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

ID: ALA4525611

PubChem CID: 155543135

Max Phase: Preclinical

Molecular Formula: C13H14IN7O2

Molecular Weight: 427.21

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=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/C13H14IN7O2/c14-7-3-21(12-8(7)11(15)17-4-18-12)13-1-6(13)5(2-19-20-16)9(22)10(13)23/h3-6,9-10,22-23H,1-2H2,(H2,15,17,18)/t5-,6-,9+,10+,13+/m0/s1

Standard InChI Key:  KQMITLMWPOBFHU-KTCMLSIRSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.6087   -9.4098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868  -10.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872  -10.6652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2653  -11.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5391  -11.8861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347  -11.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607  -10.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817  -10.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780  -11.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428  -11.6866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680  -12.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2352  -13.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618  -13.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325  -13.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9621  -14.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530  -13.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706  -13.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771  -12.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6198  -13.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619  -12.2843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503   -9.5675    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332  -13.6357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416  -14.0975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537  -14.4982    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
 22 23  2  0
 23 24  2  0
M  CHG  2  23   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4525611

   ---

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: 427.21

Molecular Weight (Monoisotopic): 427.0254

AlogP: 1.00

#Rotatable Bonds: 3

Polar Surface Area: 145.95

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.21

CX Basic pKa: 5.47

CX LogP: 0.24

CX LogD: 0.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 0.73

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