IBERDOMIDE

ID: ALA3989927

Cas Number: 1323403-33-3

PubChem CID: 67335295

Product Number: I414161, Order Now?

Max Phase: Phase

Molecular Formula: C25H27N3O5

Molecular Weight: 449.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Iberdomide | CC-220 | Iberdomide|1323403-33-3|cc-220|(S)-3-(4-((4-(Morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione|Iberdomide [USAN]|CC220|8V66F27X44|(3s)-3-[4-({4-[(Morpholin-4-Yl)methyl]phenyl}methoxy)-1-Oxo-1,3-Dihydro-2h-Isoindol-2-Yl]piperidine-2,6-Dione|(3S)-3-[4-({4-[(morpholin-4-yl)methyl]phenyl}methoxy)-1-oxo-2,3-dihydro-1H-isoindol-2-yl]piperidine-2,6-dione|(3S)-3-[7-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione|2,6-PiperidShow More⌵

Synonyms from Alternative Forms(3): Cc-220 hydrochloride | Iberdomide hydrochloride | CC-220

Canonical SMILES:  O=C1CC[C@H](N2Cc3c(OCc4ccc(CN5CCOCC5)cc4)cccc3C2=O)C(=O)N1

Standard InChI:  InChI=1S/C25H27N3O5/c29-23-9-8-21(24(30)26-23)28-15-20-19(25(28)31)2-1-3-22(20)33-16-18-6-4-17(5-7-18)14-27-10-12-32-13-11-27/h1-7,21H,8-16H2,(H,26,29,30)/t21-/m0/s1

Standard InChI Key:  IXZOHGPZAQLIBH-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -4.7440    0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4543    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4460   -0.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275   -0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171   -0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254    0.2714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4802    0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4802   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -0.5099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4802    1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488    0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488    1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    1.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    0.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183    1.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994    1.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4747    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    1.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360    0.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2607    0.3700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6924    1.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380    0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    2.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043   -0.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171    1.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 14 15  1  0
 15 16  1  0
 13 16  2  0
 11 14  1  0
 17 18  2  0
 19 20  2  0
 17 20  1  0
 18 13  1  0
 16 19  1  0
 22 23  1  0
 21 23  1  0
 19 22  1  0
 21 20  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 24 29  1  0
  6 30  1  0
 30  8  1  0
 21 31  2  0
 26 23  1  1
 27 32  2  0
 29 33  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA3989927

   IBERDOMIDE HYDROCHLORIDE

2. Parent:

   

   ALA3989927

   Iberdomide (CC220)

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 449.51

Molecular Weight (Monoisotopic): 449.1951

AlogP: 1.86

#Rotatable Bonds: 6

Polar Surface Area: 88.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: 6.91

CX LogP: 1.41

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.68

Np Likeness Score: -0.54

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Matyskiela ME, Zhang W, Man HW, Muller G, Khambatta G, Baculi F, Hickman M, LeBrun L, Pagarigan B, Carmel G, Lu CC, Lu G, Riley M, Satoh Y, Schafer P, Daniel TO, Carmichael J, Cathers BE, Chamberlain PP..  (2018)  A Cereblon Modulator (CC-220) with Improved Degradation of Ikaros and Aiolos.,  61  (2): [PMID:28425720] [10.1021/acs.jmedchem.6b01921]

3. Xiao D, Wang YJ, Hu XB, Kan WJ, Zhang Q, Jiang X, Zhou YB, Li J, Lu W..  (2019)  Design, synthesis and biological evaluation of the thioether-containing lenalidomide analogs with anti-proliferative activities.,  176  [PMID:31125896] [10.1016/j.ejmech.2019.05.035]

4. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

5. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

6. Unpublished dataset, 

7. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

8. Maiwald S,Heim C,Hernandez Alvarez B,Hartmann MD.  (2021)  Sweet and Blind Spots in E3 Ligase Ligand Space Revealed by a Thermophoresis-Based Assay.,  12  (1): [PMID:33488967] [10.1021/acsmedchemlett.0c00440]

9. Kong NR, Liu H, Che J, Jones LH..  (2021)  Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.,  12  (11.0): [PMID:34795877] [10.1021/acsmedchemlett.1c00475]

10. Zhang Z, Liu X, Zhao L, Zhou Y, Shi J, Chen W, Li J..  (2022)  A review on the treatment of multiple myeloma with small molecular agents in the past five years.,  229  [PMID:34974338] [10.1016/j.ejmech.2021.114053]

11. 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]

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data