(1R,4R,5R)-1,5-Dihydroxy-4-(4-nitro-benzyloxy)-cyclohex-2-enecarboxylic acid

ID: ALA152151

PubChem CID: 11415622

Max Phase: Preclinical

Molecular Formula: C14H15NO7

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C[C@@H](OCc2ccc([N+](=O)[O-])cc2)[C@H](O)C1

Standard InChI:  InChI=1S/C14H15NO7/c16-11-7-14(19,13(17)18)6-5-12(11)22-8-9-1-3-10(4-2-9)15(20)21/h1-6,11-12,16,19H,7-8H2,(H,17,18)/t11-,12-,14+/m1/s1

Standard InChI Key:  WNMVBDKWHSREPB-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   -2.0333   -0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375   -0.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -1.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -2.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    1.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  8  1  0
  4  6  2  0
  2  5  1  1
  6 11  1  0
  7  1  1  0
  8 11  1  0
  9  1  1  0
 10  1  2  0
 11 12  1  6
 12 18  1  0
 13  5  2  0
 14  7  1  0
 15  7  2  0
  2 16  1  6
 17  5  1  0
 18 19  1  0
 19 21  2  0
  8 20  1  1
 21 15  1  0
 22 14  2  0
 22 19  1  0
  4  2  1  0
M  CHG  2   1   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA152151

   (1R,4R,5R)-1,5-Dihydroxy-4-(4-nitro-benzyloxy)-cyclohex-2-enecarboxylic acid

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: 309.27

Molecular Weight (Monoisotopic): 309.0849

AlogP: 0.62

#Rotatable Bonds: 5

Polar Surface Area: 130.13

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 0.71

CX LogD: -2.74

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: 0.45

References

1. González-Bello C, Lence E, Toscano MD, Castedo L, Coggins JR, Abell C..  (2003)  Parallel solid-phase synthesis and evaluation of inhibitors of Streptomyces coelicolor type II dehydroquinase.,  46  (26): [PMID:14667226] [10.1021/jm030987q]

Source

Source(1):

• Scientific Literature