N-Acetyl-4-(7-methoxy-1-methyl-beta-carbolin-9-yl)butylamine

ID: ALA4476003

PubChem CID: 155538036

Max Phase: Preclinical

Molecular Formula: C19H23N3O2

Molecular Weight: 325.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c3ccnc(C)c3n(CCCCNC(C)=O)c2c1

Standard InChI:  InChI=1S/C19H23N3O2/c1-13-19-17(8-10-20-13)16-7-6-15(24-3)12-18(16)22(19)11-5-4-9-21-14(2)23/h6-8,10,12H,4-5,9,11H2,1-3H3,(H,21,23)

Standard InChI Key:  YMYZMIQUFMWKQL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   21.2538  -22.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2527  -23.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9607  -24.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9589  -22.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6675  -22.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6678  -23.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4508  -24.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4504  -22.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9314  -23.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7476  -23.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0838  -22.5097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5977  -21.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7832  -21.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2263  -23.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5446  -24.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8372  -23.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7043  -24.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1583  -25.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4119  -26.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8659  -26.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1195  -27.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5735  -28.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8271  -28.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7739  -27.9945    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:

   

   ALA4476003

   ---

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: 3.42

#Rotatable Bonds: 6

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 1.67

CX LogD: 1.65

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: -0.42

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