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

ID: ALA346315

PubChem CID: 11818376

Max Phase: Preclinical

Molecular Formula: C14H15FO5

Molecular Weight: 282.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(OCc2ccccc2F)C=C[C@@H](O)[C@H](O)C1

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

Standard InChI Key:  ZBBIFWSHYNLOBP-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    0.9500    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    1.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292    0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -0.5375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.5250    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
  1  7  1  6
  8 10  1  0
  9  5  1  0
 10  7  1  0
 11  4  2  0
 12  8  2  0
 13  4  1  0
 14 12  1  0
  6 15  1  1
  9 16  1  6
 17  8  1  0
 18 12  1  0
 19 17  2  0
 20 19  1  0
  9  6  1  0
 20 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA346315

   (1R,4R,5R)-1-(2-Fluoro-benzyloxy)-4,5-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: 3.53

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: -2.45

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: 0.54

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