ethyl (2S)-3-hydroxy-2-[(4-hydroxybenzoyl)amino]propanoate

ID: ALA5282083

Max Phase: Preclinical

Molecular Formula: C12H15NO5

Molecular Weight: 253.25

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](CO)NC(=O)c1ccc(O)cc1

Standard InChI:  InChI=1S/C12H15NO5/c1-2-18-12(17)10(7-14)13-11(16)8-3-5-9(15)6-4-8/h3-6,10,14-15H,2,7H2,1H3,(H,13,16)/t10-/m0/s1

Standard InChI Key:  KBDZQSUJSRRLAK-JTQLQIEISA-N

Molfile:  

 
     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.8571    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.2064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425   -0.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
 10  8  1  6
 10 11  1  0
 10 12  1  0
 12 13  1  0
 11 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282083

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 253.25

Molecular Weight (Monoisotopic): 253.0950

AlogP: 0.05

#Rotatable Bonds: 5

Polar Surface Area: 95.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: ┄

CX LogP: 0.25

CX LogD: 0.21

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: -0.11

References

1. Ju Z, Shang Z, Mahmud T, Fang J, Liu Y, Pan Q, Lin X, Chen F..  (2023)  Synthesis and Anti-Inflammatory Activity of the Natural Cyclooxygenase-2 Inhibitor Axinelline A and Its Analogues.,  86  (4): [PMID:36880830] [10.1021/acs.jnatprod.2c01153]

Source

Source(1):

• Scientific Literature