(2S)-N-[(1S)-1-[4-carbamoyl-2-(4-fluorophenyl)-1H-imidazol-5-yl]-7-oxo-nonyl]-6-ethyl-6-azaspiro[2.5]octane-2-carboxamide

ID: ALA4785376

PubChem CID: 162665723

Max Phase: Preclinical

Molecular Formula: C29H40FN5O3

Molecular Weight: 525.67

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)CCCCC[C@H](NC(=O)[C@H]1CC12CCN(CC)CC2)c1[nH]c(-c2ccc(F)cc2)nc1C(N)=O

Standard InChI:  InChI=1S/C29H40FN5O3/c1-3-21(36)8-6-5-7-9-23(32-28(38)22-18-29(22)14-16-35(4-2)17-15-29)24-25(26(31)37)34-27(33-24)19-10-12-20(30)13-11-19/h10-13,22-23H,3-9,14-18H2,1-2H3,(H2,31,37)(H,32,38)(H,33,34)/t22-,23+/m1/s1

Standard InChI Key:  QEADHPNYEASZRQ-PKTZIBPZSA-N

Molfile:  

 
     RDKit          2D

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   36.0431  -26.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4537  -25.5131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0492  -24.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2300  -24.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.3006  -23.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8493  -23.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.0016  -24.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   31.2805  -21.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   34.4434  -22.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2606  -22.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7384  -21.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5556  -21.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0375  -21.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8949  -22.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.8188  -24.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1540  -25.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3008  -23.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7054  -25.2975    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 19 32  1  0
 33 32  1  6
 32 34  2  0
  8 35  1  0
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  1 36  1  0
 33  1  1  0
  4 37  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785376

   ---

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: 525.67

Molecular Weight (Monoisotopic): 525.3115

AlogP: 4.52

#Rotatable Bonds: 13

Polar Surface Area: 121.18

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.35

CX Basic pKa: 9.00

CX LogP: 3.01

CX LogD: 1.79

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: -0.43

References

1. Clausen DJ,Liu J,Yu W,Duffy JL,Chung CC,Myers RW,Klein DJ,Fells J,Holloway K,Wu J,Wu G,Howell BJ,Barnard RJO,Kozlowski J.  (2020)  Development of a selective HDAC inhibitor aimed at reactivating the HIV latent reservoir.,  30  (17.0): [PMID:32738976] [10.1016/j.bmcl.2020.127367]

2. Yu W, Fells J, Clausen D, Liu J, Klein DJ, Christine Chung C, Myers RW, Wu J, Wu G, Howell BJ, Barnard RJO, Kozlowski J..  (2021)  Discovery of macrocyclic HDACs 1, 2, and 3 selective inhibitors for HIV latency reactivation.,  47  [PMID:34091041] [10.1016/j.bmcl.2021.128168]

Source

Source(1):

• Scientific Literature