticoid receptor binding	+	0.6892	68.92%
Aromatase binding	+	0.6723	67.23%
PPAR gamma	+	0.7959	79.59%
Honey bee toxicity	-	0.7062	70.62%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9532	95.32%

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	96.90%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.35%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.41%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.01%	93.00%
CHEMBL2581	P07339	Cathepsin D	89.46%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.44%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.30%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.75%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.42%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.93%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.49%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.46%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.43%	95.89%
CHEMBL5028	O14672	ADAM10	81.56%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.77%	100.00%

Plants that contains it

• Abrus precatorius
• Astragalus condensatus
• Baptisia australis
• Bertya dimerostigma
• Canavalia gladiata
• Crotalaria albida
• Dalbergia hupeana
• Delphinium barbeyi
• Pueraria montana var. lobata
• Sophora tonkinensis
• Styphnolobium japonicum

Cross-Links

• PubChem: 21629874
• NPASS: NPC177109
• LOTUS: LTS0131682
• wikiData: Q104399647