H2N-ART-NH2

ID: ALA1085864

PubChem CID: 24757930

Max Phase: Preclinical

Molecular Formula: C13H27N7O4

Molecular Weight: 345.40

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@H](N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](C(N)=O)[C@@H](C)O

Standard InChI:  InChI=1S/C13H27N7O4/c1-6(14)11(23)19-8(4-3-5-18-13(16)17)12(24)20-9(7(2)21)10(15)22/h6-9,21H,3-5,14H2,1-2H3,(H2,15,22)(H,19,23)(H,20,24)(H4,16,17,18)/t6-,7+,8-,9-/m0/s1

Standard InChI Key:  TXVGTYORMOSCJR-KZVJFYERSA-N

Molfile:  

     RDKit          2D

 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.7953  -14.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836  -15.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7953  -13.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836  -15.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279  -18.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545  -15.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428  -13.8628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428  -14.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545  -15.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428  -16.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428  -17.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269  -15.1003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889  -14.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2006  -15.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2006  -15.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889  -13.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269  -13.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102  -15.1007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279  -17.5747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438  -18.8122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889  -18.8128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693  -14.6884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1996  -13.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165  -14.6878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0
  8  7  2  0
  6  9  1  6
  9 10  1  0
 10 11  1  0
 13 12  1  1
 13 15  1  0
 15 14  2  0
 13 16  1  0
 16 17  1  0
  1 18  1  0
  8 12  1  0
  1  4  1  0
  4  2  2  0
  1  3  1  1
  5 21  2  0
 22  6  1  0
  4 22  1  0
  5 20  1  0
 16 23  1  1
 19  5  1  0
 11 19  1  0
 15 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085864

   H2N-Art-NH2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 345.40

Molecular Weight (Monoisotopic): 345.2125

AlogP: -3.57

#Rotatable Bonds: 10

Polar Surface Area: 209.44

Molecular Species: BASE

HBA: 6

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.04

CX Basic pKa: 11.70

CX LogP: -4.37

CX LogD: -7.15

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.11

Np Likeness Score: 0.28

References

1. Karatas H, Townsend EC, Bernard D, Dou Y, Wang S..  (2010)  Analysis of the binding of mixed lineage leukemia 1 (MLL1) and histone 3 peptides to WD repeat domain 5 (WDR5) for the design of inhibitors of the MLL1-WDR5 interaction.,  53  (14): [PMID:20575550] [10.1021/jm100139b]

2. Karatas, Hacer H, Townsend, Elizabeth C EC, Bernard, Denzil D, Dou, Yali Y and Wang, Shaomeng S.  2010-07-22  Analysis of the binding of mixed lineage leukemia 1 (MLL1) and histone 3 peptides to WD repeat domain 5 (WDR5) for the design of inhibitors of the MLL1-WDR5 interaction.  [PMID:20575550]

3. Bolshan, Yuri Y and 16 more authors.  2013-03-14  Synthesis, Optimization, and Evaluation of Novel Small Molecules as Antagonists of WDR5-MLL Interaction.  [PMID:24900672]

4. Getlik, Matthäus M and 17 more authors.  2016-03-24  Structure-Based Optimization of a Small Molecule Antagonist of the Interaction Between WD Repeat-Containing Protein 5 (WDR5) and Mixed-Lineage Leukemia 1 (MLL1).  [PMID:26958703]

5. Li, Dong-Dong DD and 9 more authors.  2016-08-08  Structure-based design and synthesis of small molecular inhibitors disturbing the interaction of MLL1-WDR5.  [PMID:27116709]

6. Li, Dong-Dong DD and 8 more authors.  2016-11-29  High-affinity small molecular blockers of mixed lineage leukemia 1 (MLL1)-WDR5 interaction inhibit MLL1 complex H3K4 methyltransferase activity.  [PMID:27598236]

7. Li, Dong-Dong DD and 5 more authors.  2016-11-15  Structure-based design of ester compounds to inhibit MLL complex catalytic activity by targeting mixed lineage leukemia 1 (MLL1)-WDR5 interaction.  [PMID:27720555]

8. Wang, Feng F and 17 more authors.  2018-07-12  Discovery of Potent 2-Aryl-6,7-dihydro-5 H-pyrrolo[1,2- a]imidazoles as WDR5-WIN-Site Inhibitors Using Fragment-Based Methods and Structure-Based Design.  [PMID:29889518]

9. Ye, Xiaoqing X and 11 more authors.  2019-02-15  The identification of novel small-molecule inhibitors targeting WDR5-MLL1 interaction through fluorescence polarization based high-throughput screening.  [PMID:30626558]

10. Tian, Jianhua and 24 more authors.  2020-01-23  Discovery and Structure-Based Optimization of Potent and Selective WD Repeat Domain 5 (WDR5) Inhibitors Containing a Dihydroisoquinolinone Bicyclic Core.  [PMID:31858797]

11. Chacón Simon, Selena and 14 more authors.  2020-04-23  Discovery of WD Repeat-Containing Protein 5 (WDR5)-MYC Inhibitors Using Fragment-Based Methods and Structure-Based Design.  [PMID:32223236]

Source

Source(1):

• Scientific Literature