CHEBI:88298 - FR171456

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ChEBI Name FR171456
ChEBI ID CHEBI:88298
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
Supplier Information
Download Molfile XML SDF
Formula C30H44O7
Net Charge 0
Average Mass 516.667
Monoisotopic Mass 516.30870
InChI InChI=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
InChIKey JAHGNOXPMXOEJS-BSPLYONXSA-N
SMILES [C@]123C(C[C@@H]([C@@]([C@@]1(C(C[C@]4([C@]2([C@@H](C[C@]5([C@]4(CC[C@@]5([C@@H](CCC(C(C)C)=C)C)[H])[H])C)O)C3)O)=O)[H])(C)C(O)=O)O)=O
Metabolite of Species Details
Preussia minima (NCBI:txid93984) of strain 15604 See: PubMed
Roles Classification
Biological Role(s): ergosterol biosynthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
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 3beta-hydroxysteroid-4alpha-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.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 acid IUPAC
Citations Waiting for Citations Types Sources
15217189 PubMed citation Europe PMC
15217190 PubMed citation Europe PMC
26456460 PubMed citation Europe PMC
Last Modified
19 December 2017