(1S(R),2S(R),5R(S),6R(S))-5-Bromo-9-oxabicyclo[4.2.1]nonan-2-yl nitrate

ID: ALA1096674

PubChem CID: 46888469

Max Phase: Preclinical

Molecular Formula: C8H12BrNO4

Molecular Weight: 266.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])O[C@@H]1CC[C@H](Br)[C@@H]2CC[C@H]1O2

Standard InChI:  InChI=1S/C8H12BrNO4/c9-5-1-2-8(14-10(11)12)7-4-3-6(5)13-7/h5-8H,1-4H2/t5-,6-,7+,8+/m0/s1

Standard InChI Key:  KLUZIRRRZFQGPA-RULNZFCNSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    9.7049   -5.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7050   -4.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2836   -4.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2837   -6.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1108   -6.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6943   -5.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6942   -4.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1108   -4.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4547   -5.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4612   -6.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1793   -7.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7513   -7.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9432   -5.9849    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.7270   -5.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4419   -4.4952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9529   -4.5042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  3  1  0
  6  9  1  6
  1  2  1  0
  9 10  1  0
  2  3  1  0
  1  4  1  0
 10 11  2  0
 10 12  1  0
  4  5  1  0
  1 13  1  6
  5  6  1  0
  2 14  1  0
  7 14  1  0
  6  7  1  0
  7 15  1  1
  7  8  1  0
  2 16  1  1
M  CHG  2  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1096674

   [(1R,2R,5S,6S)-5-bromo-9-oxabicyclo[4.2.1]nonan-2-yl] nitrate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 266.09

Molecular Weight (Monoisotopic): 264.9950

AlogP: 1.67

#Rotatable Bonds: 2

Polar Surface Area: 61.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.03

CX LogD: 2.03

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.43

Np Likeness Score: 0.57

References

1. Sentürk M, Talaz O, Ekinci D, Cavdar H, Küfrevioğlu OI..  (2009)  In vitro inhibition of human erythrocyte glutathione reductase by some new organic nitrates.,  19  (13): [PMID:19447620] [10.1016/j.bmcl.2009.04.087]

2. Ekinci D, Cavdar H, Talaz O, Sentürk M, Supuran CT..  (2010)  NO-releasing esters show carbonic anhydrase inhibitory action against human isoforms I and II.,  18  (10): [PMID:20430631] [10.1016/j.bmc.2010.03.082]

Source

Source(1):

• Scientific Literature