2-aminoN-hydroxy-3-(1H-indol-3-yl)-propionimidic acid

ID: ALA490034

Chembl Id: CHEMBL490034

PubChem CID: 667595

Max Phase: Preclinical

Molecular Formula: C11H13N3O2

Molecular Weight: 219.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NO

Standard InChI:  InChI=1S/C11H13N3O2/c12-9(11(15)14-16)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13,16H,5,12H2,(H,14,15)/t9-/m0/s1

Standard InChI Key:  LBMAEBPZXXNKMZ-VIFPVBQESA-N

Alternative Forms

1. Parent:

   

   ALA490034

   N-Hydroxy-L-tryptophanamide

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: 219.24

Molecular Weight (Monoisotopic): 219.1008

AlogP: 0.54

#Rotatable Bonds: 3

Polar Surface Area: 91.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.79

CX Basic pKa: 7.53

CX LogP: 0.13

CX LogD: -0.07

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.45

Np Likeness Score: 0.09

References

1. Ramsden NL, Buetow L, Dawson A, Kemp LA, Ulaganathan V, Brenk R, Klebe G, Hunter WN..  (2009)  A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.,  52  (8): [PMID:19320487] [10.1021/jm801475n]

2. Zur AA,Chien HC,Augustyn E,Flint A,Heeren N,Finke K,Hernandez C,Hansen L,Miller S,Lin L,Giacomini KM,Colas C,Schlessinger A,Thomas AA.  (2016)  LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates.,  26  (20.0): [PMID:27624080] [10.1016/j.bmcl.2016.09.001]

3. Blain JM, Grote DL, Watkins SM, Goshu GM, Muller C, Gorman JL, Ranieri G, Walter RL, Hofstetter H, Horn JR, Hagen TJ..  (2021)  Structural and biophysical characterization of the Burkholderia pseudomallei IspF inhibitor L-tryptophan hydroxamate.,  48  [PMID:34298132] [10.1016/j.bmcl.2021.128273]

Source

Source(1):

• Scientific Literature