6-(7-Methoxy-1-methyl-beta-carbolin-9-yl)hexanamide

ID: ALA4483653

PubChem CID: 155540359

Max Phase: Preclinical

Molecular Formula: C19H23N3O2

Molecular Weight: 325.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c3ccnc(C)c3n(CCCCCC(N)=O)c2c1

Standard InChI:  InChI=1S/C19H23N3O2/c1-13-19-16(9-10-21-13)15-8-7-14(24-2)12-17(15)22(19)11-5-3-4-6-18(20)23/h7-10,12H,3-6,11H2,1-2H3,(H2,20,23)

Standard InChI Key:  KKYOYFUVFJOGLN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.4448  -11.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437  -12.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517  -12.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1499  -11.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586  -11.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8588  -12.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418  -12.6671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414  -11.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1224  -12.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9386  -11.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2748  -11.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7887  -10.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742  -10.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4173  -12.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356  -12.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283  -12.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8953  -13.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3493  -14.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6029  -14.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0569  -15.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3105  -16.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7645  -16.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181  -17.5986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9649  -16.6529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 10 14  1  0
  2 15  1  0
 15 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483653

   ---

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: 325.41

Molecular Weight (Monoisotopic): 325.1790

AlogP: 3.55

#Rotatable Bonds: 7

Polar Surface Area: 70.14

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 2.16

CX LogD: 2.14

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -0.20

References

1. Kumar K, Wang P, Wilson J, Zlatanic V, Berrouet C, Khamrui S, Secor C, Swartz EA, Lazarus M, Sanchez R, Stewart AF, Garcia-Ocana A, DeVita RJ..  (2020)  Synthesis and Biological Validation of a Harmine-Based, Central Nervous System (CNS)-Avoidant, Selective, Human β-Cell Regenerative Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase A (DYRK1A) Inhibitor.,  63  (6): [PMID:32003560] [10.1021/acs.jmedchem.9b01379]

Source

Source(1):

• Scientific Literature