(S)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid

ID: ALA4466610

PubChem CID: 66706325

Max Phase: Preclinical

Molecular Formula: C15H16O3

Molecular Weight: 244.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H](C(=O)O)c1ccc2cc(OC)ccc2c1

Standard InChI:  InChI=1S/C15H16O3/c1-3-14(15(16)17)12-5-4-11-9-13(18-2)7-6-10(11)8-12/h4-9,14H,3H2,1-2H3,(H,16,17)/t14-/m0/s1

Standard InChI Key:  LSDAHSHHKKHOKE-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   10.5714   -7.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5692   -8.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2772   -8.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775   -6.8352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8635   -6.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1552   -8.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8632   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8609   -9.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1507   -9.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4428   -9.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7367   -9.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0287   -9.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0309   -8.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7370   -8.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -8.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9839   -8.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3243   -9.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3224  -10.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  6 15  2  0
 10 15  1  0
  2  7  1  0
  3 16  1  0
 17 18  1  0
 12 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4466610

   (2S)-2-(6-methoxynaphthalen-2-yl)butanoic acid

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: 244.29

Molecular Weight (Monoisotopic): 244.1099

AlogP: 3.43

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.26

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.90

Np Likeness Score: -0.05

References

1. Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM..  (2016)  Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor.,  59  (16): [PMID:27486833] [10.1021/acs.jmedchem.6b00160]

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