4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid
Basic information
- CAS
188011-69-0- Standard SMILES
O=C(O)CCC(=O)Nc1ccc(Br)cn1- InChIKey
XFYYQDHEDOXWGA-UHFFFAOYSA-N- Molecular formula
- C9H9BrN2O3
- Average molar mass
- 273.08 g/mol
- Monoisotopic mass
- 271.97965
Names & identifiers
- Preferred name
- 4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid
- IUPAC
- 4-[(5-bromo-2-pyridinyl)amino]-4-oxobutanoic acid
- English name
- Bikinin
- Molecular formula
- C9H9BrN2O3
- Molecular weight
- 273.08
Names & synonyms
4-((5-Bromopyridin-2-yl)amino)-4-oxobutanoic acid4-[(5-bromopyridin-2-yl)amino]-4-oxobutanoic acid4-[(5-bromo-2-pyridinyl)amino]-4-oxobutanoic acid3-[(5-bromopyridin-2-yl)carbamoyl]propanoic acid3-((5-bromopyridin-2-yl)carbamoyl)propanoic acid4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid4-((5-bromopyridin-1-ium-2-yl)amino)-4-oxobutanoate4-[(5-bromopyridin-1-ium-2-yl)amino]-4-oxobutanoateRefChem:509628694-754-3Bikinin188011-69-0
Show more names
CS-1658Bikinin, >98%Bikinin(Abrasin)Bikinin USP/EP/BPBikinin, 10 mM in DMSOBikinin - CAS 188011-69-0 - CalbiochemBikinin, 7 Arabidopsis GSK-3 inhibitor4-[(5-Bromo-2-pyridyl)amino]-4-oxobutyric Acid
AbrasinN-(5-Bromo-pyridin-2-yl)-succinamic acidn-(5-bromopyridin-2-yl)succinamic acidMFCD00116442IFLab1_000935HMS2304N164-(5-bromopyridin-2-ylamino)-4-oxobutanoic acid4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoic acid
Database identifiers
- CAS
188011-69-0- PubChem CID
- 647833
- DTXSID
DTXSID20349448- ChEMBL
CHEMBL1236104- EC Number
- 694-754-3
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 79.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 248
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 144 °C · 144°C(lit.)
- Boiling point
- 521.6 · 521.6±45.0 °C(Predicted)
- Density
- 1.711 · 1.711
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · DMSO: ≥5mg/mL
- form
- White solid
- pka
- 4.59 · 4.59±0.10(Predicted)
- color
- white to tan
- Major Application
- agriculture
- InChI
- 1S/C9H9BrN2O3/c10-6-1-2-7(11-5-6)12-8(13)3-4-9(14)15/h1-2,5H,3-4H2,(H,14,15)(H,11,12,13)
- InChIKey
- XFYYQDHEDOXWGA-UHFFFAOYSA-N
- SMILES
- OC(=O)CCC(=O)Nc1ccc(Br)cn1
- CAS DataBase Reference
- 188011 · 188011-69-0
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 67 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (98.5%)
Safety data
- wgk
- 3
- hs_code
- 2933.39.9200
- risk_code
- 22-36
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H319
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
UsesBikinin has been used: as a glycogen synthase kinase-3 (GSK3) inhibitor in Arabidopsis Col-0 seedlings to test its effect on gene expressionas a component of induction medium and as a GSK3 inhibitor to test its effect on mesophyll cells in Arabidopsis leaf discs or cotyledonsas a brassinosteroid agonist to test its effect on the leaf index of R. trichophyllus terrestrial leaves
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Compound notes
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