(1S,2R,3S,4R,5R,6R)-2-amino-3-(2,5-dichlorobenzyloxy)-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

ID: ALA3979475

PubChem CID: 134152341

Max Phase: Preclinical

Molecular Formula: C15H15Cl2NO6

Molecular Weight: 376.19

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N[C@]1(C(=O)O)[C@@H]2[C@@H](C(=O)O)[C@@H]2[C@@H](O)[C@H]1OCc1cc(Cl)ccc1Cl

Standard InChI:  InChI=1S/C15H15Cl2NO6/c16-6-1-2-7(17)5(3-6)4-24-12-11(19)8-9(13(20)21)10(8)15(12,18)14(22)23/h1-3,8-12,19H,4,18H2,(H,20,21)(H,22,23)/t8-,9-,10-,11+,12+,15+/m0/s1

Standard InChI Key:  SGCNJDYPITVHEN-AFJGUQMISA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.8893   -9.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3115   -8.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1000   -9.7867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8002   -8.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3243   -7.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5376   -8.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5476   -7.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8336   -8.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0164   -8.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6165   -7.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5993   -9.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5834   -6.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6173   -8.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0329   -7.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8501   -7.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6787   -9.3637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6778  -10.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5397   -7.1030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5315   -9.5545    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2495   -8.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659   -8.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4823   -7.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0764   -6.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613   -6.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8324   -9.0729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.4895   -6.2553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  6  2  1  0
  2  4  1  0
  4  5  1  0
  5  7  1  0
  7  6  1  0
  8  7  1  0
  6  8  1  0
  8  9  1  1
  9 10  2  0
  9 11  1  0
  5 12  1  1
  4 13  1  1
 13 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  2  0
  7 18  1  1
  6 19  1  1
 15 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 15  1  0
 20 25  1  0
 23 26  1  0
M  END

Alternative Forms

  1. Parent:

    ALA3979475

    ---

Associated Targets(Human)

GRM3 Tchem Metabotropic glutamate receptor 3 (732 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRM2 Tchem Metabotropic glutamate receptor 2 (3206 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 376.19Molecular Weight (Monoisotopic): 375.0276AlogP: 0.98#Rotatable Bonds: 5
Polar Surface Area: 130.08Molecular Species: ZWITTERIONHBA: 5HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 1.60CX Basic pKa: 8.87CX LogP: -1.44CX LogD: -4.66
Aromatic Rings: 1Heavy Atoms: 24QED Weighted: 0.60Np Likeness Score: 0.34

References

1. 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]

Source