require_relative "setup.rb"

class CompoundTest < MiniTest::Test

  def test_compound_from_smiles
    c = OpenTox::Compound.from_smiles "CC(=O)CC(C)C#N"
    assert_equal "InChI=1S/C6H9NO/c1-5(4-7)3-6(2)8/h5H,3H2,1-2H3", c.inchi
    assert_equal "CC(C#N)CC(=O)C", c.smiles
    c = OpenTox::Compound.from_smiles "N#[N+]C1=CC=CC=C1.F[B-](F)(F)F"
    assert_equal "InChI=1S/C6H5N2.BF4/c7-8-6-4-2-1-3-5-6;2-1(3,4)5/h1-5H;/q+1;-1", c.inchi
    assert_equal "F[B-](F)(F)F.N#[N+]c1ccccc1", c.smiles
  end

  def test_compound_from_name
    c = OpenTox::Compound.from_name "Benzene"
    assert_equal "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H", c.inchi
    assert_equal "c1ccccc1", c.smiles
    assert c.names.include? "benzene"
  end

  def test_compound_from_inchi
    c = OpenTox::Compound.from_inchi "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"
    assert_equal "c1ccccc1", c.smiles
  end

  def test_sdf_import
    c = OpenTox::Compound.from_sdf File.read(File.join DATA_DIR, "acetaldehyde.sdf")
    assert_equal "InChI=1S/C2H4O/c1-2-3/h2H,1H3", c.inchi
    assert_equal "CC=O", c.smiles
    assert c.names.include? "Acetylaldehyde"
  end

  def test_sdf_export
    c = OpenTox::Compound.from_smiles "CC=O"
    assert_match /7  6  0  0  0  0  0  0  0  0999 V2000/, c.sdf
  end

  def test_compound_image
    c = OpenTox::Compound.from_inchi "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"
    testbild = "/tmp/testbild.png"
    File.open(testbild, "w"){|f| f.puts c.png}
    assert_match "image/png", `file -b --mime-type /tmp/testbild.png`
    File.unlink(testbild)
  end

  def test_inchikey
    c = OpenTox::Compound.from_inchi "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"
    assert_equal "UHOVQNZJYSORNB-UHFFFAOYSA-N", c.inchikey
  end

  def test_cid
    c = OpenTox::Compound.from_inchi "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"
    assert_equal "241", c.cid
  end

  def test_chemblid
    skip "currently not needed, temporarily disabled"
    c = OpenTox::Compound.from_inchi "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"
    assert_equal "CHEMBL277500", c.chemblid
    c = OpenTox::Compound.from_smiles "OC[C@](c1onc(n1)c1ncn2c1CN(C)C(=O)c1c2cccc1Cl)(O)C"
    assert_equal "CHEMBL145418", c.chemblid
  end

  def test_sdf_storage
    c = OpenTox::Compound.from_smiles "CC(=O)CC(C)C#N"
    c.sdf
    assert !c.sdf_id.nil?
  end

  def test_fingerprint
    c = OpenTox::Compound.from_smiles "CC(=O)CC(C)C#N"

    assert_equal 9, c.fingerprint("FP4").size
  end

  def test_openbabel_segfault
    inchi = "InChI=1S/C19H27NO7/c1-11-9-19(12(2)27-19)17(23)26-14-6-8-20(4)7-5-13(15(14)21)10-25-16(22)18(11,3)24/h5,11-12,14,24H,6-10H2,1-4H3/t11-,12-,14-,18-,19?/m1/s1"

    c = Compound.from_inchi(inchi)
    assert_equal inchi, c.inchi
  end

  def test_openbabel_fingerprint
    [
      "CC(=O)CC(C)C#N",
      "CC(=O)CC(C)C",
      "C(=O)CC(C)C#N",
    ].each do |smi|
      c = OpenTox::Compound.from_smiles smi
      refute_nil c.fingerprint("FP4")
    end
  end

  def test_mna
    c = OpenTox::Compound.from_smiles "N#[N+]C1=CC=CC=C1.F[B-](F)(F)F"
    assert_equal 18, c.fingerprint("MNA").size
    assert_equal 9, c.fingerprint("MNA").uniq.size
  end

  def test_mpd
    c = OpenTox::Compound.from_smiles "N#[N+]C1=CC=CC=C1.F[B-](F)(F)F"
    assert 13, c.fingerprint("MP2D").size
    assert 7, c.fingerprint("MP2D").uniq.size
  end

  def test_molecular_weight
    c = OpenTox::Compound.from_smiles "CC(=O)CC(C)C"
    assert_equal 100.15888, c.molecular_weight.round(5)
  end

  def test_physchem
    c = OpenTox::Compound.from_smiles "CC(=O)CC(C)C"
    properties = c.calculate_properties(PhysChem.openbabel_descriptors)
    assert_equal PhysChem::OPENBABEL.size, properties.size
  end

  def test_openbabel_64bit_bug
    c = OpenTox::Compound.from_smiles "F[B-](F)(F)F.[Na+]"
    assert_equal "InChI=1S/BF4.Na/c2-1(3,4)5;/q-1;+1", c.inchi.chomp
    assert_equal "F[B-](F)(F)F.[Na+]", c.smiles, "A failure here might be caused by a compound webservice running on 64bit architectures using an outdated version of OpenBabel. Please install OpenBabel version 2.3.2 or higher." # seems to be fixed in 2.3.2
  end
end