[11C]-1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine

ID: ALA2311153

Cas Number: 305367-64-0

PubChem CID: 9820591

Max Phase: Preclinical

Molecular Formula: C23H32N2O2

Molecular Weight: 368.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: [11C]SA-4503 | Cutamesine C-11|UNII-E5PN36ILY5|E5PN36ILY5|CHEMBL2311153|SA-4503 C-11|(11C)SA4503|[11C]SA4503|305367-64-0|1-(2-(3-Methoxy-4-(methoxy-11C)phenyl)ethyl)-4-(3-phenylpropyl)piperazine|[11C]SA-4503|1-([4-methoxy-11C]-3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine|1-[2-(3-Methoxy-4-(111C)methoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine

Canonical SMILES:  COc1cc(CCN2CCN(CCCc3ccccc3)CC2)ccc1O[11CH3]

Standard InChI:  InChI=1S/C23H32N2O2/c1-26-22-11-10-21(19-23(22)27-2)12-14-25-17-15-24(16-18-25)13-6-9-20-7-4-3-5-8-20/h3-5,7-8,10-11,19H,6,9,12-18H2,1-2H3/i1-1

Standard InChI Key:  UVSWWUWQVAQPJR-BJUDXGSMSA-N

Molfile:  

     RDKit          2D

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   -4.1412   -6.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -7.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -7.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4893   -6.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -6.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321   -6.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9662   -6.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -6.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1397   -8.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647   -8.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -6.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -7.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -7.5873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -8.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8076   -8.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2219   -7.5845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8085   -6.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191   -6.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469   -7.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2850   -6.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981   -6.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206   -6.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337   -5.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -4.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -4.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2832   -5.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  2  2  0
  1  7  1  0
  3  4  2  0
  7  8  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  2  9  1  0
 16 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
  4 11  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
M  ISO  1   8  11
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: 368.52

Molecular Weight (Monoisotopic): 368.2464

AlogP: 3.50

#Rotatable Bonds: 9

Polar Surface Area: 24.94

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.33

CX LogP: 4.19

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.55

References

1. Li ZJ, Ren HY, Cui MC, Deuther-Conrad W, Tang RK, Steinbach J, Brust P, Liu BL, Jia HM..  (2011)  Synthesis and biological evaluation of novel 4-benzylpiperazine ligands for sigma-1 receptor imaging.,  19  (9): [PMID:21481592] [10.1016/j.bmc.2011.03.037]

2. Maisonial A, Grosse Maestrup E, Wiese C, Hiller A, Schepmann D, Fischer S, Deuther-Conrad W, Steinbach J, Brust P, Wünsch B..  (2012)  Synthesis, radiofluorination and pharmacological evaluation of a fluoromethyl spirocyclic PET tracer for central σ1 receptors and comparison with fluoroalkyl homologs.,  20  (1): [PMID:22136765] [10.1016/j.bmc.2011.11.002]

3. James ML, Shen B, Zavaleta CL, Nielsen CH, Mesangeau C, Vuppala PK, Chan C, Avery BA, Fishback JA, Matsumoto RR, Gambhir SS, McCurdy CR, Chin FT..  (2012)  New positron emission tomography (PET) radioligand for imaging σ-1 receptors in living subjects.,  55  (19): [PMID:22853801] [10.1021/jm300371c]

4. Li Y, Wang X, Zhang J, Deuther-Conrad W, Xie F, Zhang X, Liu J, Qiao J, Cui M, Steinbach J, Brust P, Liu B, Jia H..  (2013)  Synthesis and evaluation of novel (18)F-labeled spirocyclic piperidine derivatives as σ1 receptor ligands for positron emission tomography imaging.,  56  (9): [PMID:23566245] [10.1021/jm301734g]

Source

Source(1):

• Scientific Literature