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

ID: ALA4442374

PubChem CID: 155515881

Max Phase: Preclinical

Molecular Formula: C19H22N2O3

Molecular Weight: 326.40

Molecule Type: Unknown

Names and Identifiers

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

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

Standard InChI Key:  UKIATPGUBXMJLS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.4613  -13.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602  -14.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682  -14.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664  -12.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751  -13.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753  -14.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583  -14.4707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579  -13.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1389  -13.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9551  -13.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2913  -12.9717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052  -12.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9907  -12.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338  -14.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522  -14.6245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448  -14.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9119  -15.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659  -15.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6194  -16.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0734  -17.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270  -18.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739  -17.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810  -18.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4190  -16.8013    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
 21 23  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4442374

   ---

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: 3.71

#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: 2.76

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.02

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