abscisic acid   

GtoPdb Ligand ID: 10362

Synonyms: (+/-)-(cis,trans)-abscisic acid | (+/-)-Abscisic acid | (RS)-Abscisic acid | ABA
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.
2D Structure
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Physico-chemical Properties
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
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
Classification
Compound class Natural product or derivative
IUPAC Name
(2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-1-cyclohex-2-enyl)-3-methylpenta-2,4-dienoic acid
Synonyms
(+/-)-(cis,trans)-abscisic acid | (+/-)-Abscisic acid | (RS)-Abscisic acid | ABA
Database Links
ChEMBL Ligand CHEMBL379808
GtoPdb PubChem SID 384403642
PubChem CID 5375199
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