Ursolic Acid
| Internal ID | f0fa70b4-c15c-4378-aaf0-500c179f56a6 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Triterpenoids |
| IUPAC Name | (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid |
| SMILES (Canonical) | CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O |
| SMILES (Isomeric) | C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O |
| InChI | InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 |
| InChI Key | WCGUUGGRBIKTOS-GPOJBZKASA-N |
| Popularity | 2,055 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 | 7.30 |
| Atomic LogP (AlogP) | 7.09 |
| H-Bond Acceptor | 2 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 1 |
| 77-52-1 |
| Prunol |
| Malol |
| Urson |
| 3beta-Hydroxyurs-12-en-28-oic acid |
| Micromerol |
| (3beta)-3-Hydroxyurs-12-en-28-oic acid |
| NSC-4060 |
| CCRIS 7123 |
| CHEBI:9908 |
| 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 | + | 0.6086 | 60.86% |
| Blood Brain Barrier | - | 0.7500 | 75.00% |
| Human oral bioavailability | + | 0.5143 | 51.43% |
| Subcellular localzation | Mitochondria | 0.8699 | 86.99% |
| OATP2B1 inhibitior | - | 0.7168 | 71.68% |
| OATP1B1 inhibitior | + | 0.9413 | 94.13% |
| OATP1B3 inhibitior | + | 0.9479 | 94.79% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | + | 0.6000 | 60.00% |
| BSEP inhibitior | + | 0.8278 | 82.78% |
| P-glycoprotein inhibitior | - | 0.9166 | 91.66% |
| P-glycoprotein substrate | - | 0.8292 | 82.92% |
| CYP3A4 substrate | + | 0.6600 | 66.00% |
| 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 | - | 0.5587 | 55.87% |
| CYP inhibitory promiscuity | - | 0.9046 | 90.46% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.5962 | 59.62% |
| Eye corrosion | - | 0.9948 | 99.48% |
| Eye irritation | - | 0.9387 | 93.87% |
| Skin irritation | + | 0.6328 | 63.28% |
| Skin corrosion | - | 0.9644 | 96.44% |
| Ames mutagenesis | - | 0.9000 | 90.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4928 | 49.28% |
| Micronuclear | - | 0.8500 | 85.00% |
| Hepatotoxicity | + | 0.5916 | 59.16% |
| skin sensitisation | + | 0.5630 | 56.30% |
| Respiratory toxicity | - | 0.5000 | 50.00% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.8125 | 81.25% |
| Nephrotoxicity | - | 0.8450 | 84.50% |
| Acute Oral Toxicity (c) | III | 0.8316 | 83.16% |
| Estrogen receptor binding | + | 0.7492 | 74.92% |
| Androgen receptor binding | + | 0.7283 | 72.83% |
| Thyroid receptor binding | + | 0.6846 | 68.46% |
| Glucocorticoid receptor binding | + | 0.8495 | 84.95% |
| Aromatase binding | + | 0.6607 | 66.07% |
| PPAR gamma | + | 0.5573 | 55.73% |
| Honey bee toxicity | - | 0.8551 | 85.51% |
| Biodegradation | - | 0.7750 | 77.50% |
| Crustacea aquatic toxicity | - | 0.5500 | 55.00% |
| Fish aquatic toxicity | + | 0.9956 | 99.56% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL4235 | P28845 | 11-beta-hydroxysteroid dehydrogenase 1 |
1900 nM |
IC50 |
PMID: 20100662
|
| CHEMBL5983 | O60218 | Aldo-keto reductase family 1 member B10 |
4000 nM |
IC50 |
PMID: 21561086
|
| CHEMBL1900 | P15121 | Aldose reductase |
41000 nM |
IC50 |
PMID: 21561086
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
158.5 nM 158.5 nM |
Potency Potency |
via CMAUP
via Super-PRED |
| CHEMBL2047 | Q96RI1 | Bile acid receptor FXR |
0 nM |
EC50 |
PMID: 19911773
|
| CHEMBL2581 | P07339 | Cathepsin D |
18200 nM |
IC50 |
DOI: 10.1007/s00044-012-0397-z
|
| CHEMBL1978 | P11511 | Cytochrome P450 19A1 |
32000 nM |
IC50 |
PMID: 18192087
|
| CHEMBL2392 | P06746 | DNA polymerase beta |
18600 nM |
IC50 |
PMID: 15165161
|
| CHEMBL5409 | Q8TDU6 | G-protein coupled bile acid receptor 1 |
1430 nM |
EC50 |
PMID: 19911773
|
| CHEMBL4903 | P24666 | Low molecular weight phosphotyrosine protein phosphatase |
11100 nM 7200 nM |
IC50 IC50 |
PMID: 21453996
PMID: 21453996 |
| CHEMBL5533 | Q04206 | Nuclear factor NF-kappa-B p65 subunit |
31 nM |
IC50 |
via Super-PRED
|
| CHEMBL1741186 | P51449 | Nuclear receptor ROR-gamma |
130 nM 130 nM 1060 nM 680 nM |
IC50 IC50 IC50 IC50 |
PMID: 24704616
via Super-PRED PMID: 24704616 DOI: 10.1039/C3MD00005B |
| CHEMBL239 | Q07869 | Peroxisome proliferator-activated receptor alpha |
41310 nM |
EC50 |
PMID: 21855333
|
| CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B |
3080 nM 3080 nM 3400 nM 3500 nM 4000 nM 3600 nM 3800 nM 3600 nM 3080 nM 3100 nM 3600 nM 3080 nM 3900 nM 2500 nM 3600 nM 4120 nM 3100 nM 3600 nM 3400 nM 3100 nM 3600 nM 3080 nM 2750 nM |
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: 25907369 PMID: 25559759 PMID: 24953600 PMID: 17125223 PMID: 19846295 PMID: 17489632 PMID: 18707891 PMID: 18798681 PMID: 19008110 PMID: 19362837 PMID: 19632832 PMID: 19782562 PMID: 19836230 PMID: 24224843 PMID: 21555221 PMID: 21571537 PMID: 21680062 PMID: 22940448 PMID: 23022281 PMID: 23141910 PMID: 23387824 |
| CHEMBL3166 | P29350 | Protein-tyrosine phosphatase 1C |
25780 nM |
IC50 |
PMID: 18707891
|
| CHEMBL3521 | P10586 | Receptor-type tyrosine-protein phosphatase F (LAR) |
3800 nM |
IC50 |
PMID: 21453996
|
| CHEMBL1697668 | Q9Y6L6 | Solute carrier organic anion transporter family member 1B1 |
15848.93 nM |
IC50 |
PMID: 23571415
|
| CHEMBL1743121 | Q9NPD5 | Solute carrier organic anion transporter family member 1B3 |
11481.54 nM |
IC50 |
PMID: 23571415
|
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase |
2400 nM 3330 nM |
IC50 IC50 |
PMID: 23387824
PMID: 18707891 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 91.48% | 95.56% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 90.51% | 96.09% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 89.14% | 90.17% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 87.47% | 91.11% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 85.72% | 97.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 85.40% | 98.95% |
| CHEMBL4224 | P49759 | Dual specificty protein kinase CLK1 | 84.53% | 85.30% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 83.38% | 100.00% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 82.97% | 91.19% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 80.12% | 93.00% |
| CHEMBL5028 | O14672 | ADAM10 | 80.08% | 97.50% |
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.