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

ID: ALA3969063

PubChem CID: 67705089

Max Phase: Preclinical

Molecular Formula: C17H16Cl2N4O5S

Molecular Weight: 459.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@]1(C(=O)O)[C@@H]2[C@@H](C(=O)O)[C@@H]2[C@H](Sc2nc[nH]n2)[C@H]1OCc1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C17H16Cl2N4O5S/c18-7-2-1-6(3-8(7)19)4-28-13-12(29-16-21-5-22-23-16)9-10(14(24)25)11(9)17(13,20)15(26)27/h1-3,5,9-13H,4,20H2,(H,24,25)(H,26,27)(H,21,22,23)/t9-,10-,11-,12-,13+,17+/m0/s1

Standard InChI Key:  QHBLXVIRCXAIGL-WNAOHANSSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.9062  -16.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324  -16.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154  -16.8578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256  -15.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543  -14.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603  -15.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759  -14.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591  -15.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421  -15.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6471  -14.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201  -16.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188  -13.9754    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426  -15.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631  -14.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8802  -14.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970  -16.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6892  -17.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737  -14.1703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485  -16.6217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2746  -15.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0909  -15.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122  -14.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1113  -14.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962  -14.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292  -13.3569    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3293  -14.7887    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0814  -13.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605  -12.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5592  -12.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435  -12.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644  -13.4303    0.0000 N   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  6
  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
 23 25  1  0
 22 26  1  0
 12 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3969063

   (1R,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorophenyl)methoxy]-4-(1H-1,2,4-triazol-5-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

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

Calculated Properties

Molecular Weight: 459.31

Molecular Weight (Monoisotopic): 458.0218

AlogP: 1.90

#Rotatable Bonds: 7

Polar Surface Area: 151.42

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.58

CX Basic pKa: 10.36

CX LogP: -0.37

CX LogD: -3.63

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.21

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

Source(1):

• Scientific Literature