(+/-)-3-(((S*)-5-((S*)-Amino(carboxy)methyl)-3-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)methyl)benzoic acid

ID: ALA3121411

PubChem CID: 76318010

Max Phase: Preclinical

Molecular Formula: C13H15N3O5

Molecular Weight: 293.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)[C@@H]1CC(O)=NN1Cc1cccc(C(=O)O)c1

Standard InChI:  InChI=1S/C13H15N3O5/c14-11(13(20)21)9-5-10(17)15-16(9)6-7-2-1-3-8(4-7)12(18)19/h1-4,9,11H,5-6,14H2,(H,15,17)(H,18,19)(H,20,21)/t9-,11-/m0/s1

Standard InChI Key:  UNJOIZKVPFDMNZ-ONGXEEELSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    4.2204  -13.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9836  -13.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6611  -14.3273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204  -13.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0440  -13.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7210  -12.4092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1449  -13.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5321  -14.5827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5823  -13.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4069  -13.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952  -12.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297  -14.6180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790  -15.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9736  -15.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551  -15.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502  -15.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677  -16.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2960  -16.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980  -16.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270  -15.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096  -14.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214  -15.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  4  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
  9 11  1  0
  4 12  1  6
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3121411

   3-[[(5S)-5-[(S)-amino(carboxy)methyl]-3-oxopyrazolidin-1-yl]methyl]benzoic 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: 293.28

Molecular Weight (Monoisotopic): 293.1012

AlogP: 0.24

#Rotatable Bonds: 5

Polar Surface Area: 136.45

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.57

CX Basic pKa: 8.45

CX LogP: -2.39

CX LogD: -7.73

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: -0.29

References

1. Pinto A, Tamborini L, Mastronardi F, Ettari R, Safoz Y, Bunch L, Nielsen B, Jensen AA, De Micheli C, Conti P..  (2014)  Synthesis of (3-hydroxy-pyrazolin-5-yl)glycine based ligands interacting with ionotropic glutamate receptors.,  75  [PMID:24531228] [10.1016/j.ejmech.2014.01.029]

Source

Source(1):

• Scientific Literature