2beta-carbo-2'-[18F]fluoroethoxy-3beta-(4-bromo-phenyl)tropane

ID: ALA393600

PubChem CID: 44429580

Max Phase: Preclinical

Molecular Formula: C17H21BrFNO2

Molecular Weight: 370.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MCL-322 | CHEMBL393600|MCL-322

Canonical SMILES:  CN1C2CCC1C(C(=O)OCC[18F])C(c1ccc(Br)cc1)C2

Standard InChI:  InChI=1S/C17H21BrFNO2/c1-20-13-6-7-15(20)16(17(21)22-9-8-19)14(10-13)11-2-4-12(18)5-3-11/h2-5,13-16H,6-10H2,1H3/i19-1

Standard InChI Key:  LEEXJBMYTWENTA-AWDFDDCISA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.9539    0.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479    1.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443    0.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9318   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -0.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -0.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -0.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4668    0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6342    0.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220    1.6942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432    1.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758    0.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533    1.3598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649    1.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6948   -1.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189    0.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -0.5821    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0
  9 11  2  0
  1  4  1  0
 10 12  1  0
  3  5  1  0
 12 13  1  0
  4  6  1  0
 13 14  1  0
  5  8  1  0
  2 15  1  0
  7  6  1  0
  5 16  1  0
  7  8  1  0
 16 17  2  0
  7  2  1  0
 17 18  1  0
 18 19  2  0
  3  9  1  0
 19 20  1  0
  1  2  1  0
 20 21  2  0
 21 16  1  0
  9 10  1  0
 19 22  1  0
M  ISO  1  14  18
M  END

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: 370.26

Molecular Weight (Monoisotopic): 369.0740

AlogP: 3.53

#Rotatable Bonds: 4

Polar Surface Area: 29.54

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.12

CX LogP: 3.48

CX LogD: 1.76

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.14

References

1. Wuest F, Berndt M, Strobel K, van den Hoff J, Peng X, Neumeyer JL, Bergmann R..  (2007)  Synthesis and radiopharmacological characterization of 2beta-carbo-2'-[18F]fluoroethoxy-3beta-(4-bromo-phenyl)tropane ([18F]MCL-322) as a PET radiotracer for imaging the dopamine transporter (DAT).,  15  (13): [PMID:17467995] [10.1016/j.bmc.2007.04.019]

Source

Source(1):

• Scientific Literature