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

ID: ALA2385324

PubChem CID: 71660232

Max Phase: Preclinical

Molecular Formula: C26H35ClN2O4

Molecular Weight: 475.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(CCCCCOC(=O)NCCc1ccc(Cl)cc1)N(C)CC2

Standard InChI:  InChI=1S/C26H35ClN2O4/c1-29-15-13-20-17-24(31-2)25(32-3)18-22(20)23(29)7-5-4-6-16-33-26(30)28-14-12-19-8-10-21(27)11-9-19/h8-11,17-18,23H,4-7,12-16H2,1-3H3,(H,28,30)

Standard InChI Key:  LNUUQXSVSHKSOC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   17.0677   -9.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0665  -10.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813  -11.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7795   -9.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4949   -9.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4984  -10.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2175  -11.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9379  -10.7734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9345   -9.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2107   -9.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2198  -12.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5064  -12.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5087  -13.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7953  -13.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6535  -11.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3531   -9.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3529   -8.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3517  -11.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6376  -10.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7976  -14.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0842  -14.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3686  -14.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3664  -13.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6553  -14.9128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6575  -15.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9442  -16.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9464  -16.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2316  -17.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2335  -18.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9497  -18.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6654  -18.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6599  -17.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9530  -19.4472    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  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385324

   5-(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)pentyl N-[2-(4-chlorophenyl)ethyl]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: 475.03

Molecular Weight (Monoisotopic): 474.2285

AlogP: 5.42

#Rotatable Bonds: 11

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: ┄

CX Basic pKa: 8.31

CX LogP: 5.42

CX LogD: 4.46

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: 0.06

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