(E)-(1R,2S)-1-((S)-2-amino-2-carboxyethyl)cyclopropane-1,2-dicarboxylic acid

ID: ALA3787264

PubChem CID: 127030385

Max Phase: Preclinical

Molecular Formula: C8H11NO6

Molecular Weight: 217.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](C[C@]1(C(=O)O)C[C@@H]1C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C8H11NO6/c9-4(6(12)13)2-8(7(14)15)1-3(8)5(10)11/h3-4H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15)/t3-,4+,8-/m1/s1

Standard InChI Key:  BHSHZTNHTMTQFY-PDJPSNROSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.0668    1.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    0.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3663    2.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4055    1.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667    3.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276    2.4090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728   -2.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055   -2.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055   -0.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -0.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.4329    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 13  1  0
  1  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  1
 13  7  1  1
  7  8  1  0
  7  9  2  0
 14 10  1  0
 10 11  1  0
 10 12  2  0
 14 13  1  0
 14 15  1  0
 13 15  1  0
 14 16  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3787264

   ---

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: 217.18

Molecular Weight (Monoisotopic): 217.0586

AlogP: -1.04

#Rotatable Bonds: 5

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: 1.61

CX Basic pKa: 9.52

CX LogP: -3.37

CX LogD: -8.38

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.46

Np Likeness Score: 1.45

References

1. 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