7,8-bis(hydroxymethyl)-1,2,10,10a-tetrahydropyrrolo[1,2-b]isoquinolin-3(5H)-one

ID: ALA4444059

PubChem CID: 155516999

Max Phase: Preclinical

Molecular Formula: C14H17NO3

Molecular Weight: 247.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCC2Cc3cc(CO)c(CO)cc3CN12

Standard InChI:  InChI=1S/C14H17NO3/c16-7-11-3-9-5-13-1-2-14(18)15(13)6-10(9)4-12(11)8-17/h3-4,13,16-17H,1-2,5-8H2

Standard InChI Key:  AKEFIEHUIVCTTD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   30.9950   -1.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0046   -3.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2904   -3.2275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2856   -2.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4985   -2.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0152   -2.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5062   -3.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7044   -2.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7028   -3.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4112   -3.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1175   -3.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1151   -2.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4103   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2583   -4.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8297   -3.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8305   -4.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8256   -1.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5388   -2.3989    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  1  0
 12 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4444059

   ---

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: 247.29

Molecular Weight (Monoisotopic): 247.1208

AlogP: 0.72

#Rotatable Bonds: 2

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.07

CX LogD: -0.07

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.81

Np Likeness Score: 0.45

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