nicotinoylalanine (NAL)

ID: ALA160527

Cas Number: 137548-54-0

PubChem CID: 126254

Max Phase: Preclinical

Molecular Formula: C9H10N2O3

Molecular Weight: 194.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nicotinoylalanine | 137548-54-0|alpha-Amino-gamma-oxo-3-pyridinebutanoic acid|2-amino-4-oxo-4-pyridin-3-ylbutanoic acid|CHEMBL160527|nicotylalanine|SCHEMBL8439392|DTXSID00929823|2-AMINO-4-OXO-4-(PYRIDIN-3-YL)BUTANOIC ACID|3-Pyridinebutanoic acid, alpha-amino-gamma-oxo-, (+-)-

Canonical SMILES:  NC(CC(=O)c1cccnc1)C(=O)O

Standard InChI:  InChI=1S/C9H10N2O3/c10-7(9(13)14)4-8(12)6-2-1-3-11-5-6/h1-3,5,7H,4,10H2,(H,13,14)

Standard InChI Key:  BOOQPWXVCDYIJP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    7.1667   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792   -0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -1.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9000    0.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125    0.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -0.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -1.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  2  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8  3  2  0
  9  1  2  0
 10 11  2  0
 11  5  1  0
 12  5  2  0
 13 14  2  0
 14 12  1  0
 10 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA160527

   NICOTINOYLALANINENAL

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: 194.19

Molecular Weight (Monoisotopic): 194.0691

AlogP: 0.07

#Rotatable Bonds: 4

Polar Surface Area: 93.28

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.39

CX Basic pKa: 8.96

CX LogP: -2.95

CX LogD: -2.96

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.66

Np Likeness Score: 0.00

References

1. Pellicciari R, Natalini B, Costantino G, Mahmoud MR, Mattoli L, Sadeghpour BM, Moroni F, Chiarugi A, Carpenedo R..  (1994)  Modulation of the kynurenine pathway in search for new neuroprotective agents. Synthesis and preliminary evaluation of (m-nitrobenzoyl)alanine, a potent inhibitor of kynurenine-3-hydroxylase.,  37  (5): [PMID:8126705] [10.1021/jm00031a015]

Source

Source(1):

• Scientific Literature