methyl (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]-3,4,5-trihydroxyoxane-2-carboxylate

Details

• Internal ID: f8c22ee2-5f9a-4add-9db3-803fec52d9cd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (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]-3,4,5-trihydroxyoxane-2-carboxylate
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)OC)O)O)O)C)C(=O)OC7C(C(C(CO7)O)OC8C(C(C(C(O8)CO)O)O)O)OC(=O)C=CC9=CC=C(C=C9)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)OC)O)O)O
• InChI: InChI=1S/C57H82O21/c1-52(2)21-22-57(51(70)78-50-46(75-37(62)16-11-27-9-12-28(59)13-10-27)44(31(60)26-72-50)76-48-42(67)39(64)38(63)32(25-58)73-48)30(23-52)29-14-15-34-54(5)19-18-36(74-49-43(68)40(65)41(66)45(77-49)47(69)71-8)53(3,4)33(54)17-20-55(34,6)56(29,7)24-35(57)61/h9-14,16,30-36,38-46,48-50,58-61,63-68H,15,17-26H2,1-8H3/b16-11+/t30-,31+,32+,33-,34+,35+,36-,38+,39-,40-,41-,42+,43+,44-,45-,46+,48-,49+,50-,54-,55+,56+,57+/m0/s1
• InChI Key: OEXIAAITFXCTKI-UNGNKPJMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₈₂O₂₁
• Molecular Weight: 1103.20 g/mol
• Exact Mass: 1102.53485962 g/mol
• Topological Polar Surface Area (TPSA): 327.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 21
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8498	84.98%
Caco-2	-	0.8659	86.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7899	78.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3277	32.77%
OATP1B3 inhibitior	-	0.2743	27.43%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9644	96.44%
P-glycoprotein inhibitior	+	0.7464	74.64%
P-glycoprotein substrate	+	0.6145	61.45%
CYP3A4 substrate	+	0.7548	75.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8718	87.18%
CYP3A4 inhibition	-	0.7267	72.67%
CYP2C9 inhibition	-	0.8290	82.90%
CYP2C19 inhibition	-	0.8146	81.46%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.7939	79.39%
CYP2C8 inhibition	+	0.8508	85.08%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5897	58.97%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8987	89.87%
Skin irritation	-	0.6958	69.58%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7622	76.22%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8854	88.54%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8285	82.85%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.7559	75.59%
Androgen receptor binding	+	0.7533	75.33%
Thyroid receptor binding	+	0.6573	65.73%
Glucocorticoid receptor binding	+	0.8018	80.18%
Aromatase binding	+	0.5717	57.17%
PPAR gamma	+	0.8160	81.60%
Honey bee toxicity	-	0.6142	61.42%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9767	97.67%

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	99.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.05%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.07%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	94.49%	89.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.46%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.49%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.05%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.58%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.39%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.29%	99.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.12%	89.44%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.83%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.23%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.42%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.29%	98.95%
CHEMBL206	P03372	Estrogen receptor alpha	83.08%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.88%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.77%	95.89%
CHEMBL5028	O14672	ADAM10	81.08%	97.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.71%	89.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.39%	91.07%

Plants that contains it

• Tragopogon porrifolius

Cross-Links

• PubChem: 21626565
• LOTUS: LTS0028518
• wikiData: Q105190643