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

ID: ALA4468490

PubChem CID: 44755075

Max Phase: Preclinical

Molecular Formula: C11H12N4NaO6P

Molecular Weight: 328.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ccn2[C@@H]1O[C@@H]2COP(=O)([O-])O[C@H]2[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C11H13N4O6P.Na/c12-9-5-1-2-15(10(5)14-4-13-9)11-7(16)8-6(20-11)3-19-22(17,18)21-8;/h1-2,4,6-8,11,16H,3H2,(H,17,18)(H2,12,13,14);/q;+1/p-1/t6-,7-,8-,11-;/m1./s1

Standard InChI Key:  CPVKEMPANUKIKS-DQSPBIHISA-M

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   22.0687   -5.5688    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   21.3790   -5.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5937   -4.4285    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.8037   -4.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7563   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -3.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3477   -2.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9391   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6904   -3.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8966   -3.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3459   -3.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3941   -4.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7878   -2.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2359   -4.6610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9356   -2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1233   -2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1017   -3.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3910   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3857   -4.3343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0905   -4.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8020   -4.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8038   -3.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5128   -3.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6832   -2.4020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.3395   -4.7050    0.0000 H   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
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: 328.22

Molecular Weight (Monoisotopic): 328.0573

AlogP: -0.21

#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: 7.51

CX LogP: -3.66

CX LogD: -3.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.61

Np Likeness Score: 1.07

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