(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8-hydroxy-8a-[(2S,3R,4S,5R)-5-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-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]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: b7aa9faf-05d7-4558-bce2-44c427382b25
• 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,8R,8aR,12aS,14aR,14bR)-8-hydroxy-8a-[(2S,3R,4S,5R)-5-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-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]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C(=O)OC8C(C(C(CO8)O)OC9C(C(C(C(O9)CO)O)O)O)OC(=O)C=CC1=CC=C(C=C1)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=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](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)OC(=O)/C=C/C8=CC=C(C=C8)O)O)C)C)(C)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)C(=O)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C62H90O26/c1-57(2)20-21-62(56(79)88-54-50(84-38(68)15-10-27-8-11-28(65)12-9-27)47(31(66)26-80-54)85-52-45(75)41(71)39(69)32(24-63)81-52)30(22-57)29-13-14-35-59(5)18-17-37(58(3,4)34(59)16-19-60(35,6)61(29,7)23-36(62)67)83-55-49(44(74)43(73)48(86-55)51(77)78)87-53-46(76)42(72)40(70)33(25-64)82-53/h8-13,15,30-37,39-50,52-55,63-67,69-76H,14,16-26H2,1-7H3,(H,77,78)/b15-10+/t30-,31+,32+,33+,34-,35+,36+,37-,39+,40-,41-,42-,43-,44-,45+,46+,47-,48-,49+,50+,52-,53-,54-,55+,59-,60+,61+,62+/m0/s1
• InChI Key: WPUFCIRZLQTGLH-VZMBNZODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₂H₉₀O₂₆
• Molecular Weight: 1251.40 g/mol
• Exact Mass: 1250.57203297 g/mol
• Topological Polar Surface Area (TPSA): 418.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): -0.36
• H-Bond Acceptor: 25
• H-Bond Donor: 14
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8567	85.67%
Caco-2	-	0.8637	86.37%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8317	83.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3446	34.46%
OATP1B3 inhibitior	-	0.4152	41.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9532	95.32%
P-glycoprotein inhibitior	+	0.7438	74.38%
P-glycoprotein substrate	+	0.5569	55.69%
CYP3A4 substrate	+	0.7500	75.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.7238	72.38%
CYP2C9 inhibition	-	0.8199	81.99%
CYP2C19 inhibition	-	0.8379	83.79%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.7832	78.32%
CYP2C8 inhibition	+	0.8553	85.53%
CYP inhibitory promiscuity	-	0.9494	94.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5954	59.54%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8970	89.70%
Skin irritation	-	0.6597	65.97%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7591	75.91%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9228	92.28%
Acute Oral Toxicity (c)	III	0.6582	65.82%
Estrogen receptor binding	+	0.6869	68.69%
Androgen receptor binding	+	0.7546	75.46%
Thyroid receptor binding	+	0.6877	68.77%
Glucocorticoid receptor binding	+	0.8088	80.88%
Aromatase binding	+	0.6693	66.93%
PPAR gamma	+	0.8148	81.48%
Honey bee toxicity	-	0.6352	63.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9878	98.78%

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	98.82%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.42%	86.33%
CHEMBL206	P03372	Estrogen receptor alpha	94.97%	97.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.76%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.64%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.32%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.24%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.83%	94.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.77%	89.67%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.80%	89.44%
CHEMBL2581	P07339	Cathepsin D	86.53%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.84%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	84.78%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.36%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.50%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.95%	92.50%
CHEMBL5028	O14672	ADAM10	81.43%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.06%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.81%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.74%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.63%	91.71%

Plants that contains it

• Tragopogon pratensis

Cross-Links

• PubChem: 101630875
• LOTUS: LTS0191456
• wikiData: Q105310193