2-Methyl-4-(7-methoxy-1-methyl-beta-carbolin-9-yl)butanamide

ID: ALA4575812

PubChem CID: 139520310

Max Phase: Preclinical

Molecular Formula: C18H21N3O2

Molecular Weight: 311.39

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O2/c1-11(18(19)22)7-9-21-16-10-13(23-3)4-5-14(16)15-6-8-20-12(2)17(15)21/h4-6,8,10-11H,7,9H2,1-3H3,(H2,19,22)

Standard InChI Key:  KARNDMDMYXIFGI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.4476  -11.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4465  -12.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1612  -12.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1595  -11.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8748  -11.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8750  -12.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6654  -12.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6650  -11.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1506  -11.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9745  -11.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3139  -11.0907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8232  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0011  -10.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4579  -12.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7318  -12.7591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0177  -12.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9214  -13.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3703  -14.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6262  -14.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0750  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3310  -16.1841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2679  -15.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4333  -14.9566    0.0000 C   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
 20 22  2  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4575812

   ---

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: 311.39

Molecular Weight (Monoisotopic): 311.1634

AlogP: 3.02

#Rotatable Bonds: 5

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: 6.11

CX LogP: 1.81

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.08

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