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

ID: ALA4458520

PubChem CID: 155526367

Max Phase: Preclinical

Molecular Formula: C12H14IN5O2

Molecular Weight: 387.18

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(I)cn2[C@]12C[C@H]1[C@H](N)[C@@H](O)[C@H]2O

Standard InChI:  InChI=1S/C12H14IN5O2/c13-5-2-18(11-6(5)10(15)16-3-17-11)12-1-4(12)7(14)8(19)9(12)20/h2-4,7-9,19-20H,1,14H2,(H2,15,16,17)/t4-,7-,8+,9+,12+/m0/s1

Standard InChI Key:  HOMYCFIXZDWAGO-NVJYAXLPSA-N

Molfile:  

 
     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   13.4895  -10.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4676  -11.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1680  -11.4468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1462  -12.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4199  -12.6680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7154  -12.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7414  -11.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9623  -11.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4585  -11.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9235  -12.4683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6486  -13.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1157  -13.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9425  -13.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6131  -14.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8427  -15.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8334  -14.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1510  -14.7710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8576  -13.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004  -13.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1423  -13.0661    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7309  -10.3490    0.0000 I   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
M  END

Alternative Forms

1. Parent:

   

   ALA4458520

   ---

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: 387.18

Molecular Weight (Monoisotopic): 387.0192

AlogP: -0.60

#Rotatable Bonds: 1

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: 13.10

CX Basic pKa: 9.64

CX LogP: -0.69

CX LogD: -2.87

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: 0.67

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