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

ID: ALA4514653

PubChem CID: 155539435

Max Phase: Preclinical

Molecular Formula: C17H18N2O3

Molecular Weight: 298.34

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N2O3/c1-11-17-14(6-8-18-11)13-5-4-12(21-2)10-15(13)19(17)9-7-16(20)22-3/h4-6,8,10H,7,9H2,1-3H3

Standard InChI Key:  QLMKOBFAGMGYOS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.5395   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5384   -4.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2464   -4.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2446   -2.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9533   -3.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9535   -4.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7365   -4.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7361   -3.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2171   -3.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0333   -3.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3695   -2.9095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8834   -2.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0689   -2.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5120   -4.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8303   -4.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1230   -4.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9900   -5.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4441   -5.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976   -6.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1516   -7.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4972   -6.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3521   -7.0094    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
 19 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514653

   ---

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: 3.07

#Rotatable Bonds: 4

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: 6.10

CX LogP: 1.93

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -0.21

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]

2. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(1):

• Scientific Literature