(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylpropanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid

Details

• Internal ID: aec66be1-27be-4646-9468-76c7b3375b07
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylpropanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
• SMILES (Canonical): CC(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)COC(=O)C)O
• SMILES (Isomeric): CC(C)C(=O)O[C@H]1[C@@H]([C@@]2([C@@H](C[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)C)C)[C@@H]2CC1(C)C)C)O)COC(=O)C)O
• InChI: InChI=1S/C54H86O24/c1-22(2)45(70)78-43-42(67)54(21-71-23(3)58)25(16-49(43,4)5)24-10-11-29-50(6)14-13-31(51(7,20-57)28(50)12-15-52(29,8)53(24,9)17-30(54)59)74-48-40(76-47-37(65)35(63)33(61)27(19-56)73-47)38(66)39(41(77-48)44(68)69)75-46-36(64)34(62)32(60)26(18-55)72-46/h10,22,25-43,46-48,55-57,59-67H,11-21H2,1-9H3,(H,68,69)/t25-,26+,27+,28+,29+,30+,31-,32-,33-,34-,35-,36+,37+,38-,39-,40+,41-,42-,43-,46-,47-,48+,50-,51+,52+,53+,54-/m0/s1
• InChI Key: MHHWTELKJZFCGI-REMMCLCSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₄
• Molecular Weight: 1119.20 g/mol
• Exact Mass: 1118.55090361 g/mol
• Topological Polar Surface Area (TPSA): 388.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.63
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8735	87.35%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8050	80.50%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9312	93.12%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	+	0.5651	56.51%
CYP3A4 substrate	+	0.7344	73.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7712	77.12%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7188	71.88%
Human Ether-a-go-go-Related Gene inhibition	+	0.7439	74.39%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7783	77.83%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.5106	51.06%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7603	76.03%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	+	0.5781	57.81%
Glucocorticoid receptor binding	+	0.7842	78.42%
Aromatase binding	+	0.6367	63.67%
PPAR gamma	+	0.8134	81.34%
Honey bee toxicity	-	0.6452	64.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	97.35%	91.11%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	96.32%	91.65%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.07%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.02%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.13%	97.36%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.25%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.88%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.49%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.04%	86.33%
CHEMBL5028	O14672	ADAM10	86.83%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.44%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.41%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.50%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.37%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.34%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.98%	95.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.66%	95.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.61%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.26%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.15%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	81.59%	94.73%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.04%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.65%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.13%	93.00%

Plants that contains it

• Aesculus hippocastanum

Cross-Links

• PubChem: 100917539
• LOTUS: LTS0118117
• wikiData: Q105163822