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

ID: ALA4553904

PubChem CID: 155555587

Max Phase: Preclinical

Molecular Formula: C15H15ClN2O3

Molecular Weight: 270.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c3ccnc(C)c3n(CC(=O)O)c2c1.Cl

Standard InChI:  InChI=1S/C15H14N2O3.ClH/c1-9-15-12(5-6-16-9)11-4-3-10(20-2)7-13(11)17(15)8-14(18)19;/h3-7H,8H2,1-2H3,(H,18,19);1H

Standard InChI Key:  JWTGJAJWCCWPSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   22.1054  -17.1115    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.2657  -14.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2646  -15.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9726  -15.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9708  -13.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6794  -14.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6797  -15.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4627  -15.3746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4622  -14.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9433  -14.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7595  -14.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0957  -13.8756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6096  -13.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7951  -13.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2382  -15.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5565  -15.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8491  -15.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7162  -16.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1702  -16.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4238  -17.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3707  -16.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 11 15  1  0
  3 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

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: 270.29

Molecular Weight (Monoisotopic): 270.1004

AlogP: 2.59

#Rotatable Bonds: 3

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: 4.06

CX Basic pKa: 6.11

CX LogP: 0.01

CX LogD: -1.20

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: -0.16

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