(S)-2-Amino-4-((N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-5-chloropyrazine)-2-sulfonamido)butanoic acid

ID: ALA5284517

Max Phase: Preclinical

Molecular Formula: C18H22ClN9O7S

Molecular Weight: 543.95

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CC[C@H](N)C(=O)O)S(=O)(=O)c2cnc(Cl)cn2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H22ClN9O7S/c19-10-3-23-11(4-22-10)36(33,34)27(2-1-8(20)18(31)32)5-9-13(29)14(30)17(35-9)28-7-26-12-15(21)24-6-25-16(12)28/h3-4,6-9,13-14,17,29-30H,1-2,5,20H2,(H,31,32)(H2,21,24,25)/t8-,9+,13+,14+,17+/m0/s1

Standard InChI Key:  NUFHSMQFUWVWAB-ACSHICKMSA-N

Molfile:  

 
     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.5628    2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0968    1.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193    1.5211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531    0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3431    0.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961   -0.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -0.1154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320    1.0153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537    2.0284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638    0.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -0.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1374    0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    0.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998    1.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9019    2.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    1.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    2.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581    2.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    3.1145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4840    1.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1860    2.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.0741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519    0.9911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    0.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    1.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279   -0.6162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4019   -0.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    1.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384    0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445   -0.5958    0.0000 Cl  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  2  0
 32 33  1  0
 33 28  2  0
 27 34  2  0
 27 35  2  0
 31 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284517

   ---

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: 543.95

Molecular Weight (Monoisotopic): 543.1051

AlogP: -2.04

#Rotatable Bonds: 9

Polar Surface Area: 245.79

Molecular Species: ZWITTERION

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.00

CX Basic pKa: 9.09

CX LogP: -4.88

CX LogD: -4.88

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 0.13

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