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

ID: ALA156711

PubChem CID: 11209049

Max Phase: Preclinical

Molecular Formula: C14H15NO7

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(OCc2ccccc2[N+](=O)[O-])C=C[C@@H](O)[C@H](O)C1

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

Standard InChI Key:  HNHYMFKEBUOPPZ-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   -1.0708   -2.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -2.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -2.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -3.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -4.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  6
  3  2  1  0
  4  1  1  0
  5  2  1  0
  2  6  1  1
  7  5  2  0
  8  4  2  0
  9  3  1  0
 10 14  1  0
 11  1  1  0
 12  1  2  0
 13  7  1  0
 14  8  1  0
 15  6  2  0
 16  6  1  0
  9 17  1  1
 13 18  1  6
 19  4  1  0
 20  8  1  0
 21 19  2  0
 22 21  1  0
 20 22  2  0
 13  9  1  0
M  CHG  2   1   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA156711

   (1R,4R,5R)-4,5-Dihydroxy-1-(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: 3.04

CX Basic pKa: ┄

CX LogP: 0.71

CX LogD: -2.76

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: 0.49

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