4-((1R,4R,6R)-4-Carboxy-4,6-dihydroxy-cyclohex-2-enyloxymethyl)-benzoic acid

ID: ALA153212

PubChem CID: 11472330

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@@H]2C=C[C@@](O)(C(=O)O)C[C@H]2O)cc1

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

Standard InChI Key:  SBLOMDGQPZRGOF-JMSVASOKSA-N

Molfile:  

     RDKit          2D

 22 23  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
   -2.0333   -0.9000    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
   -1.3208   -1.3125    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
   -2.7458   -1.3125    0.0000 O   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
   -0.6083   -0.8917    0.0000 C   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
   -2.0333   -0.0750    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
    0.1167   -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
   -0.6083   -2.5500    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  9  1  0
  6  3  2  0
  7  2  1  0
  8  6  1  0
  9 14  1  0
  8 10  1  6
 11  4  2  0
 12  5  2  0
 13 21  1  0
 14 22  2  0
  1 15  1  6
 16  4  1  0
 17  5  1  0
 18 10  1  0
 19 18  1  0
  7 20  1  1
 21 19  2  0
 22 19  1  0
  7  8  1  0
  9 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA153212

   4-((1R,4R,6R)-4-Carboxy-4,6-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: 3.26

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: -6.11

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.58

Np Likeness Score: 0.92

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