I(2)-D-Glucopyranosyl (3I(2),4I+/-)-3-[(2-O-I(2)-D-glucopyranosyl-I+/--L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oate

Details

• Internal ID: cfc38d45-8147-4c64-a71b-687d0ab9358b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)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)CO)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C47H76O18/c1-42(2)13-15-47(41(59)65-39-36(58)34(56)32(54)26(19-49)62-39)16-14-45(5)22(23(47)17-42)7-8-28-43(3)11-10-29(44(4,21-50)27(43)9-12-46(28,45)6)63-40-37(30(52)24(51)20-60-40)64-38-35(57)33(55)31(53)25(18-48)61-38/h7,23-40,48-58H,8-21H2,1-6H3/t23-,24-,25+,26+,27+,28+,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,43-,44-,45+,46+,47-/m0/s1
• InChI Key: KOQPPOSSMNKJPO-YWBCTTEYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₈
• Molecular Weight: 929.10 g/mol
• Exact Mass: 928.50316557 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 141492-08-2
• beta-D-Glucopyranosyl (3beta,4alpha)-3-[(2-O-beta-D-glucopyranosyl-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8900	89.00%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8785	87.85%
OATP1B1 inhibitior	+	0.8684	86.84%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.4704	47.04%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	-	0.7306	73.06%
CYP3A4 substrate	+	0.7302	73.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6604	66.04%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9057	90.57%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7422	74.22%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7414	74.14%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7905	79.05%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	-	0.5921	59.21%
Glucocorticoid receptor binding	+	0.7121	71.21%
Aromatase binding	+	0.6440	64.40%
PPAR gamma	+	0.7831	78.31%
Honey bee toxicity	-	0.7026	70.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	97.28%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.74%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.30%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.01%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.04%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.31%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.24%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.17%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.35%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.69%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.48%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.14%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.81%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.42%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	81.06%	92.50%
CHEMBL5028	O14672	ADAM10	80.73%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.18%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.08%	97.25%

Plants that contains it

• Medicago arabica
• Medicago polymorpha
• Medicago sativa

Cross-Links

• PubChem: 101623722
• LOTUS: LTS0237167
• wikiData: Q105143948