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

ID: ALA4472686

PubChem CID: 155536078

Max Phase: Preclinical

Molecular Formula: C19H19IN4O3

Molecular Weight: 478.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@@H]1[C@@H](O)[C@@H](O)[C@@]2(n3cc(I)c4c(Nc5ccccc5)ncnc43)C[C@@H]12

Standard InChI:  InChI=1S/C19H19IN4O3/c20-13-7-24(19-6-12(19)11(8-25)15(26)16(19)27)18-14(13)17(21-9-22-18)23-10-4-2-1-3-5-10/h1-5,7,9,11-12,15-16,25-27H,6,8H2,(H,21,22,23)/t11-,12-,15+,16+,19+/m0/s1

Standard InChI Key:  AMOJSRYPEDUPSR-DBFNJNRKSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   12.8374  -18.4052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156  -19.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5168  -19.6622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4950  -20.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7678  -20.8846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0626  -20.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0886  -19.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3086  -19.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0738  -18.5555    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   10.8042  -20.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697  -20.6849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9945  -21.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4623  -22.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2900  -22.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9590  -22.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1889  -23.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1784  -22.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952  -22.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7510  -22.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2027  -21.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8462  -22.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4865  -21.2832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5571  -18.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2513  -18.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9703  -18.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9925  -17.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894  -16.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5732  -17.1996    0.0000 C   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
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4472686

   ---

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: 478.29

Molecular Weight (Monoisotopic): 478.0502

AlogP: 1.84

#Rotatable Bonds: 4

Polar Surface Area: 103.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 4.25

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 0.20

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