(S)-N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-hydroxypentyl)-1H-indole-2-carboxamide

ID: ALA4514713

PubChem CID: 155539564

Max Phase: Preclinical

Molecular Formula: C20H29N3O3

Molecular Weight: 359.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)[C@H](NC(=O)c1cc2ccccc2n1CCCCCO)C(N)=O

Standard InChI:  InChI=1S/C20H29N3O3/c1-20(2,3)17(18(21)25)22-19(26)16-13-14-9-5-6-10-15(14)23(16)11-7-4-8-12-24/h5-6,9-10,13,17,24H,4,7-8,11-12H2,1-3H3,(H2,21,25)(H,22,26)/t17-/m1/s1

Standard InChI Key:  IEZMJVDWIFQOBY-QGZVFWFLSA-N

Molfile:  

 
     RDKit          2D

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   29.4561  -21.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9766  -21.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9852  -22.4903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2022  -22.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1983  -21.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4837  -21.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7724  -21.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7803  -22.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4955  -22.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2448  -23.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6994  -23.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9631  -24.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4177  -25.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2774  -21.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6947  -22.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6855  -21.1064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5160  -22.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6773  -26.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9292  -23.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9200  -21.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7413  -21.8008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5068  -21.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5252  -23.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7505  -23.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1361  -26.6723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3368  -23.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  5  1  0
  4  3  1  0
  3  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 13 18  1  0
 17 19  1  6
 17 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  0
 19 24  1  0
 18 25  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514713

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.47

Molecular Weight (Monoisotopic): 359.2209

AlogP: 2.43

#Rotatable Bonds: 8

Polar Surface Area: 97.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.50

References

1. Moir M, Lane S, Lai F, Connor M, Hibbs DE, Kassiou M..  (2019)  Strategies to develop selective CB₂ receptor agonists from indole carboxamide synthetic cannabinoids.,  180  [PMID:31319265] [10.1016/j.ejmech.2019.07.036]

Source

Source(1):

• Scientific Literature