SID47201193

ID: ALA1365300

PubChem CID: 748515

Max Phase: Preclinical

Molecular Formula: C16H15NO5S

Molecular Weight: 333.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(NC(=O)Cc2cccs2)cc(C(=O)OC)c1

Standard InChI:  InChI=1S/C16H15NO5S/c1-21-15(19)10-6-11(16(20)22-2)8-12(7-10)17-14(18)9-13-4-3-5-23-13/h3-8H,9H2,1-2H3,(H,17,18)

Standard InChI Key:  LLFKSRAHIRSPNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -3.0300   -1.7974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9242    1.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6481    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6481   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7751   -2.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -2.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6387    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0
  1 20  1  0
  2 14  1  0
  2 22  1  0
  3 15  1  0
  3 23  1  0
  4 14  2  0
  5 15  2  0
  6 16  2  0
  7 10  1  0
  7 16  1  0
  8 11  2  0
  8 12  1  0
  8 14  1  0
  9 11  1  0
  9 13  2  0
  9 15  1  0
 10 12  2  0
 10 13  1  0
 16 18  1  0
 17 18  1  0
 17 19  2  0
 19 21  1  0
 20 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1365300

   Dimethyl 5-[(2-thiophen-2-ylacetyl)amino]benzene-1,3-dicarboxylate

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: 333.37

Molecular Weight (Monoisotopic): 333.0671

AlogP: 2.50

#Rotatable Bonds: 5

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: -1.72

References

1. PubChem BioAssay data set, 

2. Xiong H, Han J, Wang J, Lu W, Wang C, Chen Y, Fulin Lian, Zhang N, Liu YC, Zhang C, Ding H, Jiang H, Lu W, Luo C, Zhou B..  (2018)  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening.,  151  [PMID:29665527] [10.1016/j.ejmech.2018.02.005]

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(2):

• Scientific Literature
• PubChem BioAssays