CHEBI:65636 - citrafungin B

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ChEBI Name citrafungin B
ChEBI ID CHEBI:65636
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H38O13
Net Charge 0
Average Mass 582.59350
Monoisotopic Mass 582.23124
InChI InChI=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
InChIKey BUDVJTLKHWKZFS-PCIDIATHSA-N
SMILES [H][C@@]1(C[C@@H](OC1=O)\C=C\CC\C=C/C\C=C/CCCCC)[C@](O)(CC(=O)O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O)C(O)=O
Metabolite of Species Details
Fungi Sterile mycelium of strain MF6339 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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
9961258 ChemSpider
View more database links
Registry Number Type Source
9681585 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
14748587 PubMed citation Europe PMC
Last Modified
05 September 2012