(+/-)-cis-methyl 2-[(1-adamantylamino)methyl]-1-phenyl-cyclopropanecarboxylate

ID: ALA4740355

PubChem CID: 73117956

Max Phase: Preclinical

Molecular Formula: C22H29NO2

Molecular Weight: 339.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1(c2ccccc2)CC1CNC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C22H29NO2/c1-25-20(24)22(18-5-3-2-4-6-18)13-19(22)14-23-21-10-15-7-16(11-21)9-17(8-15)12-21/h2-6,15-17,19,23H,7-14H2,1H3

Standard InChI Key:  JPCDCMZXHGXNID-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   17.6716   -4.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3129   -4.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4803   -4.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0285   -4.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2371   -4.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7804   -4.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775   -3.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0341   -3.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3084   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7862   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0290   -2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3119   -1.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6001   -2.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7753   -2.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1923   -3.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3581   -1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7690   -0.8971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5331   -1.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5940   -0.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9748   -2.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3936   -1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5937   -2.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3750   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9623   -3.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7600   -3.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 13 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 14 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740355

   Methyl 2-[(1-adamantylamino)methyl]-1-phenylcyclopropane-1-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 339.48

Molecular Weight (Monoisotopic): 339.2198

AlogP: 3.68

#Rotatable Bonds: 5

Polar Surface Area: 38.33

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.22

CX LogP: 3.74

CX LogD: 1.05

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: 0.16

References

1. Schinor B,Hruschka S,Daniliuc CG,Schepmann D,Wünsch B,Haufe G.  (2020)  Fluorinated 2-Arylcyclopropan-1-amines - A new class of sigma receptor ligands.,  28  (22): [PMID:33007549] [10.1016/j.bmc.2020.115726]

2. Schinor B,Hruschka S,Daniliuc CG,Schepmann D,Wünsch B,Haufe G.  (2020)  Fluorinated 2-Arylcyclopropan-1-amines - A new class of sigma receptor ligands.,  28  (22): [PMID:33007549] [10.1016/j.bmc.2020.115726]

Source

Source(1):

• Scientific Literature