(1R,4R,5R)-3-(3-(4-fluorophenoxy)prop-1-enyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid

ID: ALA1823558

PubChem CID: 17756720

Max Phase: Preclinical

Molecular Formula: C16H17FO6

Molecular Weight: 324.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(/C=C/COc2ccc(F)cc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C16H17FO6/c17-11-3-5-12(6-4-11)23-7-1-2-10-8-16(22,15(20)21)9-13(18)14(10)19/h1-6,8,13-14,18-19,22H,7,9H2,(H,20,21)/b2-1+/t13-,14-,16+/m1/s1

Standard InChI Key:  XOSLAWHUCVDCJK-IOFCFPLSSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   13.8292   -6.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2458   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6582   -6.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5375   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5375   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2495   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9615   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9615   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4831   -6.4658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2435   -5.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6754   -8.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2495   -9.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8236   -8.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1086   -8.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3947   -8.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6796   -8.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9657   -8.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2516   -8.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5382   -8.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5389   -9.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2590  -10.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9695   -9.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8256  -10.0870    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  6
  4  2  1  0
  5 13  1  0
  5  6  1  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
  8  2  1  0
 16 17  1  0
  2  1  1  0
 17 18  2  0
  3  9  1  0
 18 19  1  0
  2  3  1  1
 19 20  2  0
  3 10  2  0
 20 21  1  0
  4  5  2  0
 21 22  2  0
 22 17  1  0
  7 11  1  1
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1823558

   (1R,4R,5R)-3-[(E)-3-(4-fluorophenoxy)prop-1-enyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic 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: 324.30

Molecular Weight (Monoisotopic): 324.1009

AlogP: 0.63

#Rotatable Bonds: 5

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.32

CX Basic pKa: ┄

CX LogP: 0.37

CX LogD: -3.05

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 0.72

References

1. Tizón L, Otero JM, Prazeres VF, Llamas-Saiz AL, Fox GC, van Raaij MJ, Lamb H, Hawkins AR, Ainsa JA, Castedo L, González-Bello C..  (2011)  A prodrug approach for improving antituberculosis activity of potent Mycobacterium tuberculosis type II dehydroquinase inhibitors.,  54  (17): [PMID:21780742] [10.1021/jm2006063]

Source

Source(1):

• Scientific Literature