Phenyl N-[8-(indol-1-yl)octyl]carbamate

ID: ALA3585526

PubChem CID: 101885732

Max Phase: Preclinical

Molecular Formula: C23H28N2O2

Molecular Weight: 364.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCCCCn1ccc2ccccc21)Oc1ccccc1

Standard InChI:  InChI=1S/C23H28N2O2/c26-23(27-21-13-6-5-7-14-21)24-17-10-3-1-2-4-11-18-25-19-16-20-12-8-9-15-22(20)25/h5-9,12-16,19H,1-4,10-11,17-18H2,(H,24,26)

Standard InChI Key:  HUCXRDNIIGIBSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.4611    8.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9293    9.5644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3981    9.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   11.2987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1985    8.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3351   11.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8052   13.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2738   13.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2724   12.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8025   10.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3339   10.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    7.8301    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
    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
    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
    6.0553    6.0958    0.0000 C   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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12  1  1  0
 13 14  1  0
 14 21  1  0
 20 15  1  0
 15 13  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
 19 26  1  0
 26 27  1  0
 27 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585526

   phenyl N-(8-indol-1-yloctyl)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: 364.49

Molecular Weight (Monoisotopic): 364.2151

AlogP: 5.77

#Rotatable Bonds: 10

Polar Surface Area: 43.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.95

CX LogD: 5.95

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -1.04

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