2-Adamantan-1-yl-N-{2-[2-(2-{2-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-acetamide

ID: ALA4516967

PubChem CID: 155540419

Max Phase: Preclinical

Molecular Formula: C33H44N4O8

Molecular Weight: 624.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CC12CC3CC(CC(C3)C1)C2)NCCOCCOCCOCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O

Standard InChI:  InChI=1S/C33H44N4O8/c38-27-5-4-26(30(40)36-27)37-31(41)24-2-1-3-25(29(24)32(37)42)34-6-8-43-10-12-45-13-11-44-9-7-35-28(39)20-33-17-21-14-22(18-33)16-23(15-21)19-33/h1-3,21-23,26,34H,4-20H2,(H,35,39)(H,36,38,40)

Standard InChI Key:  HIGNLENJNGHQRT-UHFFFAOYSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4516967

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 624.74

Molecular Weight (Monoisotopic): 624.3159

AlogP: 2.27

#Rotatable Bonds: 16

Polar Surface Area: 152.37

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.59

CX Basic pKa: 1.29

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.19

Np Likeness Score: -0.64

References

1. Steinebach C, Sosič I, Lindner S, Bricelj A, Kohl F, Ng YLD, Monschke M, Wagner KG, Krönke J, Gütschow M..  (2019)  A MedChem toolbox for cereblon-directed PROTACs.,  10  (6): [PMID:31304001] [10.1039/C9MD00185A]

2. 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(1):

• Scientific Literature