(S)-4-(((1-(2-(amino(iminio)methylamino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)amino)-2-ammoniobutanoate chloride

ID: ALA1091914

PubChem CID: 46884807

Max Phase: Preclinical

Molecular Formula: C20H32ClN13O5

Molecular Weight: 533.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)NCCn1cc(CN(CC[C@H](N)C(=O)O)C[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C20H31N13O5.ClH/c21-11(19(36)37)1-3-31(5-10-6-32(30-29-10)4-2-25-20(23)24)7-12-14(34)15(35)18(38-12)33-9-28-13-16(22)26-8-27-17(13)33;/h6,8-9,11-12,14-15,18,34-35H,1-5,7,21H2,(H,36,37)(H2,22,26,27)(H4,23,24,25);1H/t11-,12+,14+,15+,18+;/m0./s1

Standard InChI Key:  IBIYXEJKJLSHPI-CPQMNCBCSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   16.7813  -15.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.5455  -17.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5574  -16.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3984  -16.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7291  -15.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0641  -16.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1834  -16.1079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2787  -16.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1416  -17.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3166  -17.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0617  -17.9305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3965  -17.9305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2667  -15.3213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4418  -15.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5206  -16.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8524  -16.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9373  -17.4075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6899  -17.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3583  -17.2558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2700  -16.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9365  -15.9531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8499  -16.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1287  -16.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4212  -16.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6999  -16.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4350  -15.2344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9918  -16.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6855  -17.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8252  -17.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0761  -17.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5156  -17.9945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9175  -18.7152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7268  -18.5552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6906  -17.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2817  -18.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4567  -18.7192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0478  -19.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4638  -20.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2228  -19.4398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0
 20 15  1  0
  6 10  1  0
 20 21  1  0
  8  3  1  0
 10 11  1  6
  3 22  1  0
  9 12  1  6
 22 23  1  0
  7 16  1  0
 23 24  1  0
  2  3  1  0
 24 25  1  0
  4  7  1  1
 24 26  1  1
 15 13  1  0
 13 14  2  0
 25 27  1  0
 25 28  2  0
 14  7  1  0
  2 29  1  0
 29 30  2  0
  6  8  1  1
 15 16  2  0
  9 10  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
 16 17  1  0
 31 34  1  0
  9  4  1  0
 34 35  1  0
 17 18  2  0
 35 36  1  0
  4  5  1  0
 36 37  1  0
 18 19  1  0
 37 38  1  0
  5  6  1  0
 37 39  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: 533.55

Molecular Weight (Monoisotopic): 533.2571

AlogP: -3.59

#Rotatable Bonds: 12

Polar Surface Area: 278.48

Molecular Species: ZWITTERION

HBA: 15

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.47

CX Basic pKa: 11.75

CX LogP: -5.42

CX LogD: -7.13

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.08

Np Likeness Score: -0.12

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