(1S,2S,3R,4R,5S)-1-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(aminomethyl)bicyclo[3.1.0]hexane-2,3-diol acetate

ID: ALA4539530

PubChem CID: 155549960

Max Phase: Preclinical

Molecular Formula: C13H16IN5O2

Molecular Weight: 401.21

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC[C@@H]1[C@@H](O)[C@@H](O)[C@@]2(n3cc(I)c4c(N)ncnc43)C[C@@H]12

Standard InChI:  InChI=1S/C13H16IN5O2/c14-7-3-19(12-8(7)11(16)17-4-18-12)13-1-6(13)5(2-15)9(20)10(13)21/h3-6,9-10,20-21H,1-2,15H2,(H2,16,17,18)/t5-,6-,9+,10+,13+/m0/s1

Standard InChI Key:  JPAKKFRFVDYXIO-KTCMLSIRSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    9.4260   -9.8089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4041  -10.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1044  -11.0644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0826  -11.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3564  -12.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6520  -11.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6779  -11.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8988  -10.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3950  -11.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8599  -12.0858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852  -12.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0524  -13.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8791  -13.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5497  -14.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792  -14.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7700  -13.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0876  -14.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7943  -13.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4370  -13.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0789  -12.6835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675   -9.9666    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.3502  -14.0349    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  2  0
  9 10  1  0
  6 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  1
 16 18  1  0
 11 18  1  0
 18 19  1  0
 11 19  1  0
 18 20  1  6
  8 21  1  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539530

   ---

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: 401.21

Molecular Weight (Monoisotopic): 401.0349

AlogP: -0.36

#Rotatable Bonds: 2

Polar Surface Area: 123.21

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.21

CX Basic pKa: 9.53

CX LogP: -0.68

CX LogD: -2.77

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 0.74

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