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

ID: ALA152880

PubChem CID: 11425547

Max Phase: Preclinical

Molecular Formula: C14H16O5

Molecular Weight: 264.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(OCc2ccccc2)C=C[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C14H16O5/c15-11-6-7-14(13(17)18,8-12(11)16)19-9-10-4-2-1-3-5-10/h1-7,11-12,15-16H,8-9H2,(H,17,18)/t11-,12-,14+/m1/s1

Standard InChI Key:  KCSKJSLBJSEGLQ-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    0.9500    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    1.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292    0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.5250    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  3  2  0
  6  2  1  0
  1  7  1  6
  8  5  1  0
  9  4  2  0
 10  4  1  0
 11  7  1  0
  6 12  1  1
  8 13  1  6
 14 11  1  0
 15 14  2  0
 16 14  1  0
 17 15  1  0
 18 16  2  0
 19 18  1  0
  8  6  1  0
 19 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA152880

   (1R,4R,5R)-1-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: 264.28

Molecular Weight (Monoisotopic): 264.0998

AlogP: 0.71

#Rotatable Bonds: 4

Polar Surface Area: 86.99

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.73

CX Basic pKa: ┄

CX LogP: 0.77

CX LogD: -2.52

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.70

Np Likeness Score: 1.25

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