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Details

Stereochemistry RACEMIC
Molecular Formula C18H18ClN3O
Molecular Weight 327.808
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRASSINAZOLE

SMILES

CC(O)(C(CC1=CC=C(Cl)C=C1)N2C=NC=N2)C3=CC=CC=C3

InChI

InChIKey=YULDTPKHZNKFEY-UHFFFAOYSA-N
InChI=1S/C18H18ClN3O/c1-18(23,15-5-3-2-4-6-15)17(22-13-20-12-21-22)11-14-7-9-16(19)10-8-14/h2-10,12-13,17,23H,11H2,1H3

HIDE SMILES / InChI

Molecular Formula C18H18ClN3O
Molecular Weight 327.808
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/25793645

Brassinazole is a synthetic triazole-type inhibitor of the biosynthesis of plant hormones brassinosteroids (BR) that play critical roles in regulating broad aspects of plant growth and development. The structure of brassinazole is similar to pacrobutrazol, a gibberellin biosynthesis inhibitor. Brassinazole has displayed the ability to induce morphological changes in dark-grown Arabidopsis. Additional experiments show that Brassinazole inhibition of plant growth can be prevented by co-application of BR. Brassinazole is a specific inhibitor of C-22 hydroxylase (CYP90B1) in BR biosynthesis, and the application use of brassinazole has emerged as an effective way of complementing BR-deficient mutants to elucidate the functions of BRs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.05 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Characterization of brassinazole, a triazole-type brassinosteroid biosynthesis inhibitor.
2000 May
Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta.
2001 Jul 13
YCZ-18 is a new brassinosteroid biosynthesis inhibitor.
2015
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
A. thaliana (ecotype Colombia) seedlings were grown in a liquid culture of 0.5× Murashige and Skoog salt medium plus 1.5% sucrose for 7 days in continuous light. Brassinazole or brassinolide was added to final concentrations of 3 μM or 30 nM (0.01% final Me2SO concentration), respectively, and seedlings were incubated for 3 h.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:49:31 GMT 2023
Edited
by admin
on Sat Dec 16 11:49:31 GMT 2023
Record UNII
N9XRW3TF90
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRASSINAZOLE
Common Name English
1H-1,2,4-TRIAZOLE-1-ETHANOL, .BETA.-((4-CHLOROPHENYL)METHYL)-.ALPHA.-METHYL-.ALPHA.-PHENYL-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID1043708
Created by admin on Sat Dec 16 11:49:31 GMT 2023 , Edited by admin on Sat Dec 16 11:49:31 GMT 2023
PRIMARY
FDA UNII
N9XRW3TF90
Created by admin on Sat Dec 16 11:49:31 GMT 2023 , Edited by admin on Sat Dec 16 11:49:31 GMT 2023
PRIMARY
CAS
280129-83-1
Created by admin on Sat Dec 16 11:49:31 GMT 2023 , Edited by admin on Sat Dec 16 11:49:31 GMT 2023
ALTERNATIVE
CAS
224047-41-0
Created by admin on Sat Dec 16 11:49:31 GMT 2023 , Edited by admin on Sat Dec 16 11:49:31 GMT 2023
PRIMARY
PUBCHEM
15477807
Created by admin on Sat Dec 16 11:49:31 GMT 2023 , Edited by admin on Sat Dec 16 11:49:31 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY