(2S,3S,4R,5R)-5-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydrofuran-2-carboxylic acid

ID: ALA5169980

PubChem CID: 168270288

Max Phase: Preclinical

Molecular Formula: C11H11IN4O5

Molecular Weight: 406.14

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(I)cn2[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H11IN4O5/c12-3-1-16(9-4(3)8(13)14-2-15-9)10-6(18)5(17)7(21-10)11(19)20/h1-2,5-7,10,17-18H,(H,19,20)(H2,13,14,15)/t5-,6+,7-,10+/m0/s1

Standard InChI Key:  YQMPDCWPJYMOPN-HEZDBXPZSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.1740   -1.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906   -0.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7199    0.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344    0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1488    0.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344    1.4796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    0.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913    0.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -0.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584   -1.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    0.2640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7357    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    1.5250    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200    0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -1.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344   -1.1171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344   -0.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488    0.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  3  4  1  6
  4  5  1  0
  4  6  2  0
  7  3  1  0
  7  8  1  0
  8  9  1  0
  9  2  1  0
  9 10  1  1
  8 11  1  6
 11 12  1  0
 13 12  2  0
 13 14  1  0
 15 13  1  0
 16 15  1  0
 16 11  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 15 20  2  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5169980

   ---

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: 406.14

Molecular Weight (Monoisotopic): 405.9774

AlogP: -0.68

#Rotatable Bonds: 2

Polar Surface Area: 143.72

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.69

CX Basic pKa: 6.77

CX LogP: -2.23

CX LogD: -2.87

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: 0.77

References

1. Lee S, Kim J, Jo J, Chang JW, Sim J, Yun H..  (2021)  Recent advances in development of hetero-bivalent kinase inhibitors.,  216  [PMID:33730624] [10.1016/j.ejmech.2021.113318]

Source

Source(1):

• Scientific Literature