(1S,2S,3S,5R,65)-2-amino-3-fluoro-6-(((S)-1-(((((1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyclo[3.1.0]hexane-2-carboxylic acid

ID: ALA4793451

Chembl Id: CHEMBL4793451

PubChem CID: 72550767

Max Phase: Preclinical

Molecular Formula: C21H32FNO7

Molecular Weight: 429.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)O[C@@H](C)OC(=O)[C@H]1[C@@H]2C[C@H](F)[C@@](N)(C(=O)O)[C@@H]21

Standard InChI:  InChI=1S/C21H32FNO7/c1-9(2)12-6-5-10(3)7-14(12)30-20(27)29-11(4)28-18(24)16-13-8-15(22)21(23,17(13)16)19(25)26/h9-17H,5-8,23H2,1-4H3,(H,25,26)/t10-,11+,12+,13+,14-,15+,16+,17+,21+/m1/s1

Standard InChI Key:  IPAZEPBIOFZFEF-UZEWAWMVSA-N

Alternative Forms

1. Parent:

   

   ALA4793451

   (1S,2S,3S,5R,6S)-2-amino-3-fluoro-6-[(1S)-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxycarbonyloxyethoxy]carbonylbicyclo[3.1.0]hexane-2-carboxylic acid

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: 429.49

Molecular Weight (Monoisotopic): 429.2163

AlogP: 2.88

#Rotatable Bonds: 6

Polar Surface Area: 125.15

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.72

CX Basic pKa: 8.69

CX LogP: 0.99

CX LogD: 0.97

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: 1.04

References

1. 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