(2S,4S)-4-(2-Hydroxy-2-oxoethyl)glutamic Acid

ID: ALA479797

Chembl Id: CHEMBL479797

PubChem CID: 24905703

Max Phase: Preclinical

Molecular Formula: C7H11NO6

Molecular Weight: 205.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](C[C@@H](CC(=O)O)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C7H11NO6/c8-4(7(13)14)1-3(6(11)12)2-5(9)10/h3-4H,1-2,8H2,(H,9,10)(H,11,12)(H,13,14)/t3-,4-/m0/s1

Standard InChI Key:  QUHCPZVRCOASQB-IMJSIDKUSA-N

Alternative Forms

1. Parent:

   

   ALA479797

   (2S,4S)-4-(2-Hydroxy-2-oxoethyl)glutamic 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: 205.17

Molecular Weight (Monoisotopic): 205.0586

AlogP: -1.04

#Rotatable Bonds: 6

Polar Surface Area: 137.92

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.65

CX Basic pKa: 9.53

CX LogP: -3.59

CX LogD: -8.68

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.43

Np Likeness Score: 0.87

References

1. Sagot E, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Chapelet M, Bolte J, Gefflaut T, Bunch L..  (2008)  Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7.,  51  (14): [PMID:18578478] [10.1021/jm800092x]

2. Sagot E, Jensen AA, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Assaf Z, Aboab B, Bolte J, Gefflaut T, Bunch L..  (2008)  Chemo-enzymatic synthesis of (2S,4R)-2-amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic acid: a novel selective inhibitor of human excitatory amino acid transporter subtype 2.,  51  (14): [PMID:18578477] [10.1021/jm800091e]

3. Huynh TH, Erichsen MN, Tora AS, Goudet C, Sagot E, Assaf Z, Thomsen C, Brodbeck R, Stensbøl TB, Bjørn-Yoshimoto WE, Nielsen B, Pin JP, Gefflaut T, Bunch L..  (2016)  New 4-Functionalized Glutamate Analogues Are Selective Agonists at Metabotropic Glutamate Receptor Subtype 2 or Selective Agonists at Metabotropic Glutamate Receptor Group III.,  59  (3): [PMID:26814576] [10.1021/acs.jmedchem.5b01333]

Source

Source(1):

• Scientific Literature