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

ID: ALA4741430

PubChem CID: 161978962

Max Phase: Preclinical

Molecular Formula: C6H8BrNO2

Molecular Weight: 206.04

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H8BrNO2/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:  YPJWGPZLYRDOAE-WHFBIAKZSA-N

Molfile:  

 
     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
   30.7831   -3.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6081   -3.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8650   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1956   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5306   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7459   -2.6321    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   30.2973   -4.3376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6499   -2.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2623   -3.1857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8225   -1.8262    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:

   

   ALA4741430

   ---

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: 206.04

Molecular Weight (Monoisotopic): 204.9738

AlogP: 0.49

#Rotatable Bonds: 1

Polar Surface Area: 63.32

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.10

CX Basic pKa: 8.32

CX LogP: -1.84

CX LogD: -1.89

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.61

Np Likeness Score: 1.55

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