5-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)pentyl 4-chlorophenylcarbamate

ID: ALA2385320

PubChem CID: 71660228

Max Phase: Preclinical

Molecular Formula: C24H31ClN2O4

Molecular Weight: 446.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(CCCCCOC(=O)Nc1ccc(Cl)cc1)N(C)CC2

Standard InChI:  InChI=1S/C24H31ClN2O4/c1-27-13-12-17-15-22(29-2)23(30-3)16-20(17)21(27)7-5-4-6-14-31-24(28)26-19-10-8-18(25)9-11-19/h8-11,15-16,21H,4-7,12-14H2,1-3H3,(H,26,28)

Standard InChI Key:  XDUGUNUQOCQISM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.3635   -2.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3624   -3.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0772   -3.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0754   -1.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7908   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7942   -3.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5134   -3.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2338   -3.0150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2303   -2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5065   -1.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5156   -4.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8023   -4.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8045   -5.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0912   -5.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9493   -3.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6490   -1.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6488   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6476   -3.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9334   -3.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0934   -6.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3801   -7.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6645   -6.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6622   -5.9150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9511   -7.1544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2355   -6.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2358   -5.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5211   -5.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8068   -5.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8117   -6.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5270   -7.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906   -5.5146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
  1 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385320

   5-(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)pentyl N-(4-chlorophenyl)carbamate

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: 446.98

Molecular Weight (Monoisotopic): 446.1972

AlogP: 5.70

#Rotatable Bonds: 9

Polar Surface Area: 60.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.03

CX Basic pKa: 8.31

CX LogP: 5.43

CX LogD: 4.47

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -0.09

References

1. Galán A, Moreno L, Párraga J, Serrano Á, Sanz MJ, Cortes D, Cabedo N..  (2013)  Novel isoquinoline derivatives as antimicrobial agents.,  21  (11): [PMID:23601815] [10.1016/j.bmc.2013.03.042]

Source

Source(1):

• Scientific Literature