Oleanolic Acid
| Internal ID | 55d28c09-4c89-4422-960a-f3bf14729019 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Triterpenoids |
| IUPAC Name | (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-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) | CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=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)C)(C)C)O |
| InChI | InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1 |
| InChI Key | MIJYXULNPSFWEK-GTOFXWBISA-N |
| Popularity | 8,207 references in papers |
| Molecular Formula | C30H48O3 |
| Molecular Weight | 456.70 g/mol |
| Exact Mass | 456.36034539 g/mol |
| Topological Polar Surface Area (TPSA) | 57.50 Ų |
| XlogP | 7.50 |
| Atomic LogP (AlogP) | 7.23 |
| H-Bond Acceptor | 2 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 1 |
| 508-02-1 |
| Oleanic acid |
| Caryophyllin |
| Astrantiagenin C |
| Giganteumgenin C |
| Virgaureagenin B |
| 3beta-Hydroxyolean-12-en-28-oic acid |
| Oleanol |
| oleonolic acid |
| 3-beta-Hydroxyolean-12-en-28-oic acid |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9972 | 99.72% |
| Caco-2 | + | 0.5596 | 55.96% |
| Blood Brain Barrier | - | 0.7500 | 75.00% |
| Human oral bioavailability | + | 0.5429 | 54.29% |
| Subcellular localzation | Mitochondria | 0.8699 | 86.99% |
| OATP2B1 inhibitior | - | 0.7192 | 71.92% |
| OATP1B1 inhibitior | + | 0.8808 | 88.08% |
| OATP1B3 inhibitior | + | 0.9479 | 94.79% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | + | 0.6000 | 60.00% |
| BSEP inhibitior | + | 0.9111 | 91.11% |
| P-glycoprotein inhibitior | - | 0.9165 | 91.65% |
| P-glycoprotein substrate | - | 0.9082 | 90.82% |
| CYP3A4 substrate | + | 0.6412 | 64.12% |
| CYP2C9 substrate | - | 0.8404 | 84.04% |
| CYP2D6 substrate | - | 0.8509 | 85.09% |
| CYP3A4 inhibition | - | 0.8695 | 86.95% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9025 | 90.25% |
| CYP2D6 inhibition | - | 0.9485 | 94.85% |
| CYP1A2 inhibition | - | 0.9169 | 91.69% |
| CYP2C8 inhibition | - | 0.7001 | 70.01% |
| CYP inhibitory promiscuity | - | 0.9046 | 90.46% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.5962 | 59.62% |
| Eye corrosion | - | 0.9948 | 99.48% |
| Eye irritation | - | 0.9085 | 90.85% |
| Skin irritation | + | 0.6328 | 63.28% |
| Skin corrosion | - | 0.9644 | 96.44% |
| Ames mutagenesis | - | 0.9600 | 96.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5287 | 52.87% |
| Micronuclear | - | 0.8500 | 85.00% |
| Hepatotoxicity | - | 0.8125 | 81.25% |
| skin sensitisation | + | 0.5630 | 56.30% |
| Respiratory toxicity | + | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.8125 | 81.25% |
| Nephrotoxicity | - | 0.7559 | 75.59% |
| Acute Oral Toxicity (c) | III | 0.8316 | 83.16% |
| Estrogen receptor binding | + | 0.8127 | 81.27% |
| Androgen receptor binding | + | 0.6710 | 67.10% |
| Thyroid receptor binding | + | 0.6460 | 64.60% |
| Glucocorticoid receptor binding | + | 0.8447 | 84.47% |
| Aromatase binding | + | 0.6767 | 67.67% |
| PPAR gamma | + | 0.6306 | 63.06% |
| Honey bee toxicity | - | 0.8853 | 88.53% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | - | 0.6100 | 61.00% |
| Fish aquatic toxicity | + | 0.9956 | 99.56% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL5983 | O60218 | Aldo-keto reductase family 1 member B10 |
72 nM 90 nM 4000 nM |
Ki IC50 IC50 |
via Super-PRED
PMID: 21561086 PMID: 21561086 |
| CHEMBL2047 | Q96RI1 | Bile acid receptor FXR |
0 nM |
EC50 |
PMID: 19911773
|
| CHEMBL4081 | P13726 | Coagulation factor III |
4.975 nM |
IC50 |
via Super-PRED
|
| CHEMBL2392 | P06746 | DNA polymerase beta |
8800 nM 3000 nM 8800 nM 24980 nM |
IC50 IC50 IC50 IC50 |
PMID: 15217274
PMID: 21561086 PMID: 14640519 PMID: 18343122 |
| CHEMBL4804 | P30305 | Dual specificity phosphatase Cdc25B |
980 nM 980 nM |
IC50 IC50 |
PMID: 25497963
via Super-PRED |
| CHEMBL5409 | Q8TDU6 | G-protein coupled bile acid receptor 1 |
2250 nM |
EC50 |
PMID: 19911773
|
| CHEMBL4903 | P24666 | Low molecular weight phosphotyrosine protein phosphatase |
21200 nM 22900 nM 22900 nM 21200 nM |
IC50 IC50 IC50 IC50 |
PMID: 21453996
PMID: 21453996 PMID: 25264584 PMID: 25264584 |
| CHEMBL4426 | P04054 | Phospholipase A2 group 1B |
3000 nM |
IC50 |
PMID: 21561086
|
| CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B |
5050.1 nM 3370 nM 1536 nM 3020 nM 1170 nM 730 nM 1536 nM 700 nM 700 nM 1536 nM 2600 nM 1100 nM 3020 nM 2010 nM 1900 nM 4200 nM 5600 nM 3840 nM 3370 nM 3020 nM 1030 nM 3020 nM 3900 nM 1000 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
DOI: 10.1007/s00044-010-9529-5
DOI: 10.1007/s00044-010-9529-5 PMID: 27123900 PMID: 26774579 PMID: 25600405 PMID: 26711144 PMID: 26481657 PMID: 26253631 PMID: 26115570 PMID: 26100442 PMID: 23357636 PMID: 23434422 PMID: 23942421 PMID: 24090912 PMID: 24684845 PMID: 19702283 PMID: 22690646 PMID: 22044245 PMID: 18707891 PMID: 25497963 PMID: 25595683 PMID: 25872983 PMID: 16580200 PMID: 26083682 |
| CHEMBL3166 | P29350 | Protein-tyrosine phosphatase 1C |
14190 nM 31330 nM |
IC50 IC50 |
PMID: 27123900
PMID: 18707891 |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C |
11620 nM |
IC50 |
PMID: 27123900
|
| CHEMBL3521 | P10586 | Receptor-type tyrosine-protein phosphatase F (LAR) |
22310 nM 11800 nM |
IC50 IC50 |
PMID: 27123900
PMID: 21453996 |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase |
4230 nM 5460 nM 4440 nM 5460 nM 5460 nM |
IC50 IC50 IC50 IC50 IC50 |
PMID: 24684845
PMID: 27123900 PMID: 25497963 PMID: 26481657 PMID: 26100442 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 93.38% | 90.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.20% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 90.13% | 97.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 88.78% | 91.11% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 88.68% | 94.45% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 87.96% | 95.56% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 84.80% | 96.77% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 83.76% | 100.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 82.43% | 98.95% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 81.92% | 93.00% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 10494 |
| NPASS | NPC142415 |
| ChEMBL | CHEMBL168 |
| LOTUS | LTS0112895 |
| wikiData | Q105191782 |