Methyl 4-(2,3-dinitroxypropyl)benzoate

ID: ALA2205644

PubChem CID: 71455878

Max Phase: Preclinical

Molecular Formula: C11H12N2O8

Molecular Weight: 300.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methyl 4-(2,3-Dinitroxypropyl)Benzoate | CHEMBL2205644|Methyl 4-(2,3-Dinitroxypropyl)Benzoate

Canonical SMILES:  COC(=O)c1ccc(CC(CO[N+](=O)[O-])O[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C11H12N2O8/c1-19-11(14)9-4-2-8(3-5-9)6-10(21-13(17)18)7-20-12(15)16/h2-5,10H,6-7H2,1H3

Standard InChI Key:  XSIICEOWVNFMCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   14.1325  -48.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8470  -48.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8470  -49.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5615  -50.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2760  -49.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2760  -48.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5615  -48.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1325  -47.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4181  -48.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9904  -50.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7049  -49.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7049  -48.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4194  -48.4963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4194  -47.6713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1338  -47.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7049  -47.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4194  -50.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1338  -49.7338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1338  -48.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8483  -50.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7036  -48.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  1  0
 14 15  2  0
 14 16  1  0
 13 14  1  0
 12 13  1  0
 18 19  2  0
 18 20  1  0
 17 18  1  0
 11 17  1  0
  5 10  1  0
  9 21  1  0
M  CHG  4  14   1  16  -1  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2205644

   Methyl 4-(2,3-Dinitroxypropyl)Benzoate

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: 300.22

Molecular Weight (Monoisotopic): 300.0594

AlogP: 0.80

#Rotatable Bonds: 8

Polar Surface Area: 131.04

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.39

Np Likeness Score: -0.04

References

1. Chegaev K, Riganti C, Lazzarato L, Rolando B, Guglielmo S, Campia I, Fruttero R, Bosia A, Gasco A..  (2011)  Nitric oxide donor doxorubicins accumulate into Doxorubicin-resistant human colon cancer cells inducing cytotoxicity.,  2  (7): [PMID:24900337] [10.1021/ml100302t]

Source

Source(1):

• Scientific Literature