(2S)-2-amino-4-(N-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-4-chloro-3-nitrobenzenesulfonamido)butanoic acid

ID: ALA5286276

Max Phase: Preclinical

Molecular Formula: C20H23ClN8O9S

Molecular Weight: 586.97

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CC[C@H](N)C(=O)O)S(=O)(=O)c2ccc(Cl)c([N+](=O)[O-])c2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H23ClN8O9S/c21-10-2-1-9(5-12(10)29(34)35)39(36,37)27(4-3-11(22)20(32)33)6-13-15(30)16(31)19(38-13)28-8-26-14-17(23)24-7-25-18(14)28/h1-2,5,7-8,11,13,15-16,19,30-31H,3-4,6,22H2,(H,32,33)(H2,23,24,25)/t11-,13+,15+,16+,19+/m0/s1

Standard InChI Key:  LAEPWYDZBRWDHX-KFAHYOAQSA-N

Molfile:  

 
     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
    0.8401    2.0551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3740    1.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967    1.4887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306    0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206    0.0423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0367   -0.1482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468    0.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9098    0.9828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937    1.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313    1.9960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6297    2.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4894    0.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6250    2.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9098    2.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3751    0.9585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5295    0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -0.6076    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -0.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753   -1.4737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -1.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -0.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780    1.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1615    0.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10  8  1  0
  4 10  2  0
 11 10  1  0
 12 11  2  0
 12  3  1  0
  2 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  6
 17 15  1  0
  1 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  2  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 33 37  1  0
 37 28  2  0
 27 38  2  0
 27 39  2  0
M  CHG  2  34   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5286276

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 586.97

Molecular Weight (Monoisotopic): 586.0997

AlogP: -0.92

#Rotatable Bonds: 10

Polar Surface Area: 263.15

Molecular Species: ZWITTERION

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.95

CX Basic pKa: 9.09

CX LogP: -3.32

CX LogD: -3.32

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: -0.41

References

1. Schwickert M, Zimmermann RA, Habeck T, Hoba SN, Nidoieva Z, Fischer TR, Stark MM, Kersten C, Lermyte F, Helm M, Schirmeister T..  (2023)  Covalent S-Adenosylhomocysteine-Based DNA Methyltransferase 2 Inhibitors with a New Type of Aryl Warhead.,  14  (6): [PMID:37312859] [10.1021/acsmedchemlett.3c00062]

Source

Source(1):

• Scientific Literature