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ChEBI
> Main
CHEBI:65637 - citrifolinoside
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ChEBI Ontology
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ChEBI Name
citrifolinoside
ChEBI ID
CHEBI:65637
Definition
An unusual iridoid monoterpenoid isolated from the leaves of
Morinda citrifolia
. It exhibits significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures.
Stars
This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Molfile
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Molfile
Formula
C28H30O15
Net Charge
0
Average Mass
606.52880
Monoisotopic Mass
606.15847
InChI
InChI=1S/C28H30O15/c1-
36-
14-
5-
4-
10(6-
13(14)
30)
18(31)
11-
7-
28(43-
25(11)
35)
17-
16(21-
23(28)
41-
21)
12(24(34)
38-
3)
9-
39-
26(17)
42-
27-
22(37-
2)
20(33)
19(32)
15(8-
29)
40-
27/h4-
7,9,15-
17,19-
23,26-
27,29-
30,32-
33H,8H2,1-
3H3/t15-
,16-
,17-
,19-
,20+,21+,22-
,23+,26+,27+,28-
/m1/s1
InChIKey
NUMSWUCLFNXPFE-WVQLPIEPSA-N
SMILES
CO[C@H]
1[C@H]
(O[C@@H]
2OC=C([C@H]
3[C@@H]
4O[C@@H]
4[C@]
4(OC(=O)
C(=C4)
C(=O)
c4ccc(OC)
c(O)
c4)
[C@@H]
23)
C(=O)
OC)
O[C@H]
(CO)
[C@@H]
(O)
[C@@H]
1O
Metabolite of Species
Details
Morinda citrifolia
(NCBI:txid43522)
Found in leaf
(BTO:0000713)
. See:
PubMed
Roles Classification
Biological Role
(s):
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
AP-1 antagonist
An antogonist that interferes with the action of activator protein 1 (AP-1).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
citrifolinoside (
CHEBI:65637
)
has role
AP-1 antagonist (
CHEBI:67199
)
citrifolinoside (
CHEBI:65637
)
has role
metabolite (
CHEBI:25212
)
citrifolinoside (
CHEBI:65637
)
is a
β-
D
-glucoside (
CHEBI:22798
)
citrifolinoside (
CHEBI:65637
)
is a
γ-lactone (
CHEBI:37581
)
citrifolinoside (
CHEBI:65637
)
is a
aromatic ether (
CHEBI:35618
)
citrifolinoside (
CHEBI:65637
)
is a
aromatic ketone (
CHEBI:76224
)
citrifolinoside (
CHEBI:65637
)
is a
enone (
CHEBI:51689
)
citrifolinoside (
CHEBI:65637
)
is a
epoxide (
CHEBI:32955
)
citrifolinoside (
CHEBI:65637
)
is a
iridoid monoterpenoid (
CHEBI:50563
)
citrifolinoside (
CHEBI:65637
)
is a
methyl ester (
CHEBI:25248
)
citrifolinoside (
CHEBI:65637
)
is a
oxaspiro compound (
CHEBI:37948
)
citrifolinoside (
CHEBI:65637
)
is a
phenols (
CHEBI:33853
)
IUPAC Name
methyl (1a'
S
,1b'
S
,2
R
,5'
S
,5a'
S
,6a'
S
)-
5'-
(β-
D
-
glucopyranosyloxy)-
4-
(3-
hydroxy-
4-
methoxybenzoyl)-
5-
oxo-
1a',5',5a',6a'-
tetrahydro-
1b'
H
,5
H
-
spiro[furan-
2,6'-
oxireno[3,4]cyclopenta[1,2-
c
]pyran]-
2'-
carboxylate
Citations
Types
Sources
11348221
PubMed citation
Europe PMC
17078712
PubMed citation
Europe PMC
Last Modified
16 March 2015
General Comment
2012-12-12
Citrifolinoside and yopaaoside A were found to be identical, and their structures were revised as shown:
Org Lett.
2006, 8(23), 5337-40.