methyl 2-(5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl)acetate

ID: ALA2323480

PubChem CID: 527316

Max Phase: Preclinical

Molecular Formula: C21H21NO5

Molecular Weight: 367.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1c(C)n(C(=O)c2ccc(OC)cc2)c2ccc(OC)cc12

Standard InChI:  InChI=1S/C21H21NO5/c1-13-17(12-20(23)27-4)18-11-16(26-3)9-10-19(18)22(13)21(24)14-5-7-15(25-2)8-6-14/h5-11H,12H2,1-4H3

Standard InChI Key:  RKLGIVJTQSFHOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.9359  -29.9363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6023  -29.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524  -28.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737  -29.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236  -28.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359  -30.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477  -27.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657  -29.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481  -31.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5737  -27.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738  -28.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154  -31.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9690  -27.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481  -32.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603  -30.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3853  -29.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1658  -28.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034  -29.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725  -32.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0063  -28.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725  -31.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603  -32.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7847  -32.4144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519  -27.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237  -27.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8306  -28.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838  -33.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  4  1  0
  6  1  1  0
  7  3  1  0
  8  4  2  0
  9  6  1  0
 10  7  1  0
 11  5  2  0
 12  6  2  0
 13 10  2  0
 14  9  2  0
 15  9  1  0
 16  2  1  0
 17 18  2  0
 18  8  1  0
 19 21  1  0
 20 10  1  0
 21 15  2  0
 22 14  1  0
 23 19  1  0
 24 17  1  0
 25 24  1  0
  3  5  1  0
 22 19  2  0
 11 17  1  0
 20 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2323480

   Methyl 2-[5-methoxy-1-(4-methoxybenzoyl)-2-methylindol-3-yl]acetate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.40

Molecular Weight (Monoisotopic): 367.1420

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.53

References

1. Liedtke AJ, Adeniji AO, Chen M, Byrns MC, Jin Y, Christianson DW, Marnett LJ, Penning TM..  (2013)  Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer.,  56  (6): [PMID:23432095] [10.1021/jm3017656]

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