5-(7-Methoxy-1-methyl-beta-carbolin-9-yl)pentanamide

ID: ALA4563765

PubChem CID: 155559198

Max Phase: Preclinical

Molecular Formula: C18H21N3O2

Molecular Weight: 311.39

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O2/c1-12-18-15(8-9-20-12)14-7-6-13(23-2)11-16(14)21(18)10-4-3-5-17(19)22/h6-9,11H,3-5,10H2,1-2H3,(H2,19,22)

Standard InChI Key:  OMMAZMKIESJSJP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   30.3915   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3904   -3.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0984   -4.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0966   -2.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8052   -3.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8055   -3.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5885   -4.1237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5880   -2.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0691   -3.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8853   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2215   -2.6247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7354   -1.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9209   -2.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3640   -4.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6823   -4.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9749   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8420   -4.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2960   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5496   -6.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0036   -6.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2572   -7.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7112   -8.2784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0567   -7.8392    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
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4563765

   ---

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: 3.16

#Rotatable Bonds: 6

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: 1.71

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: -0.26

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