abscisic acid   Click here for help

GtoPdb Ligand ID: 10362

Synonyms: (+/-)-(cis,trans)-abscisic acid | (+/-)-Abscisic acid | (RS)-Abscisic acid | ABA
Immunopharmacology Ligand
Comment: We show the compound without specified stereochemistry to represent racemic abscisic acid. The (1S)- or (+)-enantiomer (PubChem CID 12305886), is the naturally occurring and more active form of abscisic acid.
Abscisic acid activates human granulocytes [3] and stimulates insulin secretion by human and murine pancreatic β cells [1], via similar signalling pathways, that require a LANCL2-containing protein complex linked to a Gi protein, that ultimately leads to elevation of the intracellular Ca2+ concentration [7]. In cellular and animal models abscisic acid exerts anti-inflammatory [3-5] and antidiabetic [2,6] effects.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 74.6
Molecular weight 264.14
XLogP 0.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C=C(C=CC1(O)C(=CC(=O)CC1(C)C)C)C
Isomeric SMILES OC(=O)/C=C(\C=C\C1(O)C(=CC(=O)CC1(C)C)C)/C
InChI InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-
InChI Key JLIDBLDQVAYHNE-LXGGSRJLSA-N
References
1. Bruzzone S, Bodrato N, Usai C, Guida L, Moreschi I, Nano R, Antonioli B, Fruscione F, Magnone M, Scarfì S et al.. (2008)
Abscisic acid is an endogenous stimulator of insulin release from human pancreatic islets with cyclic ADP ribose as second messenger.
J Biol Chem, 283 (47): 32188-97. [PMID:18784081]
2. Bruzzone S, Magnone M, Mannino E, Sociali G, Sturla L, Fresia C, Booz V, Emionite L, De Flora A, Zocchi E. (2015)
Abscisic Acid Stimulates Glucagon-Like Peptide-1 Secretion from L-Cells and Its Oral Administration Increases Plasma Glucagon-Like Peptide-1 Levels in Rats.
PLoS ONE, 10 (10): e0140588. [PMID:26488296]
3. Bruzzone S, Moreschi I, Usai C, Guida L, Damonte G, Salis A, Scarfì S, Millo E, De Flora A, Zocchi E. (2007)
Abscisic acid is an endogenous cytokine in human granulocytes with cyclic ADP-ribose as second messenger.
Proc Natl Acad Sci USA, 104 (14): 5759-64. [PMID:17389374]
4. Guri AJ, Evans NP, Hontecillas R, Bassaganya-Riera J. (2011)
T cell PPARγ is required for the anti-inflammatory efficacy of abscisic acid against experimental IBD.
J Nutr Biochem, 22 (9): 812-9. [PMID:21109419]
5. Guri AJ, Hontecillas R, Bassaganya-Riera J. (2010)
Abscisic acid ameliorates experimental IBD by downregulating cellular adhesion molecule expression and suppressing immune cell infiltration.
Clin Nutr, 29 (6): 824-31. [PMID:20236740]
6. Guri AJ, Hontecillas R, Si H, Liu D, Bassaganya-Riera J. (2007)
Dietary abscisic acid ameliorates glucose tolerance and obesity-related inflammation in db/db mice fed high-fat diets.
Clin Nutr, 26 (1): 107-16. [PMID:17000034]
7. Sturla L, Fresia C, Guida L, Bruzzone S, Scarfì S, Usai C, Fruscione F, Magnone M, Millo E, Basile G et al.. (2009)
LANCL2 is necessary for abscisic acid binding and signaling in human granulocytes and in rat insulinoma cells.
J Biol Chem, 284 (41): 28045-57. [PMID:19667068]