methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate

Details

• Internal ID: f367870b-a9e2-4145-b097-0f7a6d029eaf
• 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,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)OC)O)OC7C(C(C(C(O7)CO)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)OC)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)O
• InChI: InChI=1S/C49H78O19/c1-44(2)15-17-49(43(61)68-41-34(57)32(55)30(53)25(21-51)64-41)18-16-47(6)22(23(49)19-44)9-10-27-46(5)13-12-28(45(3,4)26(46)11-14-48(27,47)7)65-42-36(59)37(35(58)38(67-42)39(60)62-8)66-40-33(56)31(54)29(52)24(20-50)63-40/h9,23-38,40-42,50-59H,10-21H2,1-8H3/t23-,24+,25+,26-,27+,28-,29-,30+,31-,32-,33+,34+,35-,36+,37-,38-,40-,41-,42+,46-,47+,48+,49-/m0/s1
• InChI Key: FBNHNCMZFHURCE-IGKQOAJFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₈O₁₉
• Molecular Weight: 971.10 g/mol
• Exact Mass: 970.51373025 g/mol
• Topological Polar Surface Area (TPSA): 301.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• Tarasaponin III methyl ester
• CHEMBL449026
• DTXSID101103591
• beta-D-Glucopyranosiduronic acid, (3beta)-28-(beta-D-glucopyranosyloxy)-28-oxoolean-12-en-3-yl 3-O-beta-D-galactopyranosyl-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7095	70.95%
Caco-2	-	0.8835	88.35%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7291	72.91%
OATP1B3 inhibitior	-	0.3603	36.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8593	85.93%
P-glycoprotein inhibitior	+	0.7559	75.59%
P-glycoprotein substrate	-	0.7809	78.09%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8735	87.35%
CYP3A4 inhibition	-	0.9142	91.42%
CYP2C9 inhibition	-	0.8703	87.03%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9480	94.80%
CYP1A2 inhibition	-	0.8810	88.10%
CYP2C8 inhibition	+	0.7095	70.95%
CYP inhibitory promiscuity	-	0.9614	96.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.6660	66.60%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7217	72.17%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9447	94.47%
skin sensitisation	-	0.8977	89.77%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7708	77.08%
Acute Oral Toxicity (c)	III	0.7305	73.05%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.7408	74.08%
Thyroid receptor binding	-	0.5284	52.84%
Glucocorticoid receptor binding	+	0.7804	78.04%
Aromatase binding	+	0.6219	62.19%
PPAR gamma	+	0.8042	80.42%
Honey bee toxicity	-	0.6623	66.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9479	94.79%

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	98.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.48%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.22%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.51%	94.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.77%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.01%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.27%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.65%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.14%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.44%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.20%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.16%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.21%	95.89%

Plants that contains it

• Calendula officinalis

Cross-Links

• PubChem: 44566501
• NPASS: NPC223301
• LOTUS: LTS0265701
• wikiData: Q104992744