Olean-12-en-28-oic acid, 3-(alpha-L-arabinopyranosyloxy)-, 6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl ester, (3beta)-

Details

• Internal ID: a6816ed7-1727-4892-8771-c097b1b2bdab
• 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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-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)C)OC6C(C(C(CO6)O)O)O)C)C)C2C1)C)C(=O)OC7C(C(C(C(O7)COC8C(C(C(C(O8)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](CO8)O)O)O
• InChI: InChI=1S/C47H76O17/c1-42(2)14-16-47(41(58)64-40-37(57)34(54)32(52)26(62-40)21-60-38-36(56)33(53)31(51)25(19-48)61-38)17-15-45(6)22(23(47)18-42)8-9-28-44(5)12-11-29(43(3,4)27(44)10-13-46(28,45)7)63-39-35(55)30(50)24(49)20-59-39/h8,23-40,48-57H,9-21H2,1-7H3/t23-,24-,25+,26+,27-,28+,29-,30-,31+,32+,33-,34-,35+,36+,37+,38+,39-,40-,44-,45+,46+,47-/m0/s1
• InChI Key: NFIQKUQYFSTGFU-VWZQPUASSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• Asperosaponin V
• Olean-12-en-28-oic acid, 3-(alpha-L-arabinopyranosyloxy)-, 6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl ester, (3beta)-
• CHEMBL4443030
• DTXSID801316921
• 3beta-(alpha-L-Arabinopyranosyloxy)olean-12-en-28-oic acid 6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8872	88.72%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7721	77.21%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.5939	59.39%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	-	0.7567	75.67%
CYP3A4 substrate	+	0.7258	72.58%
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	+	0.6616	66.16%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6991	69.91%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8800	88.00%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7792	77.92%
Androgen receptor binding	+	0.7288	72.88%
Thyroid receptor binding	-	0.5500	55.00%
Glucocorticoid receptor binding	+	0.7109	71.09%
Aromatase binding	+	0.6344	63.44%
PPAR gamma	+	0.7820	78.20%
Honey bee toxicity	-	0.7049	70.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6105	61.05%
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	98.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.77%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.24%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.60%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.19%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.09%	95.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.82%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	87.05%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.93%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.92%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.63%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.66%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.46%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.93%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.64%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.11%	97.36%
CHEMBL5028	O14672	ADAM10	80.31%	97.50%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 101623719
• NPASS: NPC87172
• LOTUS: LTS0006048
• wikiData: Q105178493