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ChEBI
> Main
CHEBI:79060 - icas#12
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ChEBI Name
icas#12
ChEBI ID
CHEBI:79060
Definition
A 4-
O
-(1
H
-indol-3-ylcarbonyl)ascaroside derived from (5
R
)-5-hydroxyhexanoic acid. It is a metabolite of the nematode
Caenorhabditis elegans
.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C21H27NO7
Net Charge
0
Average Mass
405.44160
Monoisotopic Mass
405.17875
InChI
InChI=1S/C21H27NO7/c1-
12(6-
5-
9-
19(24)
25)
27-
21-
17(23)
10-
18(13(2)
28-
21)
29-
20(26)
15-
11-
22-
16-
8-
4-
3-
7-
14(15)
16/h3-
4,7-
8,11-
13,17-
18,21-
23H,5-
6,9-
10H2,1-
2H3,(H,24,25)
/t12-
,13+,17-
,18-
,21-
/m1/s1
InChIKey
AHNZPQNYGMNACV-PNNYZDKCSA-N
SMILES
C[C@H](CCCC(O)=O)O[C@@H]1O[C@@H](C)[C@@H](C[C@H]1O)OC(=O)c1c[nH]c2ccccc12
Metabolite of Species
Details
Caenorhabditis elegans
(NCBI:txid6239)
Detected in wild type (N2) worms. 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):
Caenorhabditis elegans metabolite
A nematode metabolite produced by
Caenorhabditis elegans
.
semiochemical
A molecular messenger released by an organism that affects the behaviour within or between species.
(via
hydroxy fatty acid ascaroside
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
icas#12 (
CHEBI:79060
)
has functional parent
(5
R
)-5-hydroxyhexanoic acid (
CHEBI:78842
)
icas#12 (
CHEBI:79060
)
has functional parent
ascr#12 (
CHEBI:78841
)
icas#12 (
CHEBI:79060
)
has role
Caenorhabditis elegans
metabolite (
CHEBI:78804
)
icas#12 (
CHEBI:79060
)
is a
(ω−1)-hydroxy fatty acid ascaroside (
CHEBI:79205
)
icas#12 (
CHEBI:79060
)
is a
4-
O
-(1
H
-indol-3-ylcarbonyl)ascaroside (
CHEBI:79024
)
icas#12 (
CHEBI:79060
)
is a
monocarboxylic acid (
CHEBI:25384
)
icas#12 (
CHEBI:79060
)
is conjugate acid of
icas#12(1−) (
CHEBI:229462
)
Incoming
icas#12(1−) (
CHEBI:229462
)
is conjugate base of
icas#12 (
CHEBI:79060
)
IUPAC Name
(5
R
)-
5-
{[3,6-
dideoxy-
4-
O
-
(1
H
-
indol-
3-
ylcarbonyl)-
α-
L
-
arabino
-
hexopyranosyl]oxy}hexanoic acid
Synonyms
Sources
5
R
-
(3'
R
-
hydroxy-
5'
R
-
O
-
(1
H
-
indol-
3-
ylcarbonyl)-
6'
S
-
methyl-
(2
H
)-
tetrahydropyran-
2'-
yloxy)-
hexanoic acid
SMID
IC-asc-C6
ChEBI
Manual Xrefs
Databases
icas%2312%0D
SMID
LMFA13040124
LIPID MAPS
View more database links
Registry Numbers
Types
Sources
1355682-92-6
CAS Registry Number
SMID
22233425
Reaxys Registry Number
Reaxys
Citations
Types
Sources
22239548
PubMed citation
Europe PMC
29863473
PubMed citation
Europe PMC
Last Modified
24 January 2024