N7-[(1'R,2'S,3'R,4'S)-2',3'-Dihydroxy-4'-aminocyclopentyl]-4-amino-5-iodopyrrolopyrimidine

ID: ALA4460859

PubChem CID: 155527924

Max Phase: Preclinical

Molecular Formula: C10H13IN6O2

Molecular Weight: 376.16

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(I)nn2[C@@H]1C[C@H](N)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H13IN6O2/c11-8-5-9(13)14-2-15-10(5)17(16-8)4-1-3(12)6(18)7(4)19/h2-4,6-7,18-19H,1,12H2,(H2,13,14,15)/t3-,4+,6+,7-/m0/s1

Standard InChI Key:  KGBDVGHICFMGKJ-HPQVQDLLSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   11.1263   -8.9509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1315   -9.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8453  -10.1767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8505  -10.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1462  -11.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4324  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4230  -10.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6429   -9.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3835   -9.1605    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    9.1663  -10.6036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6540  -11.2654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4041  -12.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8918  -12.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7131  -12.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4152  -13.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6746  -14.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6351  -13.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6298  -12.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765  -13.6101    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
  5  6  1  0
  6  7  2  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  6 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 12 18  1  0
 17 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4460859

   ---

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: 376.16

Molecular Weight (Monoisotopic): 376.0145

AlogP: -0.99

#Rotatable Bonds: 1

Polar Surface Area: 136.10

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.17

CX Basic pKa: 9.59

CX LogP: -1.46

CX LogD: -3.59

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.47

Np Likeness Score: 0.11

References

1. Toti KS, Osborne D, Ciancetta A, Boison D, Jacobson KA..  (2016)  South (S)- and North (N)-Methanocarba-7-Deazaadenosine Analogues as Inhibitors of Human Adenosine Kinase.,  59  (14): [PMID:27410258] [10.1021/acs.jmedchem.6b00689]

Source

Source(1):

• Scientific Literature