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CHEBI:62460 - helvolic acid

ChEBI IDCHEBI:62460
ChEBI Namehelvolic acid
Stars
DefinitionA steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.
Last Modified22 August 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC33H44O8
Net Charge0
Average Mass568.707
Monoisotopic Mass568.30362
SMILES[H][C@]12[C@H](C)C(=O)C=C[C@]1(C)[C@]1([H])CC[C@@]3([H])/C(=C(\CCC=C(C)C)C(=O)O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]1(C)C(=O)[C@H]2OC(C)=O
InChIInChI=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
InChIKeyMDFZYGLOIJNNRM-OAJDADRGSA-N
Species of MetaboliteComponentSourceComments
Aspergillus fumigatus (ncbitaxon:746128) - PubMed (19216560) Strain: CUGBMF170049
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
mycotoxin  Poisonous substance produced by fungi.
ChEBI Ontology
Outgoing Relation(s)
helvolic acid (CHEBI:62460) has parent hydride dammarane (CHEBI:36488)
helvolic acid (CHEBI:62460) has role antibacterial agent (CHEBI:33282)
helvolic acid (CHEBI:62460) has role fungal metabolite (CHEBI:76946)
helvolic acid (CHEBI:62460) has role mycotoxin (CHEBI:25442)
helvolic acid (CHEBI:62460) is a 3-oxo-Δ1 steroid (CHEBI:20156)
helvolic acid (CHEBI:62460) is a acetate ester (CHEBI:47622)
helvolic acid (CHEBI:62460) is a monocarboxylic acid (CHEBI:25384)
helvolic acid (CHEBI:62460) is a steroid acid (CHEBI:47891)
helvolic acid (CHEBI:62460) is conjugate acid of helvolate (CHEBI:62461)
Incoming Relation(s)
helvolic acid methyl ester (CHEBI:141360) has functional parent helvolic acid (CHEBI:62460)
helvolate (CHEBI:62461) is conjugate base of helvolic acid (CHEBI:62460)
IUPAC Name 
(17Z)-6β,16β-diacetoxy-4α,8,14-trimethyl-3,7-dioxo-5α,8α,9β,13α,14β-18-norcholesta-1,17,24-trien-21-oic acid
Synonyms  Source
FumigacinChemIDplus
(2Z)-2-[(4α,5α,6β,8α,9β,13α,14β,16β,17Z)-6,16-diacetoxy-4,8,10,14-tetramethyl-3,7-dioxogon-1-en-17-ylidene]-6-methylhept-5-enoic acidIUPAC
(4α,6β,8α,9β,13α,14β,16β,17β)-6,16- bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acidChemIDplus
16-(Acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acidChemIDplus
Manual XrefsDatabases
LMPR0106080005LIPID MAPS
C00023904KNApSAcK
Registry NumbersSources
Beilstein:3230584Beilstein
CAS:29400-42-8ChemIDplus
CAS:29400-42-8KNApSAcK
Citations