(2S,3S,4R)-2-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-acetyloxy-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid

Details

• Internal ID: 636daa3c-650f-425e-ba36-5576a4716692
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4R)-2-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-acetyloxy-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C=C(OC(C2OC(=O)C)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C)C)C)C(=O)O)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2C=C(O[C@@H]([C@H]2OC(=O)C)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C)C)C)C(=O)O)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C64H90O25/c1-30-47(78-32(3)66)50(81-35(6)69)52(83-37(8)71)56(77-30)85-41-27-42(54(73)74)86-55(49(41)80-34(5)68)88-46-20-21-61(14)44(60(46,12)13)19-22-63(16)45(61)18-17-39-40-28-59(10,11)23-25-64(40,26-24-62(39,63)15)58(75)89-57-53(84-38(9)72)51(82-36(7)70)48(79-33(4)67)43(87-57)29-76-31(2)65/h17,27,30,40-41,43-53,55-57H,18-26,28-29H2,1-16H3,(H,73,74)/t30-,40-,41+,43+,44-,45+,46-,47-,48+,49-,50+,51-,52+,53+,55+,56-,57-,61-,62+,63+,64-/m0/s1
• InChI Key: ZPMPQZXZDUVCPZ-NDQWPIQMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₄H₉₀O₂₅
• Molecular Weight: 1259.40 g/mol
• Exact Mass: 1258.57711835 g/mol
• Topological Polar Surface Area (TPSA): 320.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 6.98
• H-Bond Acceptor: 24
• H-Bond Donor: 1
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9693	96.93%
Caco-2	-	0.8552	85.52%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8825	88.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7005	70.05%
OATP1B3 inhibitior	-	0.2720	27.20%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9914	99.14%
P-glycoprotein inhibitior	+	0.7472	74.72%
P-glycoprotein substrate	-	0.5064	50.64%
CYP3A4 substrate	+	0.7340	73.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8925	89.25%
CYP3A4 inhibition	-	0.8194	81.94%
CYP2C9 inhibition	-	0.8669	86.69%
CYP2C19 inhibition	-	0.9515	95.15%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.8277	82.77%
CYP2C8 inhibition	+	0.7589	75.89%
CYP inhibitory promiscuity	-	0.9380	93.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5961	59.61%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8967	89.67%
Skin irritation	-	0.5479	54.79%
Skin corrosion	-	0.9481	94.81%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7304	73.04%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8416	84.16%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8793	87.93%
Acute Oral Toxicity (c)	III	0.6459	64.59%
Estrogen receptor binding	+	0.6311	63.11%
Androgen receptor binding	+	0.7497	74.97%
Thyroid receptor binding	+	0.6961	69.61%
Glucocorticoid receptor binding	+	0.7964	79.64%
Aromatase binding	+	0.7089	70.89%
PPAR gamma	+	0.7915	79.15%
Honey bee toxicity	-	0.6704	67.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.03%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.63%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.83%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.45%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.33%	96.77%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.46%	93.00%
CHEMBL2581	P07339	Cathepsin D	88.11%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.66%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.62%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.43%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.96%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.63%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.92%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.86%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.72%	99.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.52%	100.00%

Plants that contains it

• Aspilia kotschyi

Cross-Links

• PubChem: 162918344
• LOTUS: LTS0095483
• wikiData: Q105005827