(3S,4S)-3-Amino-4-chlorocyclopent-1-enecarboxylic acid

ID: ALA4758952

PubChem CID: 159108705

Max Phase: Preclinical

Molecular Formula: C6H8ClNO2

Molecular Weight: 161.59

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H8ClNO2/c7-4-1-3(6(9)10)2-5(4)8/h2,4-5H,1,8H2,(H,9,10)/t4-,5-/m0/s1

Standard InChI Key:  KEFDDAGGJVNDFS-WHFBIAKZSA-N

Molfile:  

 
     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
   21.3707   -3.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1957   -3.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4525   -2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7832   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1182   -2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3335   -2.5571    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.8849   -4.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2374   -2.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8498   -3.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4101   -1.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  1
  1  7  1  6
  3  8  1  0
  8  9  1  0
  8 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4758952

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 161.59

Molecular Weight (Monoisotopic): 161.0244

AlogP: 0.34

#Rotatable Bonds: 1

Polar Surface Area: 63.32

Molecular Species: ZWITTERION

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.72

CX Basic pKa: 8.82

CX LogP: -2.03

CX LogD: -2.04

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.55

Np Likeness Score: 1.53

References

1. Shen S,Doubleday PF,Weerawarna PM,Zhu W,Kelleher NL,Silverman RB.  (2020)  Mechanism-Based Design of 3-Amino-4-Halocyclopentenecarboxylic Acids as Inactivators of GABA Aminotransferase.,  11  (10): [PMID:33062178] [10.1021/acsmedchemlett.9b00672]

Source

Source(1):

• Scientific Literature