8-bromo-7-deazaadenosine-3',5'-cyclic monophosphate sodium

ID: ALA4549036

PubChem CID: 155548968

Max Phase: Preclinical

Molecular Formula: C11H11BrN4NaO6P

Molecular Weight: 407.12

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1cc(Br)n2[C@@H]1O[C@@H]2COP(=O)([O-])O[C@H]2[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C11H12BrN4O6P.Na/c12-6-1-4-9(13)14-3-15-10(4)16(6)11-7(17)8-5(21-11)2-20-23(18,19)22-8;/h1,3,5,7-8,11,17H,2H2,(H,18,19)(H2,13,14,15);/q;+1/p-1/t5-,7-,8-,11-;/m1./s1

Standard InChI Key:  VQQUWDVOCJKUMP-YCSZXMBFSA-M

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   38.1857   -5.0973    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   37.4917   -4.8536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7064   -4.0653    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   36.9164   -4.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8690   -3.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1234   -2.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4604   -2.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0518   -3.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8031   -2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0093   -2.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4586   -3.2879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5068   -4.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9005   -2.6079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3486   -4.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.0483   -1.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2360   -1.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2144   -2.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5037   -3.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4984   -3.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2032   -4.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9147   -3.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9165   -3.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6255   -2.7558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7959   -2.0389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   39.4522   -4.3418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   40.8306   -1.1538    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  2  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11  3  1  0
  3 12  1  0
  6 13  1  1
  5 14  1  6
 13 18  1  0
 17 15  1  0
 15 16  2  0
 16 13  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
  9 24  1  6
  8 25  1  1
 16 26  1  0
M  CHG  2   1   1   2  -1
M  END

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: 407.12

Molecular Weight (Monoisotopic): 405.9678

AlogP: 0.55

#Rotatable Bonds: 1

Polar Surface Area: 141.95

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.83

CX Basic pKa: 6.43

CX LogP: -3.16

CX LogD: -2.45

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: 0.86

References

1. Lelle M, Otte M, Thon S, Bertinetti D, Herberg FW, Benndorf K..  (2019)  Chemical synthesis and biological activity of novel brominated 7-deazaadenosine-3',5'-cyclic monophosphate derivatives.,  27  (8): [PMID:30879860] [10.1016/j.bmc.2019.03.024]

Source

Source(1):

• Scientific Literature