Chemistry:Moronic acid
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| Names | |
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| IUPAC name
3-Oxoolean-18-en-28-oic acid
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| Systematic IUPAC name
(4aS,6aR,6bR,8aR,12aR,12bR,14aS)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-octadecahydropicene-4a(2H)-carboxylic acid | |
| Other names
Ambronic acid; 3-Oxoolean-18-en-28-oic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C30H46O3 | |
| Molar mass | 454.695 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Moronic acid (3-oxoolean-18-en-28-oic acid) is a natural triterpene.[1][2] Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications.[2] The molecule has also been extracted from mistletoe (Phoradendron reichenbachianum).[3]
Bevirimat, a derivative of the related triterpenoid betulinic acid, is under development as an anti-HIV drug; however, moronic acid has shown better antiviral profiles in vitro than bevirimat.[4] A particular moronic acid derivative showed potent anti-HIV activity with EC50 values of 0.0085 μM against NL4-3, 0.021 μM against PI-R (a multiple protease inhibitor resistant strain), and 0.13 μM against FHR-2 (an HIV strain resistant to (bevirimat). This derivative has become a new lead for clinical trials and is also active against herpes simplex virus 1.[4]
References
- ↑ "Comparative Toxicogenomics Database: moronic acid". http://ctdbase.org/detail.go?type=chem&acc=C023607.
- ↑ 2.0 2.1 Kurokawa, Masahiko; Basnet, Purusotam; Ohsugi, Mizue; Hozumi, Toyoharu; Kadota, Shigetoshi; Namba, Tsuneo; Kawana, Takashi; Shiraki, Kimiyasu (1999). "Anti-Herpes Simplex Virus Activity of Moronic Acid Purified from Rhus javanica In Vitro and In Vivo". The Journal of Pharmacology and Experimental Therapeutics 289 (1): 72–8. PMID 10086989. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10086989.
- ↑ Rios, María Yolanda; Salinas, David; Villarreal, María Luisa (2001). "Cytotoxic Activity of Moronic Acid and Identification of the New Triterpene 3,4-seco-Olean-18-ene-3,28-dioic Acid from Phoradendron reichenbachianum". Planta Medica 67 (5): 443–6. doi:10.1055/s-2001-15823. PMID 11488459.
- ↑ 4.0 4.1 Yu, Donglei; Sakurai, Yojiro; Chen, Chin-Ho; Chang, Fang-Rong; Huang, Li; Kashiwada, Yoshiki; Lee, Kuo-Hsiung (2006). "Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents". Journal of Medicinal Chemistry 49 (18): 5462–9. doi:10.1021/jm0601912. PMID 16942019.
External links
- CTD's Moronic acid page from the Comparative Toxicogenomics Database
- NLM/NIH Medical Subject Heading
- KEGG Terpenoid Synthesis Pathway
- Molecules with silly names
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