(2S,5S)-2,5-diamino-6-((3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxydihydrofuran-2(3H)-ylidene)hexanoic acid

ID: ALA4550297

PubChem CID: 101982305

Max Phase: Preclinical

Molecular Formula: C15H21N7O5

Molecular Weight: 379.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O/C(=C\[C@@H](N)CC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H21N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h3-7,10-11,14,23-24H,1-2,16-17H2,(H,25,26)(H2,18,19,20)/b8-3-/t6-,7-,10+,11+,14+/m0/s1

Standard InChI Key:  YNKCTZQHSHSLNN-GHBFAAIGSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   17.5568   -4.1427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7960   -4.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1759   -4.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8365   -3.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5423   -5.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275   -3.8931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9007   -4.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2553   -5.4118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6825   -3.3271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7348   -5.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7889   -5.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4786   -4.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6378   -4.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0332   -5.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4690   -5.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7146   -4.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7324   -5.2424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2918   -3.8894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6947   -3.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3922   -2.8874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9772   -2.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2798   -3.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5622   -2.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8648   -3.3831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5420   -2.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2395   -1.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8245   -1.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  1  3  1  0
  1  4  1  0
  5  2  1  0
  2  6  1  0
  3  7  2  0
  3  8  1  0
  4  9  2  0
  5 10  1  0
  5 11  1  6
  6 12  1  0
  7 13  1  0
  8 14  2  0
 10 15  1  6
 12 16  2  0
 13 17  2  0
 13 18  1  0
 16 19  1  0
  7  9  1  0
 10 12  1  0
 14 17  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550297

   (2S,5S,6Z)-2,5-diamino-6-[(3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylidene]hexanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 379.38

Molecular Weight (Monoisotopic): 379.1604

AlogP: -1.94

#Rotatable Bonds: 6

Polar Surface Area: 208.65

Molecular Species: ZWITTERION

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.60

CX Basic pKa: 9.82

CX LogP: -5.37

CX LogD: -6.76

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 0.98

References

1. Zhu K, Song JL, Tao HR, Cheng ZQ, Jiang CS, Zhang H..  (2018)  Discovery of new potent protein arginine methyltransferase 5 (PRMT5) inhibitors by assembly of key pharmacophores from known inhibitors.,  28  (23-24): [PMID:30366617] [10.1016/j.bmcl.2018.10.026]

Source

Source(1):

• Scientific Literature