6-(7-Methoxy-1-methyl-beta-carbolin-9-yl)hexanoic Acid Methyl Ester

ID: ALA4513287

PubChem CID: 155538975

Max Phase: Preclinical

Molecular Formula: C20H24N2O3

Molecular Weight: 340.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)CCCCCn1c2cc(OC)ccc2c2ccnc(C)c21

Standard InChI:  InChI=1S/C20H24N2O3/c1-14-20-17(10-11-21-14)16-9-8-15(24-2)13-18(16)22(20)12-6-4-5-7-19(23)25-3/h8-11,13H,4-7,12H2,1-3H3

Standard InChI Key:  AZCAKTVAQNDAPW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   34.4774   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4763   -3.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1843   -4.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1826   -2.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8912   -3.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8914   -3.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6744   -4.1980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6740   -2.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1550   -3.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9712   -3.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3074   -2.6990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8213   -2.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0069   -2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4500   -4.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7683   -4.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0609   -3.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9280   -4.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3820   -5.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6356   -6.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0896   -6.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3431   -7.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7971   -8.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0507   -9.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5047   -9.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9976   -8.1838    0.0000 O   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
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513287

   ---

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: 340.42

Molecular Weight (Monoisotopic): 340.1787

AlogP: 4.24

#Rotatable Bonds: 7

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: 6.04

CX LogP: 3.11

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: -0.05

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