sodium (4aR,6R,7R,7aS)-6-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

ID: ALA4442766

PubChem CID: 155516248

Max Phase: Preclinical

Molecular Formula: C11H11BrN4NaO6P

Molecular Weight: 407.12

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(Br)cn2[C@@H]1O[C@@H]2COP(=O)([O-])O[C@H]2[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C11H12BrN4O6P.Na/c12-4-1-16(10-6(4)9(13)14-3-15-10)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:  YPFPUPBCJADEDM-YCSZXMBFSA-M

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   39.6884  -15.2330    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   39.0972  -14.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3119  -14.1688    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   38.5219  -14.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4745  -13.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7289  -12.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0659  -12.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6573  -13.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4086  -12.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6148  -12.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0641  -13.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1123  -14.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.5060  -12.7114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9540  -14.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6538  -12.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8415  -11.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8199  -12.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1092  -13.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1039  -14.0746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.8087  -14.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5202  -14.0795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.5220  -13.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2310  -12.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.4014  -12.1423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.0577  -14.4453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   44.2034  -11.4512    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
 15 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: 0.85

CX Basic pKa: 6.75

CX LogP: -2.88

CX LogD: -2.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: 0.96

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