(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aR,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-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 5fcdec19-4905-42f1-be89-89bd8b1e50b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aR,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-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)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)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C54H86O24/c1-49(2)14-16-54(48(70)78-46-38(66)35(63)32(60)26(21-57)73-46)17-15-52(6)22(23(54)18-49)8-9-28-51(5)12-11-29(50(3,4)27(51)10-13-53(28,52)7)74-47-42(77-45-37(65)34(62)31(59)25(20-56)72-45)40(39(67)41(76-47)43(68)69)75-44-36(64)33(61)30(58)24(19-55)71-44/h8,23-42,44-47,55-67H,9-21H2,1-7H3,(H,68,69)/t23-,24-,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+/m1/s1
• InChI Key: YSCJAYPKBYRXEZ-HTGJWXJPSA-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): 391.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 23
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7181	71.81%
Caco-2	-	0.8813	88.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8914	89.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7282	72.82%
OATP1B3 inhibitior	-	0.5187	51.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5974	59.74%
BSEP inhibitior	+	0.8330	83.30%
P-glycoprotein inhibitior	+	0.7485	74.85%
P-glycoprotein substrate	-	0.8507	85.07%
CYP3A4 substrate	+	0.7148	71.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.8653	86.53%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.8749	87.49%
CYP2C8 inhibition	+	0.7158	71.58%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6115	61.15%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.6295	62.95%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6973	69.73%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9697	96.97%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8912	89.12%
Acute Oral Toxicity (c)	III	0.7689	76.89%
Estrogen receptor binding	+	0.7770	77.70%
Androgen receptor binding	+	0.7443	74.43%
Thyroid receptor binding	-	0.4925	49.25%
Glucocorticoid receptor binding	+	0.7659	76.59%
Aromatase binding	+	0.6318	63.18%
PPAR gamma	+	0.8051	80.51%
Honey bee toxicity	-	0.6901	69.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9722	97.22%

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	97.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.65%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.21%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.89%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.37%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	86.04%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.24%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.87%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.33%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.10%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.95%	95.50%

Plants that contains it

• Calendula arvensis

Cross-Links

• PubChem: 162980388
• LOTUS: LTS0268260
• wikiData: Q105359520