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

ID: ALA157011

PubChem CID: 11300717

Max Phase: Preclinical

Molecular Formula: C15H15NO5

Molecular Weight: 289.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CO[C@@H]2C=C[C@@](O)(C(=O)O)C[C@H]2O)cc1

Standard InChI:  InChI=1S/C15H15NO5/c16-8-10-1-3-11(4-2-10)9-21-13-5-6-15(20,14(18)19)7-12(13)17/h1-6,12-13,17,20H,7,9H2,(H,18,19)/t12-,13-,15+/m1/s1

Standard InChI Key:  OSLSQUDNWVROBG-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 21 22  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
   -2.7583   -0.4875    0.0000 N   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
   -2.0333   -0.9000    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
   -1.3208   -1.3125    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
    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
   -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
    0.1125   -1.3042    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
  2  1  1  0
  3  1  1  0
  1  4  1  1
  5  8  3  0
  6  3  2  0
  7  2  1  0
  8 12  1  0
  9  6  1  0
  9 10  1  6
 11  4  2  0
 12 18  2  0
  1 13  1  6
 14  4  1  0
 15 10  1  0
 16 15  1  0
  7 17  1  1
 18 21  1  0
 19 20  2  0
 20 16  1  0
 21 16  2  0
  9  7  1  0
 19 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA157011

   (1R,4R,5R)-4-(4-Cyano-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: 289.29

Molecular Weight (Monoisotopic): 289.0950

AlogP: 0.58

#Rotatable Bonds: 4

Polar Surface Area: 110.78

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.39

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: -2.78

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: 0.50

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