:Moronic acid

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 461941059

| ImageFile = moronic acid structure.png

| ImageSize = 200px

| ImageAlt =

| IUPACName = 3-Oxoolean-18-en-28-oic acid

| SystematicName = (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

| OtherNames = Ambronic acid; 3-Oxoolean-18-en-28-oic acid

|Section1={{Chembox Identifiers

| CASNo = 6713-27-5

| CASNo_Ref = {{cascite|changed|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XW8W7HC4JK

| PubChem = 489941

| SMILES = O=C2C([C@@H]1CC[C@@]4([C@@H]([C@@]1(C)CC2)CC[C@@H]5/C3=C/C(C)(C)CC[C@]3(C(=O)O)CC[C@@]45C)C)(C)C

| ChemSpiderID = 429156

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI = 30815

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 472646

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| InChI = 1/C30H46O3/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/h18-19,21-22H,8-17H2,1-7H3,(H,32,33)/t19-,21+,22-,27+,28-,29-,30+/m1/s1

| InChIKey = UMYJVVZWBKIXQQ-QALSDZMNBW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C30H46O3/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/h18-19,21-22H,8-17H2,1-7H3,(H,32,33)/t19-,21+,22-,27+,28-,29-,30+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UMYJVVZWBKIXQQ-QALSDZMNSA-N

}}

|Section2={{Chembox Properties

| C=30 | H=46 | O=3

| Appearance =

| Density =

| MeltingPt =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

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Moronic acid (3-oxoolean-18-en-28-oic acid) is a natural triterpene.{{cite web|title=Comparative Toxicogenomics Database: moronic acid|url=http://ctdbase.org/detail.go?type=chem&acc=C023607}}{{cite journal |pmid=10086989 |year=1999 |last1=Kurokawa |first1=Masahiko |last2=Basnet |first2=Purusotam |last3=Ohsugi |first3=Mizue |last4=Hozumi |first4=Toyoharu |last5=Kadota |first5=Shigetoshi |last6=Namba |first6=Tsuneo |last7=Kawana |first7=Takashi |last8=Shiraki |first8=Kimiyasu |title=Anti-Herpes Simplex Virus Activity of Moronic Acid Purified from Rhus javanica In Vitro and In Vivo |volume=289 |issue=1 |pages=72–8 |journal=The Journal of Pharmacology and Experimental Therapeutics |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10086989}} Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications. The molecule has also been extracted from mistletoe (Phoradendron reichenbachianum).{{cite journal |doi=10.1055/s-2001-15823 |title=Cytotoxic Activity of Moronic Acid and Identification of the New Triterpene 3,4-seco-Olean-18-ene-3,28-dioic Acid from Phoradendron reichenbachianum |year=2001 |last1=Rios |first1=María Yolanda |last2=Salinas |first2=David |last3=Villarreal |first3=María Luisa |journal=Planta Medica |volume=67 |issue=5 |pages=443–6 |pmid=11488459}}

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.{{cite journal |pages=5462–9 |doi=10.1021/jm0601912 |pmc=2512972 |title=Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents |year=2006 |last1=Yu |first1=Donglei |last2=Sakurai |first2=Yojiro |last3=Chen |first3=Chin-Ho |last4=Chang |first4=Fang-Rong |last5=Huang |first5=Li |last6=Kashiwada |first6=Yoshiki |last7=Lee |first7=Kuo-Hsiung |journal=Journal of Medicinal Chemistry |volume=49 |issue=18 |pmid=16942019}} 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.