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> Main
CHEBI:78695 - cantharidic acid
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ChEBI Name
cantharidic acid
ChEBI ID
CHEBI:78695
Definition
A monoterpenoid with an epoxy-bridged bicyclic dicarboxylic acid structure, which acts as an inhibitor of protein phosphatases 1 and 2A.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C10H14O5
Net Charge
0
Average Mass
214.21520
Monoisotopic Mass
214.08412
InChI
InChI=1S/C10H14O5/c1-
9(7(11)
12)
5-
3-
4-
6(15-
5)
10(9,2)
8(13)
14/h5-
6H,3-
4H2,1-
2H3,(H,11,12)
(H,13,14)
/t5-
,6+,9+,10-
InChIKey
NMTNUQBORQILRK-XCVPVQRUSA-N
SMILES
C[C@@]1([C@@H]2CC[C@@H](O2)[C@@]1(C)C(O)=O)C(O)=O
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):
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor
Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
cantharidic acid (
CHEBI:78695
)
has functional parent
cantharidin (
CHEBI:64213
)
cantharidic acid (
CHEBI:78695
)
has role
apoptosis inducer (
CHEBI:68495
)
cantharidic acid (
CHEBI:78695
)
has role
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (
CHEBI:37153
)
cantharidic acid (
CHEBI:78695
)
has role
hepatotoxic agent (
CHEBI:50908
)
cantharidic acid (
CHEBI:78695
)
is a
bridged compound (
CHEBI:35990
)
cantharidic acid (
CHEBI:78695
)
is a
dicarboxylic acid (
CHEBI:35692
)
cantharidic acid (
CHEBI:78695
)
is a
monoterpenoid (
CHEBI:25409
)
cantharidic acid (
CHEBI:78695
)
is a
oxabicycloalkane (
CHEBI:46733
)
IUPAC Name
(1
R
,2
S
,3
R
,4
S
)-
2,3-
dimethyl-
7-
oxabicyclo[2.2.1]heptane-
2,3-
dicarboxylic acid
Manual Xrefs
Databases
Cantharidic_acid
Wikipedia
WO2011056222
Patent
View more database links
Registry Numbers
Types
Sources
17311
Reaxys Registry Number
Reaxys
28874-45-5
CAS Registry Number
ChemIDplus
Citations
Types
Sources
10403630
PubMed citation
Europe PMC
10900240
PubMed citation
Europe PMC
22210093
PubMed citation
Europe PMC
22337773
PubMed citation
Europe PMC
2955551
PubMed citation
Europe PMC
Last Modified
03 June 2014