2-(4-chlorophenyl)-N-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-2,2-difluoroacetamide

ID: ALA4742712

Cas Number: 1860875-51-9

PubChem CID: 118647211

Product Number: C419986, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H18ClF2N3O4

Molecular Weight: 461.85

Molecule Type: Unknown

In stock!

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C1CCC(N2Cc3cc(CNC(=O)C(F)(F)c4ccc(Cl)cc4)ccc3C2=O)C(=O)N1

Standard InChI:  InChI=1S/C22H18ClF2N3O4/c23-15-4-2-14(3-5-15)22(24,25)21(32)26-10-12-1-6-16-13(9-12)11-28(20(16)31)17-7-8-18(29)27-19(17)30/h1-6,9,17H,7-8,10-11H2,(H,26,32)(H,27,29,30)

Standard InChI Key:  PWBHUSLMHZLGRN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.0872  -19.0678    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999  -19.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083  -19.0653    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339  -18.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327  -19.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0408  -20.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390  -18.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7476  -18.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479  -19.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5308  -20.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0145  -19.3681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5304  -18.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318  -19.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2394  -20.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0531  -20.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4652  -19.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0576  -18.6650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2378  -18.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2824  -19.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8297  -17.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7827  -17.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247  -20.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173  -19.7789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093  -20.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939  -20.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0899  -19.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824  -20.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813  -21.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0937  -21.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -21.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086  -21.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738  -21.4102    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 13  1  0
 16 19  2  0
 18 20  2  0
 12 21  2  0
  5 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 24 31  2  0
 28 32  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4742712

    CC-90009

Associated Targets(Human)

CRBN Tclin Cereblon/GSPT1 (159 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRBN Tclin Cereblon/Ikaros (139 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRBN Tclin Cereblon/Aiolos (164 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A6 Tclin Solute carrier family 22 member 6 (265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A8 Tclin Solute carrier family 22 member 8 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A2 Tchem Solute carrier family 22 member 2 (261 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC47A2 Tchem Multidrug and toxin extrusion protein 2 (58 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MV4-11 (7307 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRBN Tclin Protein cereblon/DNA damage-binding protein 1 (47 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fibroblast (163371 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FGFR3 Tclin Fibroblast growth factor receptor 3 (7811 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRPF1 Tchem Peregrin (2217 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: YesParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 461.85Molecular Weight (Monoisotopic): 461.0954AlogP: 2.51#Rotatable Bonds: 5
Polar Surface Area: 95.58Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.09CX Basic pKa: CX LogP: 2.27CX LogD: 2.26
Aromatic Rings: 2Heavy Atoms: 32QED Weighted: 0.67Np Likeness Score: -0.51

References

1. Hansen JD,Correa M,Alexander M,Nagy M,Huang D,Sapienza J,Lu G,LeBrun LA,Cathers BE,Zhang W,Tang Y,Ammirante M,Narla RK,Piccotti JR,Pourdehnad M,Lopez-Girona A.  (2021)  CC-90009: A Cereblon E3 Ligase Modulating Drug That Promotes Selective Degradation of GSPT1 for the Treatment of Acute Myeloid Leukemia.,  64  (4.0): [PMID:33591756] [10.1021/acs.jmedchem.0c01489]
2. Nishiguchi G, Keramatnia F, Min J, Chang Y, Jonchere B, Das S, Actis M, Price J, Chepyala D, Young B, McGowan K, Slavish PJ, Mayasundari A, Jarusiewicz JA, Yang L, Li Y, Fu X, Garrett SH, Papizan JB, Kodali K, Peng J, Pruett Miller SM, Roussel MF, Mullighan C, Fischer M, Rankovic Z..  (2021)  Identification of Potent, Selective, and Orally Bioavailable Small-Molecule GSPT1/2 Degraders from a Focused Library of Cereblon Modulators.,  64  (11.0): [PMID:34042448] [10.1021/acs.jmedchem.0c01313]
3. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]
4. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]
5. Matyskiela, Mary E ME and 18 more authors.  2018-01-25  A Cereblon Modulator (CC-220) with Improved Degradation of Ikaros and Aiolos.  [PMID:28425720]