3-oxo-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline-7,8-dicarboxylic acid

ID: ALA4435241

PubChem CID: 155511105

Max Phase: Preclinical

Molecular Formula: C14H13NO5

Molecular Weight: 275.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(cc1C(=O)O)CN1C(=O)CCC1C2

Standard InChI:  InChI=1S/C14H13NO5/c16-12-2-1-9-3-7-4-10(13(17)18)11(14(19)20)5-8(7)6-15(9)12/h4-5,9H,1-3,6H2,(H,17,18)(H,19,20)

Standard InChI Key:  UNJZWCJMAZECLF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    6.4545  -11.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641  -12.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7499  -12.3321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451  -11.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580  -11.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747  -11.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9657  -12.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1639  -11.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1623  -12.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8707  -12.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5770  -12.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5746  -11.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8698  -11.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7178  -13.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2892  -12.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2900  -13.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0006  -12.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2851  -11.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9983  -11.5035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2825  -10.2759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  2  9  1  0
  8  1  1  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  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
  7 14  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4435241

   ---

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: 275.26

Molecular Weight (Monoisotopic): 275.0794

AlogP: 1.13

#Rotatable Bonds: 2

Polar Surface Area: 94.91

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.89

CX Basic pKa: ┄

CX LogP: 0.78

CX LogD: -4.66

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.84

Np Likeness Score: 0.05

References

1. Santos ARN, Sheldrake HM, Ibrahim AIM, Danta CC, Bonanni D, Daga M, Oliaro-Bosso S, Boschi D, Lolli ML, Pors K..  (2019)  Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo-keto reductase 1C3 target affinity.,  10  (8): [PMID:31673310] [10.1039/C9MD00201D]

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