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> Main
CHEBI:90272 - lactucin 15-oxalate
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ChEBI Ontology
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ChEBI Name
lactucin 15-oxalate
ChEBI ID
CHEBI:90272
Definition
A sesquiterpene lactone obtained by formal condensation of one of the carboxy groups of oxalic acid with the 15-hydroxy group of lactucin. Found in chicory.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C17H16O8
Net Charge
0
Average Mass
348.305
Monoisotopic Mass
348.08452
InChI
InChI=1S/C17H16O8/c1-
6-
3-
9(18)
12-
7(2)
16(22)
25-
14(12)
13-
8(4-
10(19)
11(6)
13)
5-
24-
17(23)
15(20)
21/h4,9,12-
14,18H,2-
3,5H2,1H3,(H,20,21)
/t9-
,12+,13-
,14-
/m0/s1
InChIKey
LMOXWYJMYLUOMS-VZLIPTOUSA-N
SMILES
O=C(O)C(=O)OCC1=CC(=O)C=2[C@]1([C@]3(OC(=O)C(=C)[C@@]3([C@@H](O)CC2C)[H])[H])[H]
Metabolite of Species
Details
Cichorium intybus
(NCBI:txid13427)
See:
MetaboLights Study
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):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
lactucin 15-oxalate (
CHEBI:90272
)
has functional parent
lactucin (
CHEBI:6358
)
lactucin 15-oxalate (
CHEBI:90272
)
has functional parent
oxalic acid (
CHEBI:16995
)
lactucin 15-oxalate (
CHEBI:90272
)
has role
plant metabolite (
CHEBI:76924
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
azulenofuran (
CHEBI:39433
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
cyclic terpene ketone (
CHEBI:36130
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
enone (
CHEBI:51689
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
oxo monocarboxylic acid (
CHEBI:35871
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
secondary alcohol (
CHEBI:35681
)
lactucin 15-oxalate (
CHEBI:90272
)
is a
sesquiterpene lactone (
CHEBI:37667
)
IUPAC Name
{[(3a
R
,4
S
,9a
S
,9b
R
)-
4-
hydroxy-
6-
methyl-
3-
methylidene-
2,7-
dioxo-
2,3,3a,4,5,7,9a,9b-
octahydroazuleno[4,5-
b
]furan-
9-
yl]methoxy}(oxo)acetic acid
Manual Xref
Database
C00034017
KNApSAcK
View more database links
Registry Number
Type
Source
303130-76-9
CAS Registry Number
KNApSAcK
Last Modified
15 June 2016