3-(5-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione
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Basic information
- CAS
191732-70-4- Standard SMILES
Nc1ccc2c(c1)CN(C1CCC(=O)NC1=O)C2=O- InChIKey
WLUIQUZGNPAKRL-UHFFFAOYSA-N- Molecular formula
- C13H13N3O3
- Average molar mass
- 259.26 g/mol
- Monoisotopic mass
- 259.09569128
Names & identifiers
- Preferred name
- 3-(5-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione
- IUPAC
- 3-(6-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
- English name
- 3-(5-Amino-1-oxo-isoindolin-2-yl)piperidine-2,6-dione
- Molecular formula
- C13H13N3O3
- Molecular weight
- 259.26
Names & synonyms
191732-70-43-(5-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dioneRefChem:493636844-702-2C5 Lenalidomide3-(5-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione3-(5-Amino-1-oxo-isoindolin-2-yl)piperidine-2,6-dioneMFCD31692701CHEMBL402062-(2,6-Dioxo-3-piperidinyl)-5-aminoisoindoline-1-one3-(6-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione3-(5-Amino-1-oxo-2-isoindolinyl)piperidine-2,6-dione
Show more names
2-(2,6-Dioxopiperidin-3-yl)phthalimidine 5-NH2Trifarotene Impurity 5C5 Lenalidomide, 10 mM in DMSOC-5 Lenalidomide,C5 Lenalidomide1,4']Bipiperidinyl-4-carboxylic acid ethyl ester3-(5-amino-l-oxoisoindolin- 2-yl)piperidine-2,6-dione
Lenalidomide-5'-NH2starbld0010763Lenalidomide Impurity 112(3S)-3-(5-amino-1-oxo-isoindolin-2-yl)piperidine-2,6-dioneSCHEMBL501751orb1218548orb1298226SCHEMBL29044392
Database identifiers
- CAS
191732-70-4- PubChem CID
- 9816615
- DTXSID
DTXSID101380298- ChEMBL
CHEMBL40206- EC Number
- 844-702-2
- Nikkaji
- J1.121.691I
Properties
Computed structural propertiesFilling in
- XLogP
- -0.5
- Topological polar surface area
- 92.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 437
Physicochemical properties
- Boiling point
- 634.5 · 634.5±55.0 °C(Predicted)
- Density
- 1.46 · 1.460±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 10.83 · 10.83±0.40(Predicted)
- form
- Solid
- color
- Off-white to gray
- InChI
- InChI=1S/C13H13N3O3/c14-8-1-2-9-7(5-8)6-16(13(9)19)10-3-4-11(17)15-12(10)18/h1-2,5,10H,3-4,6,14H2,(H,15,17,18)
- InChIKey
- WLUIQUZGNPAKRL-UHFFFAOYSA-N
- SMILES
- N1C(=O)CCC(N2CC3=C(C2=O)C=CC(N)=C3)C1=O
- UNSPSC Code
- 12352101 · 12352101
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 361 d-H373 · H361d-H373
- Precautionary statements
- 201 · P201-P308+P313
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 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 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 (50%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- target organs
- Blood
- Hazard statements
- H361d-H373
- Hazard Classifications
- Repr. 2STOT RE 2
- Precautionary statements
- P201-P308+P313
Chemistry & industry
Applications
Description3-(5-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione is a lenalidomide analog that can be useful in PROTAC research.
UsesC5 Lenalidomide (Lenalidomide 5'-amine) is a thalidomide analog and is a potent inhibitor of TNF-alpha production (IC50=100 μM in LPS stimulated human PBMC)[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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