carlosic acid (CHEBI:133953)

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ChEBI Name	carlosic acid

ChEBI ID	CHEBI:133953

Definition	A tetronic acid derivative that is furan-2(5H)-one which is substituted at positions 3, 4, and 5 by butanoyl, hydroxy, and carboxymethyl groups, respectively (the S enantiomer).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Julian Brandl

Supplier Information

Download	Molfile XML SDF

Formula

C10H12O6

Net Charge

Average Mass

228.199

Monoisotopic Mass

228.06339

InChI

InChI=1S/C10H12O6/c1-2-3-5(11)8-9(14)6(4-7(12)13)16-10(8)15/h6,14H,2-4H2,1H3,(H,12,13)/t6-/m0/s1

InChIKey

FTXHMBAGOBNRPN-LURJTMIESA-N

SMILES

[C@@H]1(C(=C(C(O1)=O)C(CCC)=O)O)CC(O)=O

Metabolite of Species	Details
Aspergillus niger ATCC 1015 (NCBI:txid380704)	See: PubMed
Penicillium charlesii (NCBI:txid69767)	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):	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium.

ChEBI Ontology
Outgoing	carlosic acid (CHEBI:133953) has role Aspergillus metabolite (CHEBI:76956) carlosic acid (CHEBI:133953) has role Penicillium metabolite (CHEBI:76964) carlosic acid (CHEBI:133953) is a butenolide (CHEBI:50523) carlosic acid (CHEBI:133953) is a carboxylic acid (CHEBI:33575) carlosic acid (CHEBI:133953) is a enol (CHEBI:33823) carlosic acid (CHEBI:133953) is a ketone (CHEBI:17087) carlosic acid (CHEBI:133953) is a tetronic acid derivative (CHEBI:63455)

Incoming	carlosic acid methyl ester (CHEBI:133954) has functional parent carlosic acid (CHEBI:133953)

IUPAC Names

[(2S)-4-butanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl]acetic acid

[(2S)-4-butyryl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl]acetic acid

Last Modified

17 November 2016