Phenyl N-(6-indol-1-ylhexyl)carbamate

ID: ALA3585519

PubChem CID: 101885724

Max Phase: Preclinical

Molecular Formula: C21H24N2O2

Molecular Weight: 336.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCCn1ccc2ccccc21)Oc1ccccc1

Standard InChI:  InChI=1S/C21H24N2O2/c24-21(25-19-11-4-3-5-12-19)22-15-8-1-2-9-16-23-17-14-18-10-6-7-13-20(18)23/h3-7,10-14,17H,1-2,8-9,15-16H2,(H,22,24)

Standard InChI Key:  VCBRDEPSMWRLKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    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
    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
    7.9923    7.8301    0.0000 N   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
    9.9293    9.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2615    7.2445    0.0000 O   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
   11.8681   11.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3368   11.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3354   10.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8655    9.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3968    8.7536    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 21  1  0
 20  3  1  0
  3  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  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
M  END

Alternative Forms

1. Parent:

   

   ALA3585519

   phenyl N-(6-indol-1-ylhexyl)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: 336.44

Molecular Weight (Monoisotopic): 336.1838

AlogP: 4.99

#Rotatable Bonds: 8

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: 5.06

CX LogD: 5.06

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -1.12

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