Moronic acid

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Moronic acid
Moronic acid structure.png
Names
IUPAC name
(4aS,6aR,6aS,6bR,8aS,12aS,14aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-4,5,6,6a,7,8,8a,11,12,13,14,14a-dodecahydro-3H-picene-4a-carboxylic acid
Other names
Ambronic acid; 3-Oxoolean-18-en-28-oic acid
Identifiers
6713-27-5 N
ChEBI CHEBI:30815 YesY
ChEMBL ChEMBL472646 YesY
ChemSpider 429156 YesY
Jmol 3D model Interactive image
PubChem 489941
  • InChI=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 YesY
    Key: UMYJVVZWBKIXQQ-QALSDZMNSA-N YesY
  • 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
    Key: UMYJVVZWBKIXQQ-QALSDZMNBW
  • 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
Properties
C30H46O3
Molar mass 454.70 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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  2. 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.

External links