Oleanolic acid 3-O-beta-D-glucosyl-(1->3)-alpha-L-rhamnosyl(1->2)-alpha-L-arabinoside

Details

• Internal ID: 7d68c64d-14e0-4d8a-8803-f18f63b6e039
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O
• InChI: InChI=1S/C47H76O16/c1-22-30(50)36(62-38-34(54)33(53)32(52)26(20-48)60-38)35(55)39(59-22)63-37-31(51)25(49)21-58-40(37)61-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57)/t22-,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: OHJWWOZXCKEOGK-YDOLDEOXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₆
• Molecular Weight: 897.10 g/mol
• Exact Mass: 896.51333633 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• Oleanolic acid 3-O-beta-D-glucosyl-(1->3)-alpha-L-rhamnosyl(1->2)-alpha-L-arabinoside
• (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CHEMBL475806
• OHJWWOZXCKEOGK-YDOLDEOXSA-N
• AKOS040760606
• (3| cent)-3-[(O-|A-D-glucopyranosyl-(1 inverted exclamation marku3)-O-6-deoxy-|A-L-mannopyranosyl-(1 inverted exclamation marku2)-|A-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid
• 3beta-[2-O-(3-O-beta-D-Glucopyranosyl-alpha-L-rhamnopyranosyl)-alpha-L-arabinopyranosyloxy]oleana-12-ene-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8864	88.64%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8799	87.99%
OATP1B1 inhibitior	-	0.3510	35.10%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7929	79.29%
P-glycoprotein inhibitior	+	0.7520	75.20%
P-glycoprotein substrate	-	0.7077	70.77%
CYP3A4 substrate	+	0.7228	72.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
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	+	0.6852	68.52%
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	-	0.9078	90.78%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6532	65.32%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9154	91.54%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.7218	72.18%
Thyroid receptor binding	-	0.5658	56.58%
Glucocorticoid receptor binding	+	0.7079	70.79%
Aromatase binding	+	0.6681	66.81%
PPAR gamma	+	0.7749	77.49%
Honey bee toxicity	-	0.7010	70.10%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6005	60.05%
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	97.63%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.53%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.94%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.52%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.78%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.26%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.21%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.62%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL5028	O14672	ADAM10	82.87%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.82%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.65%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.36%	100.00%

Plants that contains it

• Pulsatilla cernua
• Pulsatilla chinensis

Cross-Links

• PubChem: 11722070
• NPASS: NPC292677
• ChEMBL: CHEMBL475806
• LOTUS: LTS0088712
• wikiData: Q105192120