EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:88298 - FR171456

ChEBI IDCHEBI:88298
ChEBI NameFR171456
Stars
DefinitionA steroid acid that is 9β,19-cyclo-5α-ergost-24(28)-ene-4α-carboxylic acid which is substituted by hydroxy groups at the 3β, 8α, and 11α positions, by a methyl group at the 4β position, and by oxo groups at positions 1 and 6. It is a cholesterol and ergosterol synthesis inhibitor isolated from the fungus Sporormiella minima that specifically targets the enzyme, sterol-4-alpha-carboxylate-3-dehydrogenase, encoded by ERG26 in budding yeast, and NSDHL in humans.
Last Modified19 December 2017
Submitterrnash
DownloadsMolfile
FormulaC30H44O7
Net Charge0
Average Mass516.675
Monoisotopic Mass516.30870
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CCC(=C)C(C)C)[C@@]1(C)C[C@@H](O)[C@@]13C[C@@]14C(=O)C[C@H](O)[C@@](C)(C(=O)O)[C@]4([H])C(=O)C[C@]23O
InChIInChI=1S/C30H44O7/c1-15(2)16(3)7-8-17(4)18-9-10-20-26(18,5)13-23(34)29-14-28(29)22(33)11-21(32)27(6,25(35)36)24(28)19(31)12-30(20,29)37/h15,17-18,20-21,23-24,32,34,37H,3,7-14H2,1-2,4-6H3,(H,35,36)/t17-,18-,20-,21+,23-,24+,26-,27-,28+,29+,30+/m1/s1
InChIKeyJAHGNOXPMXOEJS-BSPLYONXSA-N
Species of MetaboliteComponentSourceComments
Preussia minima (ncbitaxon:93984) - PubMed (15217189) Strain: 15604
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
EC 1.1.1.170 [3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating)] inhibitor  An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 3β-hydroxysteroid-4α-carboxylate 3-dehydrogenase (decarboxylating) (EC 1.1.1.170).
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ergosterol biosynthesis inhibitor  Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
ChEBI Ontology
Outgoing Relation(s)
FR171456 (CHEBI:88298) has role antifungal agent (CHEBI:35718)
FR171456 (CHEBI:88298) has role EC 1.1.1.170 [3β-hydroxysteroid-4α-carboxylate 3-dehydrogenase (decarboxylating)] inhibitor (CHEBI:90113)
FR171456 (CHEBI:88298) has role ergosterol biosynthesis inhibitor (CHEBI:75282)
FR171456 (CHEBI:88298) has role fungal metabolite (CHEBI:76946)
FR171456 (CHEBI:88298) is a 11α-hydroxy steroid (CHEBI:19129)
FR171456 (CHEBI:88298) is a 3β-hydroxy steroid (CHEBI:36836)
FR171456 (CHEBI:88298) is a 6-oxo steroid (CHEBI:36883)
FR171456 (CHEBI:88298) is a 8-hydroxy steroid (CHEBI:139333)
FR171456 (CHEBI:88298) is a cyclopropanes (CHEBI:51454)
FR171456 (CHEBI:88298) is a steroid acid (CHEBI:47891)
IUPAC Name 
3β,8α,11α-trihydroxy-4-methyl-1,6-dioxo-9β,19-cyclo-5α-ergost-24(28)-ene-4α-carboxylic acid
Synonym  Source
(3β,4α,5α,8α,9β,11α)-3,8,11-trihydroxy-4-methyl-1,6-dioxo-9,19-cycloergost-24(28)-ene-4-carboxylic acidIUPAC
Citations