7-(Phenylethynyl)-4-aza-7,9-dideazaadenosine

ID: ALA4644331

PubChem CID: 156018096

Max Phase: Preclinical

Molecular Formula: C19H18N4O4

Molecular Weight: 366.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnn2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)cc(C#Cc3ccccc3)c12

Standard InChI:  InChI=1S/C19H18N4O4/c20-19-15-12(7-6-11-4-2-1-3-5-11)8-13(23(15)22-10-21-19)18-17(26)16(25)14(9-24)27-18/h1-5,8,10,14,16-18,24-26H,9H2,(H2,20,21,22)/t14-,16-,17-,18+/m1/s1

Standard InChI Key:  XCRZMSZGJGMUNI-DDBAPUKQSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.3751  -18.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1964  -18.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4508  -17.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7878  -17.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1250  -17.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8939  -19.1753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6801  -19.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3435  -17.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2325  -17.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7324  -18.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3138  -16.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4925  -16.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5652  -17.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8992  -17.9553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9834  -18.7698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7329  -19.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3991  -18.6195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3117  -17.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9760  -17.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7955  -16.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2798  -15.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7621  -14.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5718  -14.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0540  -14.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7239  -13.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9070  -13.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4284  -13.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  6
  2  7  1  6
  5  8  1  1
  3  9  1  1
  8 10  1  0
  9 14  1  0
 13 11  2  0
 11 12  1  0
 12  9  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 11 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644331

   ---

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: 366.38

Molecular Weight (Monoisotopic): 366.1328

AlogP: -0.13

#Rotatable Bonds: 2

Polar Surface Area: 126.13

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.70

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: 0.23

References

1. Li Q, Groaz E, Persoons L, Daelemans D, Herdewijn P..  (2020)  Synthesis and Antitumor Activity of C-7-Alkynylated and Arylated Pyrrolotriazine C-Ribonucleosides.,  11  (8): [PMID:32832030] [10.1021/acsmedchemlett.0c00269]

Source

Source(1):

• Scientific Literature