(S)-4-((4-(amino(iminio)methylamino)butyl)(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)amino)-2-ammoniobutanoate chloride

ID: ALA1090536

PubChem CID: 46884802

Max Phase: Preclinical

Molecular Formula: C19H33ClN10O5

Molecular Weight: 480.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)NCCCCN(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/C19H32N10O5.ClH/c20-10(18(32)33)3-6-28(5-2-1-4-24-19(22)23)7-11-13(30)14(31)17(34-11)29-9-27-12-15(21)25-8-26-16(12)29;/h8-11,13-14,17,30-31H,1-7,20H2,(H,32,33)(H2,21,25,26)(H4,22,23,24);1H/t10-,11+,13+,14+,17+;/m0./s1

Standard InChI Key:  QNPNXAZPMZIUBA-DQDNRUGSSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    2.5000  -11.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -8.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -9.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -9.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0053  -10.7996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797  -11.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231  -10.7602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570  -12.0170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -8.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718   -7.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4693   -7.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -6.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349   -7.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -7.0829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3495   -7.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -8.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -8.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325   -8.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4673   -8.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376   -6.2963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126   -6.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914   -7.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -7.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -8.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7607   -8.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291   -8.2308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3408   -7.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0073   -6.9281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -7.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005   -7.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -7.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941   -6.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9373   -7.0133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437   -8.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  6
 16 19  1  6
 14 23  1  0
  5  6  1  0
  3  4  1  0
 22 20  1  0
 20 21  2  0
 21 14  1  0
  6  7  1  0
 16 11  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
 12 13  1  0
 24 25  2  0
 13 17  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 27 22  1  0
 11 14  1  1
 27 28  1  0
 15 10  1  0
  6  8  2  0
 10 29  1  0
 13 15  1  1
 29 30  1  0
 16 17  1  0
 30 31  1  0
  4  5  1  0
 31 32  1  0
  2  9  1  0
 31 33  1  1
  9 10  1  0
 32 34  1  0
 32 35  2  0
M  END

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: 480.53

Molecular Weight (Monoisotopic): 480.2557

AlogP: -2.61

#Rotatable Bonds: 12

Polar Surface Area: 247.77

Molecular Species: ZWITTERION

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.82

CX Basic pKa: 11.82

CX LogP: -4.68

CX LogD: -6.56

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.09

Np Likeness Score: 0.59

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]

Source

Source(1):

• Scientific Literature