4-(7-Methoxy-1-methyl-beta-carbolin-9-yl)butyric Acid Hydrochloride

ID: ALA4539999

PubChem CID: 155550070

Max Phase: Preclinical

Molecular Formula: C17H19ClN2O3

Molecular Weight: 298.34

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N2O3.ClH/c1-11-17-14(7-8-18-11)13-6-5-12(22-2)10-15(13)19(17)9-3-4-16(20)21;/h5-8,10H,3-4,9H2,1-2H3,(H,20,21);1H

Standard InChI Key:  UIEXRNRVTDHPCG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   37.4711  -17.3921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.9698  -14.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9687  -15.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6767  -15.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6749  -14.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3835  -14.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3838  -15.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1668  -15.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1663  -14.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6474  -15.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4636  -14.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7998  -14.1810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3137  -13.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4992  -13.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9423  -15.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2606  -15.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5532  -15.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4203  -16.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8743  -17.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1279  -17.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5819  -18.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8355  -19.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7823  -18.2809    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
 21 22  1  0
 21 23  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: 298.34

Molecular Weight (Monoisotopic): 298.1317

AlogP: 3.37

#Rotatable Bonds: 5

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: 4.32

CX Basic pKa: 6.11

CX LogP: 0.61

CX LogD: -0.61

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -0.04

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