N-(4-chlorobenzoyl)-melatonin

ID: ALA4742775

PubChem CID: 86086004

Max Phase: Preclinical

Molecular Formula: C20H19ClN2O3

Molecular Weight: 370.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(CCNC(C)=O)cn2C(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H19ClN2O3/c1-13(24)22-10-9-15-12-23(19-8-7-17(26-2)11-18(15)19)20(25)14-3-5-16(21)6-4-14/h3-8,11-12H,9-10H2,1-2H3,(H,22,24)

Standard InChI Key:  NDAAJXSISJLIBF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.9271   -8.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9259   -8.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6408   -9.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6389   -7.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3543   -8.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3591   -8.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1465   -9.2272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6284   -8.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1387   -7.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2126   -7.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2124   -6.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3890   -7.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1950   -6.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4452   -6.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4061  -10.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8576  -10.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2140  -10.1771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0513  -10.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5032  -11.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7625  -11.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5751  -12.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1198  -11.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2149  -12.4737    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.2511   -5.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5015   -5.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8067   -6.5753    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  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 20 23  1  0
 14 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4742775

   n-(4-Chlorobenzoyl)-melatonin

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: 370.84

Molecular Weight (Monoisotopic): 370.1084

AlogP: 3.67

#Rotatable Bonds: 5

Polar Surface Area: 60.33

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -1.07

References

1. Liu Y,He S,Chen Y,Liu Y,Feng F,Liu W,Guo Q,Zhao L,Sun H.  (2020)  Overview of AKR1C3: Inhibitor Achievements and Disease Insights.,  63  (20.0): [PMID:32463235] [10.1021/acs.jmedchem.9b02138]

2. Adeniji, Adegoke O AO and 5 more authors.  2011-03-01  Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3).  [PMID:21277203]

3. Adeniji, Adegoke O AO and 6 more authors.  2012-03-08  Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N-phenyl-aminobenzoates and their structure-activity relationships.  [PMID:22263837]

4. Brožič, Petra and 7 more authors.  2012-09-13  Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library.  [PMID:22881866]

5. Hendriks, Christine M M and 7 more authors.  2015-10-15  Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities.  [PMID:26372652]

6. Pippione, Agnese C AC and 12 more authors.  2017-10-20  Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach.  [PMID:28881288]

7. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

8. Pippione, Agnese Chiara AC and 15 more authors.  2018-04-25  Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid.  [PMID:29602039]

Source

Source(1):

• Scientific Literature