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

ID: ALA1088868

PubChem CID: 46884758

Max Phase: Preclinical

Molecular Formula: C18H31ClN10O5

Molecular Weight: 466.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)NCCCN(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/C18H30N10O5.ClH/c19-9(17(31)32)2-5-27(4-1-3-23-18(21)22)6-10-12(29)13(30)16(33-10)28-8-26-11-14(20)24-7-25-15(11)28;/h7-10,12-13,16,29-30H,1-6,19H2,(H,31,32)(H2,20,24,25)(H4,21,22,23);1H/t9-,10+,12+,13+,16+;/m0./s1

Standard InChI Key:  RTGQZUPEEAPPBO-SXOFXASESA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   14.3125   -3.5625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2775   -0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6071    0.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9409   -0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0630   -0.0203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1551   -0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0177   -1.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1924   -1.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9386   -1.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2756   -1.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1455    0.7668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3202    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3982   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7331   -0.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8176   -1.3223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5708   -1.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2361   -1.1670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -0.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8158    0.1338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4329   -0.4182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7246    0.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4192   -1.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0066   -0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2983    0.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5761   -0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3120    0.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8672    0.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5618   -1.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6970   -1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6833   -2.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9653   -2.8701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9474   -3.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2295   -4.0981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6558   -4.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  8  9  1  6
 18 19  1  0
  7 10  1  6
  6 20  1  0
  5 14  1  0
 20 21  1  0
  2  5  1  1
 20 22  1  0
  7  2  1  0
 21 23  1  0
 13 11  1  0
 23 24  1  0
 11 12  2  0
 24 25  1  0
 12  5  1  0
 24 26  1  1
  4  6  1  1
  7  8  1  0
 25 27  1  0
 25 28  2  0
 13 14  2  0
 22 29  1  0
  2  3  1  0
 29 30  1  0
 14 15  1  0
 30 31  1  0
  3  4  1  0
 31 32  1  0
 15 16  2  0
 32 33  1  0
  4  8  1  0
 32 34  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: 466.50

Molecular Weight (Monoisotopic): 466.2401

AlogP: -3.00

#Rotatable Bonds: 11

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: 1.99

CX Basic pKa: 11.77

CX LogP: -5.21

CX LogD: -6.93

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.09

Np Likeness Score: 0.58

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