Helvolic acid, Mycotoxin

Key facts

CAS number

29400-42-8

Purity

>96%

Form

Solid

form

Source

Aspergillus fumigatus

Molecular weight

568.7 Da

Molecular formula

C₃₃H₄₄O₈

PubChem

3002143

Nature

Native

Solubility

Soluble in DMSO

Biochemical name

Helvolic acid

Biological description

Mycotoxin. Broad spectrum antibiotic agent. Weakly inhibits GTPase. Active against Gram positive and negative bacteria. Inhibits protein biosynthesis via EF-2. Shows antioxidant effects.

Canonical smiles

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

Isomeric smiles

C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)OC(=O)C

InChi

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

InChiKey

MDFZYGLOIJNNRM-OAJDADRGSA-N

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