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

ID: ALA345567

PubChem CID: 9972592

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](OCc2ccccc2[N+](=O)[O-])[C@H](O)C1

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

Standard InChI Key:  KKNDQIGUXIEMRA-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   -0.7375   -3.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    1.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417    0.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  9  1  0
  4  1  1  0
  5  7  2  0
  2  6  1  1
  7 12  1  0
  8  4  2  0
  9 12  1  0
 10  1  1  0
 11  1  2  0
 12 13  1  6
 13 14  1  0
 14  8  1  0
 15  6  2  0
  2 16  1  6
 17  6  1  0
  9 18  1  1
 19  4  1  0
 20  8  1  0
 21 19  2  0
 22 21  1  0
 20 22  2  0
  5  2  1  0
M  CHG  2   1   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA345567

   (1R,4R,5R)-1,5-Dihydroxy-4-(2-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: 2.92

CX Basic pKa: ┄

CX LogP: 0.71

CX LogD: -2.77

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: 0.30

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