Phenyl N-[7-(indol-1-yl)heptyl]carbamate

ID: ALA3585525

PubChem CID: 122179641

Max Phase: Preclinical

Molecular Formula: C22H26N2O2

Molecular Weight: 350.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCCCn1ccc2ccccc21)Oc1ccccc1

Standard InChI:  InChI=1S/C22H26N2O2/c25-22(26-20-12-5-4-6-13-20)23-16-9-2-1-3-10-17-24-18-15-19-11-7-8-14-21(19)24/h4-8,11-15,18H,1-3,9-10,16-17H2,(H,23,25)

Standard InChI Key:  ULGSOYWNXCVYCD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    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 N   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
   11.3981    9.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1288   10.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   11.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3339   11.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7989   13.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7964   14.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289   13.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8638   12.4146    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 13  1  0
 13 20  1  0
 19 14  1  0
 14 12  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 25  1  0
 25 26  1  0
 26  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585525

   ---

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: 350.46

Molecular Weight (Monoisotopic): 350.1994

AlogP: 5.38

#Rotatable Bonds: 9

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: 5.51

CX LogD: 5.51

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -1.08

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