SID17432836

ID: ALA1348618

PubChem CID: 135425042

Max Phase: Preclinical

Molecular Formula: C16H11ClF3NO3

Molecular Weight: 357.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N/C=C(/C(=O)c2ccco2)C(=O)C(F)(F)F)cc1Cl

Standard InChI:  InChI=1S/C16H11ClF3NO3/c1-9-4-5-10(7-12(9)17)21-8-11(15(23)16(18,19)20)14(22)13-3-2-6-24-13/h2-8,21H,1H3/b11-8-

Standard InChI Key:  PAAFKDORHSTSLE-FLIBITNWSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.9488    4.0037    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3448   -0.9463    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6948   -0.9463    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -1.7713    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583   -1.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    0.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764    0.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198    1.5287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0909   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0909   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    3.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198    4.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5034   -2.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -2.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    3.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198    4.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0
  2 12  1  0
  3 12  1  0
  4 12  1  0
  5 13  1  0
  5 21  1  0
  6 10  2  0
  7 11  2  0
  8 14  1  0
  8 15  1  0
  9 10  1  0
  9 11  1  0
  9 14  2  0
 10 12  1  0
 11 13  1  0
 13 16  2  0
 15 17  1  0
 15 20  2  0
 16 22  1  0
 17 18  2  0
 18 19  1  0
 19 23  2  0
 19 24  1  0
 20 23  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1348618

   ---

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: 357.72

Molecular Weight (Monoisotopic): 357.0380

AlogP: 4.55

#Rotatable Bonds: 5

Polar Surface Area: 59.31

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.27

CX Basic pKa: ┄

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: -1.59

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. Zhou, Haibin H and 7 more authors.  2013-02-14  Structure-based design of high-affinity macrocyclic peptidomimetics to block the menin-mixed lineage leukemia 1 (MLL1) protein-protein interaction.  [PMID:23244744]

4. He, Shihan S and 10 more authors.  2014-02-27  High-affinity small-molecule inhibitors of the menin-mixed lineage leukemia (MLL) interaction closely mimic a natural protein-protein interaction.  [PMID:24472025]

5. Pollock, Jonathan and 6 more authors.  2015-09-24  Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes.  [PMID:26288158]

6. Borkin, Dmitry D and 12 more authors.  2016-02-11  Property Focused Structure-Based Optimization of Small Molecule Inhibitors of the Protein-Protein Interaction between Menin and Mixed Lineage Leukemia (MLL).  [PMID:26744767]

7. Borkin, Dmitry D and 12 more authors.  2018-06-14  Complexity of Blocking Bivalent Protein-Protein Interactions: Development of a Highly Potent Inhibitor of the Menin-Mixed-Lineage Leukemia Interaction.  [PMID:29738674]

8. Chen, Qi-Bin QB, Gao, Jie J, Zou, Guo-An GA, Xin, Xue-Lei XL and Aisa, Haji Akber HA.  2018-06-22  Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum.  [PMID:29775308]

9. Aguilar, Angelo A and 15 more authors.  2019-07-11  Structure-Based Discovery of M-89 as a Highly Potent Inhibitor of the Menin-Mixed Lineage Leukemia (Menin-MLL) Protein-Protein Interaction.  [PMID:31244110]

10. Xu, Shilin and 12 more authors.  2020-05-14  Discovery of M-808 as a Highly Potent, Covalent, Small-Molecule Inhibitor of the Menin-MLL Interaction with Strong In Vivo Antitumor Activity.  [PMID:32338903]

Source

Source(1):

• PubChem BioAssays