(S)-2-amino-4-((((2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(propyl)amino)butanoic acid

ID: ALA5187924

PubChem CID: 168278266

Max Phase: Preclinical

Molecular Formula: C17H27N7O5

Molecular Weight: 409.45

Names and Identifiers

Canonical SMILES:  CCCN(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/C17H27N7O5/c1-2-4-23(5-3-9(18)17(27)28)6-10-12(25)13(26)16(29-10)24-8-22-11-14(19)20-7-21-15(11)24/h7-10,12-13,16,25-26H,2-6,18H2,1H3,(H,27,28)(H2,19,20,21)/t9-,10-,12-,13-,16-/m0/s1

Standard InChI Key:  DRPLAOXTIXKDEC-UQMYLEDRSA-N

Molfile:  

 
     RDKit          2D

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   -2.4443   -0.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960   -0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -0.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -1.2770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5383   -1.4724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3505   -0.0388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    0.4401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121    0.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620   -0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049   -0.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765   -0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9868   -1.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4577   -1.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2428   -2.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8384   -0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    0.0641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -0.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884   -0.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3505   -0.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -1.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522    0.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522    2.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083    0.3095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  6  5  1  0
  2  7  1  0
  7  6  2  0
  4  8  1  0
  3  9  1  0
  1 10  1  0
 10  9  2  0
 11  1  1  1
 12 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 15 16  1  6
 14 17  1  6
 13 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 19 26  1  0
 26 27  1  0
 27 28  1  0
 22 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5187924

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.45

Molecular Weight (Monoisotopic): 409.2074

AlogP: -1.46

#Rotatable Bonds: 9

Polar Surface Area: 185.87

Molecular Species: ZWITTERION

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.81

CX Basic pKa: 9.19

CX LogP: -3.97

CX LogD: -4.06

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 0.52

References

1. Talukdar A, Mukherjee A, Bhattacharya D..  (2022)  Fascinating Transformation of SAM-Competitive Protein Methyltransferase Inhibitors from Nucleoside Analogues to Non-Nucleoside Analogues.,  65  (3.0): [PMID:35014841] [10.1021/acs.jmedchem.1c01208]

Source

Source(1):

• Scientific Literature