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

ID: ALA4518728

PubChem CID: 155541418

Max Phase: Preclinical

Molecular Formula: C13H15IN4O3

Molecular Weight: 402.19

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15IN4O3/c14-7-2-18(12-8(7)11(15)16-4-17-12)13-1-6(13)5(3-19)9(20)10(13)21/h2,4-6,9-10,19-21H,1,3H2,(H2,15,16,17)/t5-,6-,9+,10+,13+/m0/s1

Standard InChI Key:  MHLIMJFFKTUKND-KTCMLSIRSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    8.6294  -18.6349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6076  -19.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3072  -19.8893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2854  -20.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599  -21.1093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8560  -20.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8819  -19.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1035  -19.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692  -18.7849    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.6002  -20.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0647  -20.9099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902  -21.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2570  -22.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0830  -22.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7547  -23.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9841  -23.8144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9758  -22.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939  -23.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5513  -22.8536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000  -21.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6421  -22.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2852  -21.5070    0.0000 H   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  6
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  1
 18 19  1  0
 17 20  1  0
 12 20  1  0
 20 21  1  0
 12 21  1  0
 20 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4518728

   ---

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: 402.19

Molecular Weight (Monoisotopic): 402.0189

AlogP: -0.32

#Rotatable Bonds: 2

Polar Surface Area: 117.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 5.47

CX LogP: -0.58

CX LogD: -0.58

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 0.89

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