(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4-formyl-4,6a,6b,11,11,14b-hexamethyl-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]-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: a4f018b3-0f90-4d21-8648-f900e8aba7cc
• 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,8aS,12aS,14aR,14bR)-4-formyl-4,6a,6b,11,11,14b-hexamethyl-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]-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C=O)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)C)C2C1)C)C(=O)OC7C(C(C(C(O7)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)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O
• InChI: InChI=1S/C42H64O15/c1-37(2)13-15-42(36(53)57-34-30(49)27(46)26(45)22(18-43)54-34)16-14-40(5)20(21(42)17-37)7-8-24-38(3)11-10-25(39(4,19-44)23(38)9-12-41(24,40)6)55-35-31(50)28(47)29(48)32(56-35)33(51)52/h7,19,21-32,34-35,43,45-50H,8-18H2,1-6H3,(H,51,52)/t21-,22+,23+,24+,25-,26+,27-,28-,29-,30+,31+,32-,34-,35+,38-,39-,40+,41+,42-/m0/s1
• InChI Key: KFNNEUAROQLUQS-ZJDNFKTFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₁₅
• Molecular Weight: 808.90 g/mol
• Exact Mass: 808.42452133 g/mol
• Topological Polar Surface Area (TPSA): 250.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 3beta-(beta-D-Glucopyranuronosyloxy)-23-oxooleana-12-ene-28-oic acid 28-beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7941	79.41%
Caco-2	-	0.8782	87.82%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8948	89.48%
OATP2B1 inhibitior	-	0.8731	87.31%
OATP1B1 inhibitior	+	0.7846	78.46%
OATP1B3 inhibitior	-	0.5056	50.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6474	64.74%
BSEP inhibitior	+	0.6425	64.25%
P-glycoprotein inhibitior	+	0.7633	76.33%
P-glycoprotein substrate	-	0.8007	80.07%
CYP3A4 substrate	+	0.7054	70.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8459	84.59%
CYP2C9 inhibition	-	0.8380	83.80%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8499	84.99%
CYP2C8 inhibition	+	0.7115	71.15%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6298	62.98%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9088	90.88%
Skin irritation	-	0.5723	57.23%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7277	72.77%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8727	87.27%
Acute Oral Toxicity (c)	III	0.7628	76.28%
Estrogen receptor binding	+	0.7345	73.45%
Androgen receptor binding	+	0.7372	73.72%
Thyroid receptor binding	-	0.5778	57.78%
Glucocorticoid receptor binding	+	0.7098	70.98%
Aromatase binding	+	0.6090	60.90%
PPAR gamma	+	0.7527	75.27%
Honey bee toxicity	-	0.7399	73.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9778	97.78%

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	96.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.02%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.92%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.50%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.54%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.34%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.87%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.26%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.21%	94.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.82%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.79%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.91%	97.36%
CHEMBL5028	O14672	ADAM10	80.74%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.61%	95.50%
CHEMBL4302	P08183	P-glycoprotein 1	80.49%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%

Plants that contains it

• Eleutherococcus senticosus
• Salicornia depressa
• Salicornia europaea
• Swartzia simplex

Cross-Links

• PubChem: 70692466
• NPASS: NPC242840
• ChEMBL: CHEMBL2043373
• LOTUS: LTS0153847
• wikiData: Q105140491