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Details

Stereochemistry ACHIRAL
Molecular Formula C7H4O6
Molecular Weight 184.1031
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHELIDONIC ACID

SMILES

OC(=O)C1=CC(=O)C=C(O1)C(O)=O

InChI

InChIKey=PBAYDYUZOSNJGU-UHFFFAOYSA-N
InChI=1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C7H4O6
Molecular Weight 184.1031
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Chelidonic acid (CA) is a γ-pyrone which is contained in the rhizome of Chelidonium majus L. It has multiple pharmacological effects including those of a mild analgesic, an antimicrobial, an oncostatic, a central nervous system sedative and the anti-inflammatory effect. Chelidonic acid evokes antidepressant-like effect through the up-regulation of BDNF in forced swimming test. Chelidonic acid administration significantly increased the mRNA expression of hippocampal estrogen receptor-β. The levels of hippocampal interleukin (IL)-1β, IL-6, and tumor necrosis factor-α were effectively attenuated by the administration of chelidonic acid. In addition, chelidonic acid significantly increased the levels of 5-hydroxytryptamine (serotonin), dopamine, and norepinephrine compared with those levels for the mice that were administered distilled water in the hippocampus. Chelidonic acid might serve as a new therapeutic strategy for the regulation of depression associated with inflammation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.2 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Tracer studies with 13C-labeled carbohydrates in cultured plant cells. Retrobiosynthetic analysis of chelidonic acid biosynthesis.
2001 May
Cationic, neutral and anionic metal(II) complexes derived from 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid).
2007 May
Effect of mucilage from yam on activation of lymphocytic immune cells.
2007 Summer
Patents

Sample Use Guides

Rats: In mast cell degranulation studies, ovalbumin immunized and challenged rats, chelidonic acid (1, 3 and 10mg/kg, i.p.) dose relatedly prevented ovalbumin challenge induced mast cell degranulation by differing degrees when compared with the vehicle-treated group, and these effects were comparable with prednisolone (10mg/kg).
Route of Administration: Intraperitoneal
GAD was preincubated for 30 min with 1 mM chelidonic acid (CA), 5 mM glutamate (GLU), and 5 mM glutamate + 1 mM chelidonic acid (GLU + CA). Kinetic analysis showed that chelidonic acid was competitive with glutamate with a K; of 1.2 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:50:29 GMT 2023
Edited
by admin
on Fri Dec 15 18:50:29 GMT 2023
Record UNII
T33U4W5K6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHELIDONIC ACID
MI  
Common Name English
JERVASIC ACID
Common Name English
NSC-3979
Code English
4-OXO-4H-PYRAN-2,6-DICARBOXYLIC ACID
Systematic Name English
CHELIDONIC ACID [MI]
Common Name English
.GAMMA.-PYRONE-2,6-DICARBOXYLIC ACID
Common Name English
JERVA ACID
Common Name English
JERVAIC ACID
Common Name English
4H-PYRAN-2,6-DICARBOXYLIC ACID, 4-OXO-
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
202-749-0
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
WIKIPEDIA
Chelidonic acid
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
FDA UNII
T33U4W5K6O
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID30243928
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
CAS
99-32-1
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
MESH
C046884
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
NSC
3979
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
PUBCHEM
7431
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY
MERCK INDEX
m3321
Created by admin on Fri Dec 15 18:50:29 GMT 2023 , Edited by admin on Fri Dec 15 18:50:29 GMT 2023
PRIMARY Merck Index
Related Record Type Details
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