(2S,4R)-4-(3-Oxo-3-tert-butoxyaminopropyl)glutamic Acid

ID: ALA2312401

PubChem CID: 71574833

Max Phase: Preclinical

Molecular Formula: C12H22N2O6

Molecular Weight: 290.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H22N2O6/c1-12(2,3)20-14-9(15)5-4-7(10(16)17)6-8(13)11(18)19/h7-8H,4-6,13H2,1-3H3,(H,14,15)(H,16,17)(H,18,19)/t7-,8+/m1/s1

Standard InChI Key:  ZVLQXZKBRAEEDB-SFYZADRCSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
    3.7393  -10.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470  -10.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316  -10.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393  -11.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316   -9.2285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239  -10.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -10.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624  -10.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5701  -10.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624   -9.2285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -11.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624  -11.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624  -12.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5701  -12.9058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -12.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2778  -12.4972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9855  -12.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6932  -12.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9855  -13.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6878  -13.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  6
  3  5  2  0
  3  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2312401

   (2S,4R)-2-amino-4-[3-[(2-methylpropan-2-yl)oxyamino]-3-oxopropyl]pentanedioic 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: 290.32

Molecular Weight (Monoisotopic): 290.1478

AlogP: 0.12

#Rotatable Bonds: 8

Polar Surface Area: 138.95

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.69

CX Basic pKa: 9.56

CX LogP: -2.50

CX LogD: -5.42

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: 0.45

References

1. Assaf Z, Larsen AP, Venskutonytė R, Han L, Abrahamsen B, Nielsen B, Gajhede M, Kastrup JS, Jensen AA, Pickering DS, Frydenvang K, Gefflaut T, Bunch L..  (2013)  Chemoenzymatic synthesis of new 2,4-syn-functionalized (S)-glutamate analogues and structure-activity relationship studies at ionotropic glutamate receptors and excitatory amino acid transporters.,  56  (4): [PMID:23414088] [10.1021/jm301433m]

Source

Source(1):

• Scientific Literature