(S)-2-amino-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(prop-2-ynyl)amino)butanoic acid

ID: ALA1091913

PubChem CID: 46884806

Max Phase: Preclinical

Molecular Formula: C17H23N7O5

Molecular Weight: 405.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H23N7O5/c1-2-4-23(5-3-9(18)17(27)28)6-10-12(25)13(26)16(29-10)24-8-22-11-14(19)20-7-21-15(11)24/h1,7-10,12-13,16,25-26H,3-6,18H2,(H,27,28)(H2,19,20,21)/t9-,10+,12+,13+,16+/m0/s1

Standard InChI Key:  UUGVUWJWRVIDOL-UOYPZJKHSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -0.3545  -17.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426  -16.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984  -16.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291  -15.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641  -16.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834  -15.9787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3787  -15.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416  -17.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166  -17.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617  -17.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965  -17.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667  -15.1922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5418  -15.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6206  -15.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524  -16.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373  -17.2784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899  -17.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4583  -17.1266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3700  -16.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0365  -15.8239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501  -15.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713  -16.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788  -15.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001  -16.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650  -15.1052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082  -15.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145  -17.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748  -17.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917  -18.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  1
 14 15  2  0
  8  9  1  0
 15 16  1  0
  8  3  1  0
 16 17  2  0
  3  4  1  0
 17 18  1  0
  4  5  1  0
 18 19  2  0
 19 14  1  0
  5  9  1  0
 19 20  1  0
  7  2  1  0
  9 10  1  6
  2 21  1  0
  8 11  1  6
 21 22  1  0
  6 15  1  0
 22 23  1  0
  1  2  1  0
 23 24  1  0
  3  6  1  1
 23 25  1  1
 14 12  1  0
 12 13  2  0
 24 26  1  0
 24 27  2  0
 13  6  1  0
  1 28  1  0
 28 29  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091913

   (2S)-2-amino-4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-prop-2-ynylamino]butanoic acid

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: 405.42

Molecular Weight (Monoisotopic): 405.1761

AlogP: -2.24

#Rotatable Bonds: 8

Polar Surface Area: 185.87

Molecular Species: ZWITTERION

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.82

CX Basic pKa: 9.19

CX LogP: -4.50

CX LogD: -4.51

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: 0.46

References

1. Dowden J, Hong W, Parry RV, Pike RA, Ward SG..  (2010)  Toward the development of potent and selective bisubstrate inhibitors of protein arginine methyltransferases.,  20  (7): [PMID:20219369] [10.1016/j.bmcl.2010.02.069]

2. Schwickert M, Fischer TR, Zimmermann RA, Hoba SN, Meidner JL, Weber M, Weber M, Stark MM, Koch J, Jung N, Kersten C, Windbergs M, Lyko F, Helm M, Schirmeister T..  (2022)  Discovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment.,  65  (14.0): [PMID:35849534] [10.1021/acs.jmedchem.2c00388]

Source

Source(1):

• Scientific Literature