3-OH-DL-Kynurenine

ID: ALA442576

Cas Number: 2147-61-7

PubChem CID: 89

Product Number: H168592, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H12N2O4

Molecular Weight: 224.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(O)cccc1C(=O)CC(N)C(=O)O

Standard InChI:  InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)

Standard InChI Key:  VCKPUUFAIGNJHC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    8.8179   -0.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1062   -0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3904   -0.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8179   -1.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5338   -0.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.5443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -0.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469   -0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311   -0.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469   -1.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469    0.5443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1062    0.5443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168   -0.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  4  7  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  9 14  1  0
  4  8  1  0
  2 15  1  0
 10 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA442576

   3-Hydroxy-DL-kynurenine

Molecule Features

Natural Product: Yes

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: 224.22

Molecular Weight (Monoisotopic): 224.0797

AlogP: -0.04

#Rotatable Bonds: 4

Polar Surface Area: 126.64

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.99

CX Basic pKa: 8.90

CX LogP: -2.21

CX LogD: -2.22

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.32

Np Likeness Score: 0.94

References

1. Lima S, Kumar S, Gawandi V, Momany C, Phillips RS..  (2009)  Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.,  52  (2): [PMID:19143568] [10.1021/jm8010806]

2. Unpublished dataset, 

3.  (2014)  D-serine transporter inhibitors as pharmaceutical compositions for the treatment of central nervous system disorders, 

4. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(4):

• Scientific Literature
• Gene Expression Atlas Compounds
• Patent Bioactivity Data
• IMI-CARE SARS-CoV-2 Data