Oleanolic Acid (Caryophyllin)
| Internal ID | 4857bc51-6e5e-40a9-9e4d-cdcf8adf4f69 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Triterpenoids |
| IUPAC Name | (4R,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4-carboxylic acid |
| SMILES (Canonical) | CC1(CC2C(CCC3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C)C(C1)C(=O)O)C |
| SMILES (Isomeric) | C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CCC5[C@H]4CC(C[C@H]5C(=O)O)(C)C)C)C)(C)C)O |
| InChI | InChI=1S/C30H48O3/c1-26(2)16-19-18(20(17-26)25(32)33)10-14-29(6)21(19)8-9-23-28(5)13-12-24(31)27(3,4)22(28)11-15-30(23,29)7/h8,18-20,22-24,31H,9-17H2,1-7H3,(H,32,33)/t18?,19-,20-,22+,23-,24+,28+,29-,30-/m1/s1 |
| InChI Key | AOWMBRPPHGNFDX-HPPBOAITSA-N |
| Popularity | 4 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 | 7.60 |
| Atomic LogP (AlogP) | 7.09 |
| H-Bond Acceptor | 2 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 1 |
| SCHEMBL1699365 |
| s2334 |
| AKOS022168208 |
| CCG-269304 |
| NCGC00346594-02 |
| AS-11663 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9972 | 99.72% |
| Caco-2 | - | 0.5536 | 55.36% |
| Blood Brain Barrier | - | 0.7500 | 75.00% |
| Human oral bioavailability | + | 0.5857 | 58.57% |
| Subcellular localzation | Mitochondria | 0.8699 | 86.99% |
| OATP2B1 inhibitior | - | 0.7138 | 71.38% |
| OATP1B1 inhibitior | + | 0.9027 | 90.27% |
| OATP1B3 inhibitior | + | 0.9479 | 94.79% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | + | 0.6000 | 60.00% |
| BSEP inhibitior | + | 0.8753 | 87.53% |
| P-glycoprotein inhibitior | - | 0.7246 | 72.46% |
| P-glycoprotein substrate | - | 0.8443 | 84.43% |
| CYP3A4 substrate | + | 0.6558 | 65.58% |
| 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 | + | 0.4580 | 45.80% |
| CYP inhibitory promiscuity | - | 0.9046 | 90.46% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.5962 | 59.62% |
| Eye corrosion | - | 0.9948 | 99.48% |
| Eye irritation | - | 0.9402 | 94.02% |
| Skin irritation | + | 0.6328 | 63.28% |
| Skin corrosion | - | 0.9644 | 96.44% |
| Ames mutagenesis | - | 0.8500 | 85.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5098 | 50.98% |
| Micronuclear | - | 0.8500 | 85.00% |
| Hepatotoxicity | - | 0.6750 | 67.50% |
| skin sensitisation | + | 0.5630 | 56.30% |
| Respiratory toxicity | + | 0.6889 | 68.89% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.8125 | 81.25% |
| Nephrotoxicity | - | 0.7256 | 72.56% |
| Acute Oral Toxicity (c) | III | 0.8316 | 83.16% |
| Estrogen receptor binding | + | 0.7391 | 73.91% |
| Androgen receptor binding | + | 0.7500 | 75.00% |
| Thyroid receptor binding | + | 0.5827 | 58.27% |
| Glucocorticoid receptor binding | + | 0.8261 | 82.61% |
| Aromatase binding | + | 0.7252 | 72.52% |
| PPAR gamma | + | 0.6029 | 60.29% |
| Honey bee toxicity | - | 0.8607 | 86.07% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | - | 0.5900 | 59.00% |
| Fish aquatic toxicity | + | 0.9956 | 99.56% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.91% | 96.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 91.13% | 91.11% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.04% | 95.56% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 87.83% | 93.00% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 86.75% | 97.09% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 86.75% | 100.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 85.75% | 98.95% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 84.87% | 94.45% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 84.67% | 90.17% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 83.22% | 97.25% |
| CHEMBL5028 | O14672 | ADAM10 | 81.93% | 97.50% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 80.43% | 96.77% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 80.37% | 91.19% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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