(S)-5-amino-2-(5-hydroxy-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid

ID: ALA1939688

PubChem CID: 38988887

Max Phase: Preclinical

Molecular Formula: C13H12N2O6

Molecular Weight: 292.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-78623 | NSC-78623|CHEMBL1939688

Canonical SMILES:  NC(=O)CC[C@@H](C(=O)O)N1C(=O)c2ccc(O)cc2C1=O

Standard InChI:  InChI=1S/C13H12N2O6/c14-10(17)4-3-9(13(20)21)15-11(18)7-2-1-6(16)5-8(7)12(15)19/h1-2,5,9,16H,3-4H2,(H2,14,17)(H,20,21)/t9-/m0/s1

Standard InChI Key:  OMADFDXNAFQWOZ-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    7.9607  -25.9948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462  -25.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5317  -25.9948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462  -24.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607  -24.3448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0469  -23.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338  -22.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539  -23.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2664  -22.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914  -22.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5039  -23.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289  -23.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914  -24.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2664  -24.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7143  -24.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8859  -25.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5317  -24.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8173  -24.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028  -24.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028  -23.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883  -24.7573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  8 14  1  0
 14 15  1  0
  5 15  1  0
 15 16  2  0
  4 17  1  6
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1939688

   (2S)-5-amino-2-(5-hydroxy-1,3-dioxoisoindol-2-yl)-5-oxopentanoic 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: 292.25

Molecular Weight (Monoisotopic): 292.0695

AlogP: -0.29

#Rotatable Bonds: 5

Polar Surface Area: 138.00

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.96

CX Basic pKa: ┄

CX LogP: -0.50

CX LogD: -4.13

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.64

Np Likeness Score: -0.07

References

1. Wang Y, Hess TN, Jones V, Zhou JZ, McNeil MR, Andrew McCammon J..  (2011)  Novel inhibitors of Mycobacterium tuberculosis dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD) identified by virtual screening.,  21  (23): [PMID:22014548] [10.1016/j.bmcl.2011.09.094]

Source

Source(1):

• Scientific Literature