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Helvolic acid

Chemical compound From Wikipedia, the free encyclopedia

Helvolic acid is a steroidal antibiotic compound classified as a fusidane-type nortriterpenoid.[2][3] It is a tetracyclic steroid acid characterized by a 29-nordammarane skeleton, which is substituted with acetoxy groups at positions C-6 and C-16, oxo groups at C-3 and C-7, and double bonds at C-1, C-17(20), and C-24. Its molecular formula is C33H44O8.[4]

Quick facts Names, Identifiers ...
Helvolic acid
Names
IUPAC name
(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Other names
Fumigacin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1 X markN
    Key: MDFZYGLOIJNNRM-OAJDADRGSA-N checkY
  • CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
Properties
C33H44O8
Molar mass 568.707 g·mol−1
Appearance crystalline solid
Density 1.2 g/cm³[1]
Boiling point 675.9
slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN (what is checkYX markN ?)
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Natural occurrence

The acid is produced by various fungi, notably Aspergillus species such as Aspergillus fumigatus and Aspergillus terreus, as well as members of the genus Fusarium and Xylaria. The acid was originally isolated from Aspergillus fumigatus.[5]

Helvolic acid was isolated from the culture broth which was separated from the fungus mycelium by filtration.[6]

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