Phenyl N-[5-(indol-1-yl)pentyl]carbamate

ID: ALA3585524

PubChem CID: 101885731

Max Phase: Preclinical

Molecular Formula: C20H22N2O2

Molecular Weight: 322.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCn1ccc2ccccc21)Oc1ccccc1

Standard InChI:  InChI=1S/C20H22N2O2/c23-20(24-18-10-3-1-4-11-18)21-14-7-2-8-15-22-16-13-17-9-5-6-12-19(17)22/h1,3-6,9-13,16H,2,7-8,14-15H2,(H,21,23)

Standard InChI Key:  AJEKGGDZKJRXMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241    6.4042    0.0000 N   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
    9.4611    8.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1918    8.7241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9293    9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3969    9.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8619   11.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8594   12.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3919   12.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9268   10.6803    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
    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
    4.1182    4.3614    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
  4  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 14 15  1  0
 15 19  1  0
 18 16  1  0
 16 14  2  0
 15 17  1  0
 17 13  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
 13 24  1  0
 24  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585524

   phenyl N-(5-indol-1-ylpentyl)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: 322.41

Molecular Weight (Monoisotopic): 322.1681

AlogP: 4.60

#Rotatable Bonds: 7

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: 4.62

CX LogD: 4.62

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -1.17

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