2-(7-Methoxy-1-methyl-beta-carbolin-9-yl)acetic Acid Methyl Ester

ID: ALA4521356

PubChem CID: 155542559

Max Phase: Preclinical

Molecular Formula: C16H16N2O3

Molecular Weight: 284.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)Cn1c2cc(OC)ccc2c2ccnc(C)c21

Standard InChI:  InChI=1S/C16H16N2O3/c1-10-16-13(6-7-17-10)12-5-4-11(20-2)8-14(12)18(16)9-15(19)21-3/h4-8H,9H2,1-3H3

Standard InChI Key:  RDBHSCKYWGGFIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    3.0321   -3.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0310   -4.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -3.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -3.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -4.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291   -4.4869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2286   -3.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7097   -3.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -3.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8621   -2.9879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3760   -2.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615   -2.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0046   -4.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229   -4.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -4.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826   -5.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9366   -5.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902   -6.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1371   -5.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6442   -7.2567    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
 18 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521356

   ---

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: 284.31

Molecular Weight (Monoisotopic): 284.1161

AlogP: 2.68

#Rotatable Bonds: 3

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: 6.08

CX LogP: 1.69

CX LogD: 1.67

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.38

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