ID: ALA2381643

Max Phase: Preclinical

Molecular Formula: C8H11NO5

Molecular Weight: 201.18

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C8H11NO5/c9-8(7(13)14)1-2(10)3-4(5(3)8)6(11)12/h2-5,10H,1,9H2,(H,11,12)(H,13,14)/t2-,3-,4-,5-,8-/m0/s1

Standard InChI Key:  XMDLTKGXRPVDSY-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: 201.18

Molecular Weight (Monoisotopic): 201.0637

AlogP: -1.52

#Rotatable Bonds: 2

Polar Surface Area: 120.85

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.68

CX Basic pKa: 9.50

CX LogP: -4.30

CX LogD: -7.41

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.43

Np Likeness Score: 1.55

References

1. Monn JA, Valli MJ, Massey SM, Hao J, Reinhard MR, Bures MG, Heinz BA, Wang X, Carter JH, Getman BG, Stephenson GA, Herin M, Catlow JT, Swanson S, Johnson BG, McKinzie DL, Henry SS..  (2013)  Synthesis and pharmacological characterization of 4-substituted-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylates: identification of new potent and selective metabotropic glutamate 2/3 receptor agonists.,  56  (11): [PMID:23675965] [10.1021/jm4000165]

2. Dressman BA, Tromiczak EG, Chappell MD, Tripp AE, Quimby SJ, Vetman T, Fivush AM, Matt J, Jaramillo C, Li R, Khilevich A, Blanco MJ, Smith SC, Carpintero M, de Diego JE, Barberis M, García-Cerrada S, Soriano JF, Schkeryantz JM, Witkin JM, Wafford KA, Seidel W, Britton T, Overshiner CD, Li X, Wang XS, Heinz BA, Catlow JT, Swanson S, Bedwell D, Ornstein PL, Mitch CH..  (2016)  Novel bicyclo[3.1.0]hexane analogs as antagonists of metabotropic glutamate 2/3 receptors for the treatment of depression.,  26  (23): [PMID:27836401] [10.1016/j.bmcl.2016.10.067]

3. Chappell MD,Li R,Smith SC,Dressman BA,Tromiczak EG,Tripp AE,Blanco MJ,Vetman T,Quimby SJ,Matt J,Britton TC,Fivush AM,Schkeryantz JM,Mayhugh D,Erickson JA,Bures MG,Jaramillo C,Carpintero M,Diego JE,Barberis M,Garcia-Cerrada S,Soriano JF,Antonysamy S,Atwell S,MacEwan I,Condon B,Sougias C,Wang J,Zhang A,Conners K,Groshong C,Wasserman SR,Koss JW,Witkin JM,Li X,Overshiner C,Wafford KA,Seidel W,Wang XS,Heinz BA,Swanson S,Catlow JT,Bedwell DW,Monn JA,Mitch CH,Ornstein PL.  (2016)  Discovery of (1S,2R,3S,4S,5R,6R)-2-Amino-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic Acid Hydrochloride (LY3020371·HCl): A Potent, Metabotropic Glutamate 2/3 Receptor Antagonist with Antidepressant-Like Activity.,  59  (24.0): [PMID:28002967] [10.1021/acs.jmedchem.6b01119]

Source

Source(1):

• Scientific Literature