CHEBI:62460 - helvolic acid

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ChEBI Name helvolic acid
ChEBI ID CHEBI:62460
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C33H44O8
Net Charge 0
Average Mass 568.707
Monoisotopic Mass 568.30362
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
SMILES C=1[C@@]2([C@@]3(CC[C@@]/4([C@@]([C@]3(C([C@H]([C@]2([C@@H](C(C1)=O)C)[H])OC(=O)C)=O)C)(C[C@@H](\C4=C(\CCC=C(C)C)/C(=O)O)OC(=O)C)C)[H])[H])C
Metabolite of Species Details
Aspergillus fumigatus (NCBI:746128) of strain CUGBMF170049 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
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.
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ChEBI Ontology
Outgoing 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 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 Sources
(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 acid IUPAC
(4α,6β,8α,9β,13α,14β,16β,17β)-6,16- bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid ChemIDplus
16-(Acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid ChemIDplus
Fumigacin ChemIDplus
Manual Xrefs Databases
C00023904 KNApSAcK
LMPR0106080005 LIPID MAPS
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Registry Numbers Types Sources
29400-42-8 CAS Registry Number KNApSAcK
29400-42-8 CAS Registry Number ChemIDplus
3230584 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19216560 PubMed citation Europe PMC
27604096 PubMed citation Europe PMC
30070829 PubMed citation Europe PMC
30341897 PubMed citation Europe PMC
30822136 PubMed citation Europe PMC
30972287 PubMed citation Europe PMC
31091673 PubMed citation Europe PMC
31660859 PubMed citation Europe PMC
Last Modified
18 November 2019