4-((1R,4R,5R)-1-Carboxy-4,5-dihydroxy-cyclohex-2-enyloxymethyl)-benzoic acid

ID: ALA152738

PubChem CID: 11255268

Max Phase: Preclinical

Molecular Formula: C15H16O7

Molecular Weight: 308.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CO[C@@]2(C(=O)O)C=C[C@@H](O)[C@H](O)C2)cc1

Standard InChI:  InChI=1S/C15H16O7/c16-11-5-6-15(14(20)21,7-12(11)17)22-8-9-1-3-10(4-2-9)13(18)19/h1-6,11-12,16-17H,7-8H2,(H,18,19)(H,20,21)/t11-,12-,15+/m1/s1

Standard InChI Key:  GFNIEDZYXVWBOK-JMSVASOKSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    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
    1.0875   -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
   -2.5000    0.0958    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
    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   -0.3125    0.0000 C   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
    2.1542   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2125   -0.3167    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
   -1.0708    0.1000    0.0000 C   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
   -2.5000    0.9208    0.0000 O   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
   -0.3500   -1.1417    0.0000 C   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
   -1.0708   -1.5542    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
    1.7917   -4.0375    0.0000 O   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  9  1  0
  6  3  2  0
  7  2  1  0
  1  8  1  6
  9 14  1  0
 10  6  1  0
 11  4  2  0
 12  5  2  0
 13 20  1  0
 14 21  2  0
 15  4  1  0
 16  5  1  0
 17  8  1  0
 18 17  1  0
  7 19  1  1
 20 18  2  0
 21 18  1  0
 10 22  1  6
  7 10  1  0
  9 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA152738

   4-((1R,4R,5R)-1-Carboxy-4,5-dihydroxy-cyclohex-2-enyloxymethyl)-benzoic 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: 308.29

Molecular Weight (Monoisotopic): 308.0896

AlogP: 0.41

#Rotatable Bonds: 5

Polar Surface Area: 124.29

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.14

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: -6.14

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.58

Np Likeness Score: 1.10

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