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

ID: ALA1093966

PubChem CID: 46884804

Max Phase: Preclinical

Molecular Formula: C20H35ClN10O5

Molecular Weight: 494.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)NCCCCCN(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/C20H34N10O5.ClH/c21-11(19(33)34)4-7-29(6-3-1-2-5-25-20(23)24)8-12-14(31)15(32)18(35-12)30-10-28-13-16(22)26-9-27-17(13)30;/h9-12,14-15,18,31-32H,1-8,21H2,(H,33,34)(H2,22,26,27)(H4,23,24,25);1H/t11-,12+,14+,15+,18+;/m0./s1

Standard InChI Key:  LJQFCIXUZOFNFG-CPQMNCBCSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   14.1250  -11.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.3114   -9.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6046  -10.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6169  -10.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9100  -11.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9224  -12.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2113  -12.6638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6416  -12.6423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2970   -8.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0130   -7.7460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8576   -7.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1884   -7.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5234   -7.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6435   -7.3480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7370   -7.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5989   -8.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7739   -8.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5211   -9.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8556   -9.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7287   -6.5604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8996   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9804   -7.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3124   -7.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3992   -8.6482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1496   -8.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8178   -8.4960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7317   -7.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3981   -7.1928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3067   -7.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5828   -7.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8765   -7.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1566   -7.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8900   -6.4715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4456   -7.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1385   -8.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9972   -8.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 23  1  0
  3  4  1  0
  6  7  1  0
 22 20  1  0
 20 21  2  0
 21 14  1  0
 16 11  1  0
 11 12  1  0
 22 23  2  0
 12 13  1  0
 23 24  1  0
 13 17  1  0
 24 25  2  0
  2  3  1  0
 25 26  1  0
 11 14  1  1
 26 27  2  0
 27 22  1  0
  6  8  2  0
 27 28  1  0
 15 10  1  0
 13 15  1  1
 10 29  1  0
 16 17  1  0
 29 30  1  0
  4  5  1  0
 30 31  1  0
  2  9  1  0
 31 32  1  0
 31 33  1  1
  5  6  1  0
 17 18  1  6
 32 34  1  0
 32 35  2  0
 16 19  1  6
 10 36  1  0
 36  9  1  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: 494.56

Molecular Weight (Monoisotopic): 494.2714

AlogP: -2.21

#Rotatable Bonds: 13

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: 2.81

CX Basic pKa: 11.90

CX LogP: -4.23

CX LogD: -6.26

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.08

Np Likeness Score: 0.60

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