ID: ALA334014

Max Phase: Preclinical

Molecular Formula: C8H10FNO4

Molecular Weight: 203.17

Molecule Type: Small molecule

Representations

Canonical SMILES:  N[C@]1(C(=O)O)[C@H]2[C@@H](C[C@@H]1F)[C@@H]2C(=O)O

Standard InChI:  InChI=1S/C8H10FNO4/c9-3-1-2-4(6(11)12)5(2)8(3,10)7(13)14/h2-5H,1,10H2,(H,11,12)(H,13,14)/t2-,3-,4-,5-,8-/m0/s1

Standard InChI Key:  DIWVNJFXRKZAGI-FJNNMDBYSA-N

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

Properties

Molecular Weight: 203.17

Molecular Weight (Monoisotopic): 203.0594

AlogP: -0.54

#Rotatable Bonds: 2

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.83

CX Basic pKa: 8.72

CX LogP: -3.09

CX LogD: -6.12

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.56

Np Likeness Score: 0.94

References

1. Collado I, Pedregal C, Mazón A, Espinosa JF, Blanco-Urgoiti J, Schoepp DD, Wright RA, Johnson BG, Kingston AE..  (2002)  (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-methylcyclopropyl) glycine is a potent and selective metabotropic group 2 receptor agonist with anxiolytic properties.,  45  (17): [PMID:12166935] [10.1021/jm0110486]

2. Nakazato A, Kumagai T, Sakagami K, Yoshikawa R, Suzuki Y, Chaki S, Ito H, Taguchi T, Nakanishi S, Okuyama S..  (2000)  Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists.,  43  (25): [PMID:11123999] [10.1021/jm000346k]

3. Nakazato A, Kumagai T, Sakagami K, Yoshikawa R, Suzuki Y, Chaki S, Ito H, Taguchi T, Nakanishi S, Okuyama S..  (2000)  Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists.,  43  (25): [PMID:11123999] [10.1021/jm000346k]

4. Nakazato A, Kumagai T, Sakagami K, Yoshikawa R, Suzuki Y, Chaki S, Ito H, Taguchi T, Nakanishi S, Okuyama S..  (2000)  Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists.,  43  (25): [PMID:11123999] [10.1021/jm000346k]

5. Urabe H,Miyakoshi N,Ohtake N,Nozoe A,Ochi M,Fukasawa M,Kinoshita K,Yamaguchi JI,Marumo T,Hikichi H,Chaki S,Hashihayata T.  (2020)  Discovery of MGS0274, an ester prodrug of a metabotropic glutamate receptor 2/3 agonist with improved oral bioavailability.,  203  [PMID:32698110] [10.1016/j.ejmech.2020.112521]

Source

Source(1):

• Scientific Literature