methyl (2S,3S,4R,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-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate

Details

• Internal ID: b2458654-15c1-466b-a350-28efe2b46e0d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (2S,3S,4R,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-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S,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)OC7C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)O)C)C)C2C1)C)C(=O)OC9C(C(C(C(O9)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[C@H]8[C@@H]([C@H]([C@@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
• InChI: InChI=1S/C54H86O23/c1-49(2)15-17-54(48(68)77-46-38(65)35(62)32(59)26(21-56)72-46)18-16-52(6)23(24(54)19-49)9-10-29-51(5)13-12-30(50(3,4)28(51)11-14-53(29,52)7)73-47-39(66)40(74-45-37(64)34(61)31(58)25(20-55)70-45)41(42(76-47)43(67)69-8)75-44-36(63)33(60)27(22-57)71-44/h9,24-42,44-47,55-66H,10-22H2,1-8H3/t24-,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,35-,36+,37+,38+,39+,40+,41-,42-,44-,45-,46-,47+,51-,52+,53+,54-/m0/s1
• InChI Key: IEWLKNYJNWFEKE-IGDMNXAZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₃
• Molecular Weight: 1103.20 g/mol
• Exact Mass: 1102.55598899 g/mol
• Topological Polar Surface Area (TPSA): 360.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8799	87.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8743	87.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7289	72.89%
OATP1B3 inhibitior	+	0.8514	85.14%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9236	92.36%
P-glycoprotein inhibitior	+	0.7506	75.06%
P-glycoprotein substrate	-	0.7757	77.57%
CYP3A4 substrate	+	0.7294	72.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8735	87.35%
CYP3A4 inhibition	-	0.8952	89.52%
CYP2C9 inhibition	-	0.8464	84.64%
CYP2C19 inhibition	-	0.8975	89.75%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.8952	89.52%
CYP2C8 inhibition	+	0.6968	69.68%
CYP inhibitory promiscuity	-	0.9266	92.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4843	48.43%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.6018	60.18%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7198	71.98%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9572	95.72%
skin sensitisation	-	0.9041	90.41%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7651	76.51%
Acute Oral Toxicity (c)	III	0.6253	62.53%
Estrogen receptor binding	+	0.7743	77.43%
Androgen receptor binding	+	0.7479	74.79%
Thyroid receptor binding	+	0.5234	52.34%
Glucocorticoid receptor binding	+	0.7845	78.45%
Aromatase binding	+	0.6465	64.65%
PPAR gamma	+	0.8117	81.17%
Honey bee toxicity	-	0.6545	65.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9617	96.17%

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	98.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.54%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.56%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.54%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.36%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.12%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.60%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.60%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.45%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	84.11%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.60%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.85%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.35%	96.21%

Plants that contains it

• Aralia elata
• Panax bipinnatifidus

Cross-Links

• PubChem: 101665688
• LOTUS: LTS0258407
• wikiData: Q105112003