2,2-Dimethyl-4-(7-methoxy-1-methyl-beta-carbolin-9-yl)butyric Acid

ID: ALA4521234

PubChem CID: 155542573

Max Phase: Preclinical

Molecular Formula: C19H22N2O3

Molecular Weight: 326.40

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H22N2O3/c1-12-17-15(7-9-20-12)14-6-5-13(24-4)11-16(14)21(17)10-8-19(2,3)18(22)23/h5-7,9,11H,8,10H2,1-4H3,(H,22,23)

Standard InChI Key:  XRZSKNMILHLGAE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   29.4395  -27.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7338  -28.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4441  -28.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5779  -25.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5768  -25.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2848  -26.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2830  -24.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9917  -25.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9919  -25.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7749  -26.1590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7745  -24.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2555  -25.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0717  -25.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4079  -24.6600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9218  -23.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1073  -24.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5505  -26.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8688  -26.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1614  -25.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0285  -26.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4825  -27.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1900  -28.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4436  -29.7056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3905  -28.7599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
  5 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521234

   ---

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: 326.40

Molecular Weight (Monoisotopic): 326.1630

AlogP: 4.01

#Rotatable Bonds: 5

Polar Surface Area: 64.35

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.34

CX Basic pKa: 6.11

CX LogP: 1.72

CX LogD: 0.50

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: 0.23

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