(-)-(R)-1-(2-(2,3-dichlorophenoxy)-1-phenylethyl)-4-methylpiperazine Oxalate

ID: ALA2260933

PubChem CID: 76326515

Max Phase: Preclinical

Molecular Formula: C21H24Cl2N2O5

Molecular Weight: 365.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN([C@@H](COc2cccc(Cl)c2Cl)c2ccccc2)CC1.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C19H22Cl2N2O.C2H2O4/c1-22-10-12-23(13-11-22)17(15-6-3-2-4-7-15)14-24-18-9-5-8-16(20)19(18)21;3-1(4)2(5)6/h2-9,17H,10-14H2,1H3;(H,3,4)(H,5,6)/t17-;/m0./s1

Standard InChI Key:  WLPOPQWAXLIJCV-LMOVPXPDSA-N

Molfile:  

     RDKit          2D

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   22.7623  -20.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4758  -20.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0519  -20.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7623  -19.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1822  -20.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4758  -21.3129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6576  -22.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9435  -21.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2253  -22.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5113  -21.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7973  -22.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7973  -22.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0834  -23.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3652  -22.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3652  -22.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0834  -21.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0844  -20.7948    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.9421  -20.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6593  -20.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6607  -19.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9456  -19.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2276  -19.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2298  -20.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6506  -21.6198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.6510  -22.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3608  -23.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0778  -22.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0802  -22.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3657  -21.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7910  -23.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  2  5  2  0
  2  6  1  0
  8  9  1  0
  7  8  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 10 11  1  0
  9 10  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  8 18  1  1
 15 24  1  0
  7 25  1  0
  7 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
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: 365.30

Molecular Weight (Monoisotopic): 364.1109

AlogP: 4.36

#Rotatable Bonds: 5

Polar Surface Area: 15.71

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.52

CX LogP: 4.67

CX LogD: 4.31

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -1.28

References

1. Ismaiel AM, Gad LM, Ghareib SA, Bamanie FH, Moustafa MA.  (2009)  Synthesis of aryloxyalkylamines as h5-HT1B agonists with potential analgesic activity,  18  (9): [10.1007/s00044-009-9164-1]

Source

Source(1):

• Scientific Literature