Compound ID | 3462

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Oleanolic Acid

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: DNA synthesis inhibitor. DNA polymerase inhibitor and membrane-active agent
Target Pathogen: Active against Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium including vancomycin and methicillin resistant strains, and Mycobacterium tuberculosis
Description: Natural product from Salvia officinalis; pentacyclic triterpenoid; shows synergistic activity with isoniazid, rifampicin or ethambutol against Mycobacterium tuberculosis
Year first mentioned: 2007
Development status: Experimental
Chemical structure(s):
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Molecular weight: 456.7
Iso. SMILES: 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 Key: MIJYXULNPSFWEK-GTOFXWBISA-N
Can. SMILES: CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@]43C)O)[C@@H]2C1)C(=O)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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10494
Guide to Pharmacology: oleanolic acid
Citations:
  • https://www.microbiologyresearch.org/content/journal/jmm/10.1099/jmm.0.014837-0
  • https://www.sciencedirect.com/science/article/pii/S096808969900276X
  • https://pmc.ncbi.nlm.nih.gov/articles/PMC4355482/#:~:text=In%20conclusion%2C%20oleanolic%20acid%20has,cytotoxicity%20on%20HEp%2D2%20cells.
  • https://www.jstage.jst.go.jp/article/bpb/30/6/30_6_1147/_article/-char/en

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