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CHEBI:65636 - citrafungin B

Default Structure
ChEBI IDCHEBI:65636
ChEBI Namecitrafungin B
Stars
DefinitionA carboxylic ester obtained by the formal condensation of the 4-carboxy group of (2R)-2-hydroxy-2-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-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 Modified5 September 2012
DownloadsMolfile
FormulaC28H38O13
Net Charge0
Average Mass582.599
Monoisotopic Mass582.23124
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\C/C=C\CCCCC)OC1=O
InChIInChI=1S/C28H38O13/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/h6-7,9-10,13-14,18-20,23,39H,2-5,8,11-12,15-17H2,1H3,(H,29,30)(H,32,33)(H,34,35)(H,37,38)/b7-6-,10-9-,14-13+/t18-,19-,20-,23+,28+/m0/s1
InChIKeyBUDVJTLKHWKZFS-PCIDIATHSA-N
Species of MetaboliteComponentSourceComments
Fungi- 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:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
ChEBI Ontology
Outgoing Relation(s)
citrafungin B (CHEBI:65636) has functional parent pentaric acid (CHEBI:25896)
citrafungin B (CHEBI:65636) has role antifungal agent (CHEBI:35718)
citrafungin B (CHEBI:65636) has role EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor (CHEBI:67267)
citrafungin B (CHEBI:65636) has role metabolite (CHEBI:25212)
citrafungin B (CHEBI:65636) is a butan-4-olide (CHEBI:22950)
citrafungin B (CHEBI:65636) is a carboxylic ester (CHEBI:33308)
citrafungin B (CHEBI:65636) 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,8Z)-tetradeca-1,5,8-trien-1-yl]tetrahydrofuran-3-yl}propanoyl]-3,4-dideoxy-L-threo-pentaric acid
Manual XrefsDatabases
9961258ChemSpider
Registry NumbersSources
Reaxys:9681585Reaxys
Citations