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

ID: ALA4440555

PubChem CID: 155514707

Max Phase: Preclinical

Molecular Formula: C33H44N4O7

Molecular Weight: 608.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CC12CC3CC(CC(C3)C1)C2)NCCCOCCOCCCNc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O

Standard InChI:  InChI=1S/C33H44N4O7/c38-27-7-6-26(30(40)36-27)37-31(41)24-4-1-5-25(29(24)32(37)42)34-8-2-10-43-12-13-44-11-3-9-35-28(39)20-33-17-21-14-22(18-33)16-23(15-21)19-33/h1,4-5,21-23,26,34H,2-3,6-20H2,(H,35,39)(H,36,38,40)

Standard InChI Key:  OCEADRRXDVSTSC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   34.2379   -6.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.2111   -3.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7583   -3.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9650   -3.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5031   -3.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6352   -2.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   29.6171   -2.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  8 12  2  0
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 16 20  2  0
 21 22  1  0
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 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4440555

   ---

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: 608.74

Molecular Weight (Monoisotopic): 608.3210

AlogP: 3.04

#Rotatable Bonds: 15

Polar Surface Area: 143.14

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.59

CX Basic pKa: 2.07

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.20

Np Likeness Score: -0.58

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