(S)-N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

ID: ALA4476642

PubChem CID: 155538637

Max Phase: Preclinical

Molecular Formula: C19H28N4O2

Molecular Weight: 344.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCn1cc(C(=O)N[C@H](C(N)=O)C(C)(C)C)c2cccnc21

Standard InChI:  InChI=1S/C19H28N4O2/c1-5-6-7-11-23-12-14(13-9-8-10-21-17(13)23)18(25)22-15(16(20)24)19(2,3)4/h8-10,12,15H,5-7,11H2,1-4H3,(H2,20,24)(H,22,25)/t15-/m1/s1

Standard InChI Key:  QDZHLYBDQFZWCJ-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.3712  -22.4934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6568  -22.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517  -21.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9476  -22.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650  -23.4956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8673  -23.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946  -22.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384  -21.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359  -21.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900  -21.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7374  -24.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9211  -24.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894  -25.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731  -25.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455  -25.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0771  -22.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7866  -22.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7903  -23.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0735  -21.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7794  -20.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3640  -20.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4925  -22.0754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0687  -20.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497  -22.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506  -22.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  7  1  0
 25  5  1  0
  5  6  1  0
  6  4  2  0
 25  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
 16 17  1  0
 17 18  2  0
 16 19  1  1
 19 20  1  0
 19 21  1  0
 17 22  1  0
 19 23  1  0
 10 24  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476642

   ---

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: 344.46

Molecular Weight (Monoisotopic): 344.2212

AlogP: 2.86

#Rotatable Bonds: 7

Polar Surface Area: 90.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.12

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.81

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]

2. Sparkes E, Cairns EA, Kevin RC, Lai F, Grafinger KE, Chen S, Deventer MH, Ellison R, Boyd R, Martin LJ, McGregor IS, Gerona RR, Hibbs DE, Auwärter V, Glass M, Stove C, Banister SD..  (2022)  Structure-activity relationships of valine, tert-leucine, and phenylalanine amino acid-derived synthetic cannabinoid receptor agonists related to ADB-BUTINACA, APP-BUTINACA, and ADB-P7AICA.,  13  (2.0): [PMID:35308023] [10.1039/d1md00242b]

Source

Source(1):

• Scientific Literature