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

ID: ALA4571377

PubChem CID: 155562414

Max Phase: Preclinical

Molecular Formula: C13H15IN4O3

Molecular Weight: 402.19

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15IN4O3/c14-6-2-18(12-7(6)11(15)16-4-17-12)8-5-1-13(5,3-19)10(21)9(8)20/h2,4-5,8-10,19-21H,1,3H2,(H2,15,16,17)/t5-,8-,9+,10+,13+/m1/s1

Standard InChI Key:  IUCXONHNPHDHSF-WGDVLSMGSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   12.2468   -7.0229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9736   -6.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4413   -5.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2590   -5.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9440   -4.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1816   -4.1380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6852   -3.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1496   -2.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9533   -3.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9366   -3.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6367   -2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6175   -1.8029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3592   -3.0168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3726   -3.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726   -4.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1698   -5.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890   -6.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5263   -5.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8716   -6.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0577   -6.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8652   -4.4315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8798   -2.0406    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  2  0
  6  9  1  0
  9 10  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  9 15  1  0
  5 16  1  0
 16 17  1  0
  2 17  1  0
 17 18  1  0
 16 18  1  0
 17 19  1  1
 19 20  1  0
 16 21  1  1
  8 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571377

   ---

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: -0.11

#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: 13.24

CX Basic pKa: 5.51

CX LogP: -0.44

CX LogD: -0.45

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: 0.94

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