(2S)-2-amino-4-[[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-5-yl]methylamino]butanoic acid

ID: ALA5207209

PubChem CID: 168297433

Max Phase: Preclinical

Molecular Formula: C14H23N5O6

Molecular Weight: 357.37

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1CNCC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C14H23N5O6/c15-8(13(22)23)1-2-17-4-7-5-19(14(24)18-12(7)16)11-3-9(21)10(6-20)25-11/h5,8-11,17,20-21H,1-4,6,15H2,(H,22,23)(H2,16,18,24)/t8-,9-,10+,11+/m0/s1

Standard InChI Key:  RSZJXFKNJBHJCQ-UKKRHICBSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.5863    1.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    1.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    1.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    0.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5863    0.4401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867   -0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1931   -0.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6053   -0.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536    0.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300   -0.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8424   -0.9638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054   -1.6777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2710    0.4401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    1.6775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005    1.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4138    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4138   -0.7969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    1.2649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    0.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 10 12  1  1
 12 13  1  0
  9 14  1  6
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  3 19  1  0
  1 20  2  0
 18 21  1  0
 21 22  1  0
 21 23  1  1
 22 24  2  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207209

   ---

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: 357.37

Molecular Weight (Monoisotopic): 357.1648

AlogP: -2.64

#Rotatable Bonds: 8

Polar Surface Area: 185.95

Molecular Species: ZWITTERION

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.77

CX Basic pKa: 9.19

CX LogP: -5.82

CX LogD: -5.85

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.27

Np Likeness Score: 0.96

References

1. Lamiable-Oulaidi F, Harijan RK, Shaffer KJ, Crump DR, Sun Y, Du Q, Gulab SA, Khan AA, Luxenburger A, Woolhouse AD, Sidoli S, Tyler PC, Schramm VL..  (2022)  Synthesis and Characterization of Transition-State Analogue Inhibitors against Human DNA Methyltransferase 1.,  65  (7.0): [PMID:35324190] [10.1021/acs.jmedchem.1c01869]

Source

Source(1):

• Scientific Literature