oleanolic acid 3-O-[O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->3)-O-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranoside]

Details

• Internal ID: 4b7cacc5-9d60-45b0-9da5-ecb109f8256c
• 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)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-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)OC9C(C(C(C(O9)CO)O)O)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[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C53H86O21/c1-23-32(57)41(73-44-38(63)36(61)40(28(21-55)70-44)72-43-37(62)35(60)34(59)27(20-54)69-43)39(64)45(68-23)74-42-33(58)26(56)22-67-46(42)71-31-12-13-50(6)29(49(31,4)5)11-14-52(8)30(50)10-9-24-25-19-48(2,3)15-17-53(25,47(65)66)18-16-51(24,52)7/h9,23,25-46,54-64H,10-22H2,1-8H3,(H,65,66)/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,40+,41+,42+,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
• InChI Key: VDRZQZWUCOHKED-BXROMGGZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₁
• Molecular Weight: 1059.20 g/mol
• Exact Mass: 1058.56615975 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.20
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• 244202-36-6
• CHEBI:66818
• oleanolic acid 3-O-[O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->3)-O-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranoside]
• (3beta)-3-{[beta-D-glucopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->3)-6-deoxy-alpha-L-mannopyranosyl-(1->2)-alpha-L-arabinopyranosyl]oxy}olean-12-en-28-oic acid
• CHEMBL448368
• VDRZQZWUCOHKED-BXROMGGZSA-
• HY-N8098
• AKOS040762248
• CS-0139945
• D84971
• Q27135451
• 3beta-[[2-O-[3-O-(4-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)-alpha-L-rhamnopyranosyl]-alpha-L-arabinopyranosyl]oxy]oleana-12-ene-28-oic acid
• InChI=1/C53H86O21/c1-23-32(57)41(73-44-38(63)36(61)40(28(21-55)70-44)72-43-37(62)35(60)34(59)27(20-54)69-43)39(64)45(68-23)74-42-33(58)26(56)22-67-46(42)71-31-12-13-50(6)29(49(31,4)5)11-14-52(8)30(50)10-9-24-25-19-48(2,3)15-17-53(25,47(65)66)18-16-51(24,5
• OLEANOLIC ACID - 3-O-| cent-D- GALACTOSYL( 1 inverted exclamation marku3)-| cent-D-GLUCOSYL( 1 inverted exclamation marku3)-| inverted exclamation mark-L-RHAMNOSYL(1 inverted exclamation marku2)-| inverted exclamation mark-L-ARABINOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8771	87.71%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3185	31.85%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8828	88.28%
P-glycoprotein inhibitior	+	0.7465	74.65%
P-glycoprotein substrate	-	0.6681	66.81%
CYP3A4 substrate	+	0.7275	72.75%
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	+	0.7098	70.98%
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	-	0.9017	90.17%
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	+	0.7445	74.45%
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	-	0.9480	94.80%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8038	80.38%
Androgen receptor binding	+	0.7298	72.98%
Thyroid receptor binding	+	0.5348	53.48%
Glucocorticoid receptor binding	+	0.7354	73.54%
Aromatase binding	+	0.6532	65.32%
PPAR gamma	+	0.8089	80.89%
Honey bee toxicity	-	0.6780	67.80%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5805	58.05%
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	95.41%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.85%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.65%	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%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.25%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	85.29%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.56%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.36%	96.77%
CHEMBL5028	O14672	ADAM10	82.87%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.36%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.34%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.09%	95.50%

Plants that contains it

• Pulsatilla chinensis

Cross-Links

• PubChem: 11766614
• NPASS: NPC251263
• ChEMBL: CHEMBL448368
• LOTUS: LTS0121971
• wikiData: Q27135451