(1R,4R,5R)-4-(3-Fluoro-benzyloxy)-1,5-dihydroxy-cyclohex-2-enecarboxylic acid

ID: ALA153675

PubChem CID: 11448918

Max Phase: Preclinical

Molecular Formula: C14H15FO5

Molecular Weight: 282.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C[C@@H](OCc2cccc(F)c2)[C@H](O)C1

Standard InChI:  InChI=1S/C14H15FO5/c15-10-3-1-2-9(6-10)8-20-12-4-5-14(19,13(17)18)7-11(12)16/h1-6,11-12,16,19H,7-8H2,(H,17,18)/t11-,12-,14+/m1/s1

Standard InChI Key:  OLLTZNQLDFMQDE-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    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
    2.2125   -1.2750    0.0000 C   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
    0.7792    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
   -0.6083   -2.5500    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
    2.9250   -1.6875    0.0000 O   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
   -2.0333   -2.5417    0.0000 F   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   -1.3125    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  1  1  0
  3  1  1  0
  1  4  1  1
  5  3  2  0
  6  2  1  0
  7  5  1  0
  7  8  1  6
  9  4  2  0
  1 10  1  6
 11  4  1  0
 12  8  1  0
 13 16  2  0
 14 13  1  0
  6 15  1  1
 16 12  1  0
 17 14  1  0
 18 20  2  0
 19 18  1  0
 20 16  1  0
  7  6  1  0
 19 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA153675

   (1R,4R,5R)-4-(3-Fluoro-benzyloxy)-1,5-dihydroxy-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: 282.27

Molecular Weight (Monoisotopic): 282.0904

AlogP: 0.85

#Rotatable Bonds: 4

Polar Surface Area: 86.99

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.34

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: -2.50

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: 0.41

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