(1R(S),2R(S),3S(R),4S(R))-2,3-Dihydroxycyclo-hexane-1,4-diyl dinitrate

ID: ALA556671

PubChem CID: 45273032

Max Phase: Preclinical

Molecular Formula: C6H10N2O8

Molecular Weight: 238.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])OC1CCC(O[N+](=O)[O-])C(O)C1O

Standard InChI:  InChI=1S/C6H10N2O8/c9-5-3(15-7(11)12)1-2-4(6(5)10)16-8(13)14/h3-6,9-10H,1-2H2

Standard InChI Key:  UUWYEFLMUYTPBD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    1.5357   -2.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -4.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -4.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -4.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   -2.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -2.8773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -2.8773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -4.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -3.2898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -4.1148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -2.8773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -4.1148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -4.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -3.2898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  1  6  1  0
  6  9  1  0
  2  3  1  0
  3 10  1  0
  3  4  1  0
  9 11  1  0
  4  5  1  0
 10 12  1  0
  5  6  1  0
 11 13  2  0
 11 14  1  0
  1  7  1  0
  1  2  1  0
 12 15  2  0
 12 16  1  0
M  CHG  4  11   1  12   1  14  -1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA556671

   (2,3-Dihydroxy-4-nitrooxycyclohexyl) 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: 238.15

Molecular Weight (Monoisotopic): 238.0437

AlogP: -1.34

#Rotatable Bonds: 4

Polar Surface Area: 145.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.67

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: -0.55

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.45

Np Likeness Score: 0.54

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]

Source

Source(1):

• Scientific Literature