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

ID: ALA351107

PubChem CID: 11231562

Max Phase: Preclinical

Molecular Formula: C15H15NO5

Molecular Weight: 289.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CO[C@@]2(C(=O)O)C=C[C@@H](O)[C@H](O)C2)cc1

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

Standard InChI Key:  WXNVQPLMGBVJEG-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 21 22  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
   -3.2208    0.5125    0.0000 N   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
   -2.5000    0.0958    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
    1.7917   -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
   -1.7833   -0.3125    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
    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
    1.7917   -4.0375    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
   -0.3583   -0.3125    0.0000 C   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
  2  1  1  0
  3  1  1  0
  1  4  1  1
  5  7  3  0
  6  3  2  0
  7 12  1  0
  8  2  1  0
  1  9  1  6
 10  6  1  0
 11  4  2  0
 12 18  2  0
 13  4  1  0
 14  9  1  0
 15 14  1  0
  8 16  1  1
 10 17  1  6
 18 21  1  0
 19 20  2  0
 20 15  1  0
 21 15  2  0
 10  8  1  0
 19 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA351107

   (1R,4R,5R)-1-(4-Cyano-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: 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: 3.07

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: -2.84

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: 0.69

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