(S)-3-(4-(2,4-dihydroxybutan-2-yl)phenyl)-6-methylpyrrolo[1,2-a]pyrazin-1(2H)-one

ID: ALA5280682

Max Phase: Preclinical

Molecular Formula: C18H20N2O3

Molecular Weight: 312.37

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(=O)[nH]c(-c3ccc([C@@](C)(O)CCO)cc3)cn12

Standard InChI:  InChI=1S/C18H20N2O3/c1-12-3-8-16-17(22)19-15(11-20(12)16)13-4-6-14(7-5-13)18(2,23)9-10-21/h3-8,11,21,23H,9-10H2,1-2H3,(H,19,22)/t18-/m0/s1

Standard InChI Key:  SSRCPYMXFHISQW-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   -1.5068   -0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    0.0999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781   -0.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    0.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -1.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0623   -1.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068    2.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059    1.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059   -0.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4908    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2193   -0.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103   -2.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -2.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7763   -0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908    0.1008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

  1. Parent:

    ALA5280682

    ---

Associated Targets(Human)

TNKS Tchem Tankyrase-1 (1241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TNKS2 Tchem Tankyrase-2 (1531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PARP1 Tclin Poly [ADP-ribose] polymerase-1 (6206 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 312.37Molecular Weight (Monoisotopic): 312.1474AlogP: 2.19#Rotatable Bonds: 4
Polar Surface Area: 77.73Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 11.58CX Basic pKa: CX LogP: 0.90CX LogD: 0.90
Aromatic Rings: 3Heavy Atoms: 23QED Weighted: 0.69Np Likeness Score: -0.49

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