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

ID: ALA4519937

PubChem CID: 155541950

Max Phase: Preclinical

Molecular Formula: C13H13ClIN3O3

Molecular Weight: 421.62

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H13ClIN3O3/c14-11-8-7(15)2-18(12(8)17-4-16-11)13-1-6(13)5(3-19)9(20)10(13)21/h2,4-6,9-10,19-21H,1,3H2/t5-,6-,9+,10+,13+/m0/s1

Standard InChI Key:  JSPYYYZOBAOTLX-KTCMLSIRSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    3.4753  -18.2489    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4535  -19.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531  -19.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313  -20.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057  -20.7230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021  -20.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280  -19.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496  -19.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7153  -18.3988    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464  -19.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108  -20.5236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363  -21.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030  -21.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289  -22.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6009  -22.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8301  -23.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220  -22.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402  -22.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023  -22.4671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8460  -21.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883  -21.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315  -21.1207    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:

   

   ALA4519937

   ---

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: 421.62

Molecular Weight (Monoisotopic): 420.9690

AlogP: 0.75

#Rotatable Bonds: 2

Polar Surface Area: 91.40

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 1.75

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 0.64

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