Phenyl N-(4-indol-1-ylbutyl)carbamate

ID: ALA3585523

PubChem CID: 101885730

Max Phase: Preclinical

Molecular Formula: C19H20N2O2

Molecular Weight: 308.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCn1ccc2ccccc21)Oc1ccccc1

Standard InChI:  InChI=1S/C19H20N2O2/c22-19(23-17-9-2-1-3-10-17)20-13-6-7-14-21-15-12-16-8-4-5-11-18(16)21/h1-5,8-12,15H,6-7,13-14H2,(H,20,22)

Standard InChI Key:  XKHOBBDASOWMSC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    6.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241    6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    7.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3245    5.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4611    8.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9311    9.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3997    9.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3984    8.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9284    7.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4598    7.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 14 15  1  0
 15 19  1  0
 18 16  1  0
 16 14  2  0
 15 17  1  0
 17  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA3585523

   phenyl N-(4-indol-1-ylbutyl)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: 308.38

Molecular Weight (Monoisotopic): 308.1525

AlogP: 4.21

#Rotatable Bonds: 6

Polar Surface Area: 43.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -1.26

References

1. Terwege T, Dahlhaus H, Hanekamp W, Lehr M.  (2014)  -Heteroarylalkylcarbamates as inhibitors of fatty acid amide hydrolase (FAAH),  5  (7): [10.1039/C4MD00181H]

2. Dahlhaus H, Hanekamp W, Lehr M..  (2017)  (Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH).,  8  (3): [PMID:30108777] [10.1039/C6MD00683C]

Source

Source(1):

• Scientific Literature