3-Methoxybenzyl 2-(2-((S)-6-amino-3-((S)-2-amino-4-methylpentanamido)hexanoyl)-1-methylhydrazinyl)acetate

ID: ALA4163840

PubChem CID: 145959778

Max Phase: Preclinical

Molecular Formula: C23H39N5O5

Molecular Weight: 465.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(COC(=O)CN(C)NC(=O)C[C@H](CCCN)NC(=O)[C@@H](N)CC(C)C)c1

Standard InChI:  InChI=1S/C23H39N5O5/c1-16(2)11-20(25)23(31)26-18(8-6-10-24)13-21(29)27-28(3)14-22(30)33-15-17-7-5-9-19(12-17)32-4/h5,7,9,12,16,18,20H,6,8,10-11,13-15,24-25H2,1-4H3,(H,26,31)(H,27,29)/t18-,20-/m0/s1

Standard InChI Key:  MQPMNTMLCALFQY-ICSRJNTNSA-N

Molfile:  

     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
    5.0847  -22.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925  -21.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5002  -22.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2079  -21.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9156  -22.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2079  -21.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925  -21.0778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770  -21.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693  -22.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616  -21.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6233  -21.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3310  -22.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6233  -21.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0387  -21.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7464  -22.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0387  -21.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847  -20.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847  -19.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770  -21.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770  -19.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4541  -21.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1618  -22.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1602  -23.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8671  -23.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5757  -23.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5731  -22.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8657  -21.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770  -18.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693  -18.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847  -18.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925  -19.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2794  -21.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9885  -22.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  2  7  1  6
  1  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 11 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 20 28  1  0
 28 29  1  0
 28 30  1  0
 18 31  1  6
 26 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4163840

   ---

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: 465.60

Molecular Weight (Monoisotopic): 465.2951

AlogP: 0.69

#Rotatable Bonds: 15

Polar Surface Area: 149.01

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.18

CX Basic pKa: 9.90

CX LogP: -0.10

CX LogD: -3.56

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: 0.03

References

1. Taguchi A, Hamada K, Shiozuka M, Kobayashi M, Murakami S, Takayama K, Taniguchi A, Usui T, Matsuda R, Hayashi Y..  (2017)  Structure-Activity Relationship Study of Leucyl-3-epi-deoxynegamycin for Potent Premature Termination Codon Readthrough.,  8  (10): [PMID:29057051] [10.1021/acsmedchemlett.7b00269]

Source

Source(1):

• Scientific Literature