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> Main
CHEBI:133953 - carlosic acid
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ChEBI Name
carlosic acid
ChEBI ID
CHEBI:133953
Definition
A tetronic acid derivative that is furan-2(5
H
)-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
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Formula
C10H12O6
Net Charge
0
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 (Br
o
nsted 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
.
View more via ChEBI Ontology
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
[(2
S
)-4-butanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl]acetic acid
[(2
S
)-4-butyryl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl]acetic acid
Synonyms
Sources
(−)-carlosic acid
ChEBI
(
S
)-carlosic acid
ChemIDplus
Manual Xrefs
Databases
34485443
ChemSpider
54687841
PubChem
View more database links
Registry Numbers
Types
Sources
33404-61-4
CAS Registry Number
ChemIDplus
3614683
Reaxys Registry Number
Reaxys
Citations
Types
Sources
13867384
PubMed citation
Europe PMC
16745739
PubMed citation
Europe PMC
19847338
PubMed citation
Europe PMC
25044953
PubMed citation
Europe PMC
Last Modified
17 November 2016