(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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 39bf73e5-2698-4eb4-a845-cd909ccfe434
• 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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-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(CO7)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)O)O)O[C@@H]9[C@@H]([C@H]([C@H](CO9)O)O)O)O
• InChI: InChI=1S/C53H84O23/c1-48(2)14-16-53(47(68)76-45-37(63)34(60)32(58)26(72-45)21-70-43-36(62)33(59)31(57)25(19-54)71-43)17-15-51(6)22(23(53)18-48)8-9-28-50(5)12-11-29(49(3,4)27(50)10-13-52(28,51)7)73-46-39(65)40(38(64)41(75-46)42(66)67)74-44-35(61)30(56)24(55)20-69-44/h8,23-41,43-46,54-65H,9-21H2,1-7H3,(H,66,67)/t23-,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,38+,39-,40+,41+,43-,44-,45+,46-,50+,51-,52-,53+/m1/s1
• InChI Key: ZLWLOHPUYLUMPQ-HMHZGXCESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₄O₂₃
• Molecular Weight: 1089.20 g/mol
• Exact Mass: 1088.54033892 g/mol
• Topological Polar Surface Area (TPSA): 371.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 11

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	-	0.8791	87.91%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7609	76.09%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8138	81.38%
P-glycoprotein inhibitior	+	0.7486	74.86%
P-glycoprotein substrate	-	0.6515	65.15%
CYP3A4 substrate	+	0.7323	73.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
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	+	0.7616	76.16%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7116	71.16%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9251	92.51%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7831	78.31%
Androgen receptor binding	+	0.7398	73.98%
Thyroid receptor binding	+	0.5425	54.25%
Glucocorticoid receptor binding	+	0.7683	76.83%
Aromatase binding	+	0.6537	65.37%
PPAR gamma	+	0.8166	81.66%
Honey bee toxicity	-	0.6665	66.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
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	98.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.12%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.38%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.75%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.74%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.08%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	88.77%	95.93%
CHEMBL2581	P07339	Cathepsin D	88.33%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	86.12%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.77%	95.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.70%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.44%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.59%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.51%	100.00%
CHEMBL5028	O14672	ADAM10	83.12%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.71%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.10%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.96%	94.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.53%	97.36%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.51%	93.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.28%	83.57%

Plants that contains it

• Hemsleya graciliflora

Cross-Links

• PubChem: 162977294
• LOTUS: LTS0224526
• wikiData: Q105379245