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CHEBI:65635 - citrafungin A

ChEBI IDCHEBI:65635
ChEBI Namecitrafungin A
Stars
DefinitionA carboxylic ester obtained by the formal condensation of 4-carboxy group of (2R)-2-hydroxy-2-{(3R,5R)-2-oxo-5-[(1E,5Z)-tetradeca-1,5-dien-1-yl]tetrahydrofuran-3-yl}butanedioic acid with the hydroxy group of 3-carboxy-2,3-dideoxy-L-threo-pentaric acid. It is a fungal metabolite that acts as an inhibitor of geranylgeranyltransferase type I(GGTase I) of pathogenic fungal species.
Last Modified8 November 2024
DownloadsMolfile
FormulaC28H40O13
Net Charge0
Average Mass584.615
Monoisotopic Mass584.24689
SMILES[H][C@]1([C@](O)(CC(=O)O[C@@H](C(=O)O)[C@H](CC(=O)O)C(=O)O)C(=O)O)C[C@H](/C=C/CC/C=C\CCCCCCCC)OC1=O
InChIInChI=1S/C28H40O13/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-20(26(36)40-18)28(39,27(37)38)17-22(31)41-23(25(34)35)19(24(32)33)16-21(29)30/h9-10,13-14,18-20,23,39H,2-8,11-12,15-17H2,1H3,(H,29,30)(H,32,33)(H,34,35)(H,37,38)/b10-9-,14-13+/t18-,19-,20-,23+,28+/m0/s1
InChIKeyILSZYBVYZFASML-KRZMJZBHSA-N
Species of MetaboliteComponentSourceComments
Fungi (ncbitaxon:4751) - PubMed (14748587) Sterile mycelium Strain: MF6339
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein geranylgeranyltransferase type I (EC 2.5.1.59).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
citrafungin A (CHEBI:65635) has functional parent pentaric acid (CHEBI:25896)
citrafungin A (CHEBI:65635) has role antifungal agent (CHEBI:35718)
citrafungin A (CHEBI:65635) has role EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor (CHEBI:67267)
citrafungin A (CHEBI:65635) has role metabolite (CHEBI:25212)
citrafungin A (CHEBI:65635) is a butan-4-olide (CHEBI:22950)
citrafungin A (CHEBI:65635) is a carboxylic ester (CHEBI:33308)
citrafungin A (CHEBI:65635) is a tetracarboxylic acid (CHEBI:35742)
IUPAC Name 
3-carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-3-{(3R,5R)-2-oxo-5-[(1E,5Z)-tetradeca-1,5-dien-1-yl]tetrahydrofuran-3-yl}propanoyl]-3,4-dideoxy-L-threo-pentaric acid
Manual XrefsDatabases
9585549ChemSpider
Registry NumbersSources
Reaxys:9682030Reaxys
Citations