(E)-(3-(3-Methylbut-2-en-1-yl)-4-((3-phenylpropanoyl)oxy)-styryl)boronic Acid

ID: ALA4439627

PubChem CID: 142412552

Max Phase: Preclinical

Molecular Formula: C22H25BO4

Molecular Weight: 364.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1cc(/C=C/B(O)O)ccc1OC(=O)CCc1ccccc1

Standard InChI:  InChI=1S/C22H25BO4/c1-17(2)8-11-20-16-19(14-15-23(25)26)9-12-21(20)27-22(24)13-10-18-6-4-3-5-7-18/h3-9,12,14-16,25-26H,10-11,13H2,1-2H3/b15-14+

Standard InChI Key:  BVLWTYPPSPGHHF-CCEZHUSRSA-N

Molfile:  

 
     RDKit          2D

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    7.1541  -22.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8621  -23.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5718  -22.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5689  -22.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8603  -21.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2751  -21.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9843  -22.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6905  -21.6150    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
    6.4460  -23.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7386  -22.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0306  -23.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7393  -22.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232  -22.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152  -23.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113  -22.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2037  -23.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026  -24.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150  -24.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196  -24.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474  -21.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472  -20.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394  -20.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392  -19.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318  -20.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3997  -22.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6874  -20.7979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
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  9 26  1  0
  9 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4439627

   ---

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: 364.25

Molecular Weight (Monoisotopic): 364.1846

AlogP: ┄

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HBA: ┄

HBD: ┄

#RO5 Violations: ┄

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HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

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CX LogD: ┄

Aromatic Rings: ┄

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QED Weighted: ┄

Np Likeness Score: ┄

References

1. Verma K, Zang T, Penning TM, Trippier PC..  (2019)  Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.,  62  (7): [PMID:30836001] [10.1021/acs.jmedchem.9b00090]

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