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

ID: ALA4550946

PubChem CID: 155555099

Max Phase: Preclinical

Molecular Formula: C20H24N2O3

Molecular Weight: 340.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C(C)(C)CCn1c2cc(OC)ccc2c2ccnc(C)c21

Standard InChI:  InChI=1S/C20H24N2O3/c1-13-18-16(8-10-21-13)15-7-6-14(24-4)12-17(15)22(18)11-9-20(2,3)19(23)25-5/h6-8,10,12H,9,11H2,1-5H3

Standard InChI Key:  FMWZAPSTHKUJSK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.7684  -15.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0627  -16.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7730  -16.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9068  -13.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9057  -13.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6137  -14.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6120  -12.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3206  -13.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3208  -13.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1038  -14.1364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1034  -12.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5844  -13.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4006  -13.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7368  -12.6374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2507  -11.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4363  -12.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8794  -14.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1977  -14.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4903  -13.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3574  -14.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8114  -15.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5190  -16.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7725  -17.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7194  -16.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2265  -18.2910    0.0000 C   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
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550946

   ---

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: 340.42

Molecular Weight (Monoisotopic): 340.1787

AlogP: 4.10

#Rotatable Bonds: 5

Polar Surface Area: 53.35

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.11

CX LogP: 3.32

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 0.14

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