6-(hydroxymethyl)-3-(4-(2-hydroxypropan-2-yl)phenyl)pyrrolo[1,2-a]pyrazin-1(2H)-one

ID: ALA5281885

Max Phase: Preclinical

Molecular Formula: C17H18N2O3

Molecular Weight: 298.34

Names and Identifiers

Canonical SMILES:  CC(C)(O)c1ccc(-c2cn3c(CO)ccc3c(=O)[nH]2)cc1

Standard InChI:  InChI=1S/C17H18N2O3/c1-17(2,22)12-5-3-11(4-6-12)14-9-19-13(10-20)7-8-15(19)16(21)18-14/h3-9,20,22H,10H2,1-2H3,(H,18,21)

Standard InChI Key:  XPFCXDCYIAOOBE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.8642    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4353    0.9757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4353    0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -0.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.1506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790   -0.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934    0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -1.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790   -1.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195   -1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1337   -1.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497    2.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488    1.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1337    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8624   -0.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  1  6  1  0
  6  5  1  0
  7  4  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
  7 12  1  0
 12 11  2  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  2 17  2  0
  1 18  2  0
  6 19  1  0
 19 20  2  0
 20 18  1  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281885

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 298.34

Molecular Weight (Monoisotopic): 298.1317

AlogP: 2.01

#Rotatable Bonds: 3

Polar Surface Area: 77.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.50

CX Basic pKa: ┄

CX LogP: 0.84

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -0.22

References

1. Buchstaller HP, Anlauf U, Dorsch D, Kögler S, Kuhn D, Lehmann M, Leuthner B, Lodholz S, Musil D, Radtki D, Rettig C, Ritzert C, Rohdich F, Schneider R, Wegener A, Weigt S, Wilkinson K, Esdar C..  (2021)  Optimization of a Screening Hit toward M2912, an Oral Tankyrase Inhibitor with Antitumor Activity in Colorectal Cancer Models.,  64  (14.0): [PMID:34255518] [10.1021/acs.jmedchem.1c00800]

Source

Source(1):

• Scientific Literature