SID49717079

ID: ALA1387422

Cas Number: 894554-89-3

PubChem CID: 20919929

Max Phase: Preclinical

Molecular Formula: C27H31N5O2

Molecular Weight: 457.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-n2nc3c(=O)n(CCCC(=O)NCC(C)c4ccccc4)nc(C)c3c2C)cc1

Standard InChI:  InChI=1S/C27H31N5O2/c1-18-12-14-23(15-13-18)32-21(4)25-20(3)29-31(27(34)26(25)30-32)16-8-11-24(33)28-17-19(2)22-9-6-5-7-10-22/h5-7,9-10,12-15,19H,8,11,16-17H2,1-4H3,(H,28,33)

Standard InChI Key:  HZNKNJCWLQLQMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.1151    1.6259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -0.4366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0991   -0.0241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6142    0.6434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4006    0.3884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4006   -0.4366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.8009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -0.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6142   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151    0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -0.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9241   -0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691   -1.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3366   -0.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3366    0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -1.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1616   -0.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1616    0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5741   -0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3991   -0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -0.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7441    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -0.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    1.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7441   -0.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0
  2 25  2  0
  3  4  1  0
  3 10  1  0
  3 13  1  0
  4  9  2  0
  5  6  1  0
  5 11  1  0
  5 15  1  0
  6 12  2  0
  7 25  1  0
  7 28  1  0
  8  9  1  0
  8 10  2  0
  8 12  1  0
  9 11  1  0
 10 14  1  0
 12 18  1  0
 13 16  2  0
 13 17  1  0
 15 22  1  0
 16 19  1  0
 17 20  2  0
 19 21  2  0
 20 21  1  0
 21 24  1  0
 22 23  1  0
 23 25  1  0
 26 27  1  0
 26 29  2  0
 26 30  1  0
 27 28  1  0
 27 33  1  0
 29 31  1  0
 30 32  2  0
 31 34  2  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1387422

   Deltazinone

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 457.58

Molecular Weight (Monoisotopic): 457.2478

AlogP: 4.21

#Rotatable Bonds: 8

Polar Surface Area: 81.81

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -1.70

References

1. PubChem BioAssay data set, 

2. Jiang Y, Zhuang C, Chen L, Lu J, Dong G, Miao Z, Zhang W, Li J, Sheng C..  (2017)  Structural Biology-Inspired Discovery of Novel KRAS-PDEδ Inhibitors.,  60  (22): [PMID:28929751] [10.1021/acs.jmedchem.7b01243]

3. Chen L, Zhuang C, Lu J, Jiang Y, Sheng C..  (2018)  Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design.,  61  (6): [PMID:29510040] [10.1021/acs.jmedchem.8b00057]

4. Cheng J, Li Y, Wang X, Dong G, Sheng C..  (2020)  Discovery of Novel PDEδ Degraders for the Treatment of KRAS Mutant Colorectal Cancer.,  63  (14): [PMID:32603594] [10.1021/acs.jmedchem.0c00929]

5. Guo M, He S, Cheng J, Li Y, Dong G, Sheng C..  (2022)  Hydrophobic Tagging-Induced Degradation of PDEδ in Colon Cancer Cells.,  13  (2.0): [PMID:35178186] [10.1021/acsmedchemlett.1c00670]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays