3-(7-Methoxy-1-methyl-beta-carbolin-9-yl)propionic Acid Hydrochloride

ID: ALA4528315

PubChem CID: 155545528

Max Phase: Preclinical

Molecular Formula: C16H17ClN2O3

Molecular Weight: 284.31

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16N2O3.ClH/c1-10-16-13(5-7-17-10)12-4-3-11(21-2)9-14(12)18(16)8-6-15(19)20;/h3-5,7,9H,6,8H2,1-2H3,(H,19,20);1H

Standard InChI Key:  ALSUAPUBPGXZCM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   30.3310  -17.0826    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.2436  -14.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2425  -15.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9505  -15.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9487  -14.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6574  -14.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6576  -15.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4406  -15.5438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4402  -14.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9212  -14.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7374  -14.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0736  -14.0448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5875  -13.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7730  -13.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2161  -15.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5345  -15.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8271  -15.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6942  -16.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1482  -16.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4017  -17.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8557  -18.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2013  -17.8743    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
 20 21  1  0
 20 22  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: 284.31

Molecular Weight (Monoisotopic): 284.1161

AlogP: 2.98

#Rotatable Bonds: 4

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: 4.40

CX Basic pKa: 6.11

CX LogP: 0.35

CX LogD: -0.86

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -0.10

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