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

ID: ALA4747359

PubChem CID: 157378005

Max Phase: Preclinical

Molecular Formula: C6H8FNO2

Molecular Weight: 145.13

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H8FNO2/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:  BKNQWWQSPJIUPN-WHFBIAKZSA-N

Molfile:  

 
     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
   12.6043   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4293   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6861   -2.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0168   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3518   -2.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5670   -2.4072    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.1185   -4.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4711   -2.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0835   -2.9608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6438   -1.6012    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:

   

   ALA4747359

   ---

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: 145.13

Molecular Weight (Monoisotopic): 145.0539

AlogP: 0.07

#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: 3.96

CX Basic pKa: 8.62

CX LogP: -2.49

CX LogD: -2.51

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.55

Np Likeness Score: 1.18

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