PYRABACTIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H13BrN2O2S
Molecular Weight	377.256
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

BrC1=CC=C(C2=CC=CC=C12)S(=O)(=O)NCC3=CC=CC=N3

InChI

InChIKey=GJSDYQXOSHKOGX-UHFFFAOYSA-N

InChI=1S/C16H13BrN2O2S/c17-15-8-9-16(14-7-2-1-6-13(14)15)22(20,21)19-11-12-5-3-4-10-18-12/h1-10,19H,11H2

HIDE SMILES / InChI

Molecular Formula	C16H13BrN2O2S
Molecular Weight	377.256
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20729862
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/19407142 | https://www.ncbi.nlm.nih.gov/pubmed/20554531

Pyrabactin is a synthetic sulfonamide that functions both as selective ABA receptor agonist and antagonist. Abscisic acid (ABA) is an endogenous small molecule growth inhibitor and regulator of plant stress physiology. Pyrabactin mimics abscisic acid (ABA). It acts through Pyrabactin Resistance 1 (PYR1), the founding member of a family of START proteins called PYR/PYLs, which are necessary for both pyrabactin and ABA signaling in vivo. Pyrabactin an important tool for protecting crops against drought and cold weather.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Functional mechanism of the abscisic acid agonist pyrabactin.	2010-09-10	20554531
Abscisic acid inhibits type 2C protein phosphatases via the PYR/PYL family of START proteins.	2009-05-22	19407142
Chemical genetic interrogation of natural variation uncovers a molecule that is glycoactivated.	2007-11	17891152

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Consistent with the in planta observations, pyrabactin cannot directly inhibit the phosphatase activity of ABI1, but achieves the inhibition through PYL proteins. Further characterization revealed that pyrabactin exhibits an IC50 (1.14 ± 0.07 μm) ∼10-fold higher than that of ABA (93.8 ± 8.4 nm).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:39:03 GMT 2025` Edited by `admin` on `Wed Apr 02 08:39:03 GMT 2025`
Record UNII	L9PM5Q6DDW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRABACTIN

Common Name

English

1-NAPHTHALENESULFONAMIDE, 4-BROMO-N-(2-PYRIDINYLMETHYL)-

Preferred Name

English

4-BROMO-N-(2-PYRIDINYLMETHYL)-1-NAPHTHALENESULFONAMIDE

Systematic Name

English

Code System Code Type Description

CAS

419538-69-5