biotite 1.5.0__cp313-cp313-manylinux_2_24_x86_64.manylinux_2_28_x86_64.whl

biotite/structure/io/mol/ctab.py

@@ -0,0 +1,420 @@
+# This source code is part of the Biotite package and is distributed
+# under the 3-Clause BSD License. Please see 'LICENSE.rst' for further
+# information.
+
+"""
+Functions for parsing and writing an :class:`AtomArray` from/to
+*MDL* connection tables (Ctab).
+"""
+
+__name__ = "biotite.structure.io.mol"
+__author__ = "Patrick Kunzmann"
+__all__ = ["read_structure_from_ctab", "write_structure_to_ctab"]
+
+import itertools
+import shlex
+import warnings
+import numpy as np
+from biotite.file import InvalidFileError
+from biotite.structure.atoms import AtomArray, AtomArrayStack
+from biotite.structure.bonds import BondList, BondType
+from biotite.structure.error import BadStructureError
+from biotite.structure.io.util import number_of_integer_digits
+
+BOND_TYPE_MAPPING = {
+    1: BondType.SINGLE,
+    2: BondType.DOUBLE,
+    3: BondType.TRIPLE,
+    4: BondType.AROMATIC,
+    5: BondType.ANY,
+    6: BondType.AROMATIC_SINGLE,
+    7: BondType.AROMATIC_DOUBLE,
+    8: BondType.ANY,
+}
+BOND_TYPE_MAPPING_REV = {v: k for k, v in BOND_TYPE_MAPPING.items()}
+
+CHARGE_MAPPING = {0: 0, 1: 3, 2: 2, 3: 1, 5: -1, 6: -2, 7: -3}
+CHARGE_MAPPING_REV = {val: key for key, val in CHARGE_MAPPING.items()}
+
+V2000_COMPATIBILITY_LINE = "  0  0  0  0  0  0  0  0  0  0999 V3000"
+# The number of charges per `M  CHG` line
+N_CHARGES_PER_LINE = 8
+
+
+def read_structure_from_ctab(ctab_lines):
+    """
+    Parse a *MDL* connection table (Ctab) to obtain an
+    :class:`AtomArray`.
+    :footcite:`Dalby1992`
+
+    Parameters
+    ----------
+    ctab_lines : lines of str
+        The lines containing the *ctab*.
+        Must begin with the *counts* line and end with the `M END` line.
+
+    Returns
+    -------
+    atoms : AtomArray
+        This :class:`AtomArray` contains the optional ``charge``
+        annotation and has an associated :class:`BondList`.
+
+    References
+    ----------
+
+    ``V3000`` specification was taken from
+    `<https://discover.3ds.com/sites/default/files/2020-08/biovia_ctfileformats_2020.pdf>`_.
+
+    .. footbibliography::
+    """
+    match _get_version(ctab_lines[0]):
+        case "V2000":
+            return _read_structure_from_ctab_v2000(ctab_lines)
+        case "V3000":
+            return _read_structure_from_ctab_v3000(ctab_lines)
+        case "":
+            raise InvalidFileError("CTAB counts line misses version")
+        case unkown_version:
+            raise InvalidFileError(f"Unknown CTAB version '{unkown_version}'")
+
+
+def write_structure_to_ctab(atoms, default_bond_type=BondType.ANY, version=None):
+    """
+    Convert an :class:`AtomArray` into a
+    *MDL* connection table (Ctab).
+    :footcite:`Dalby1992`
+
+    Parameters
+    ----------
+    atoms : AtomArray
+        The array must have an associated :class:`BondList`.
+    default_bond_type : BondType, optional
+        Bond type fallback for the *Bond block*, if a :class:`BondType`
+        has no CTAB counterpart.
+        By default, each such bond is treated as :attr:`BondType.ANY`.
+    version : {"V2000", "V3000"}, optional
+        The version of the CTAB format.
+        ``"V2000"`` uses the *Atom* and *Bond* block, while ``"V3000"``
+        uses the *Properties* block.
+        By default, ``"V2000"`` is used, unless the number of atoms or
+        bonds exceeds 999, in which case ``"V3000"`` is used.
+
+    Returns
+    -------
+    ctab_lines : lines of str
+        The lines containing the *ctab*.
+        The lines begin with the *counts* line and end with the `M END`
+        line.
+
+    References
+    ----------
+
+    ``V3000`` specification was taken from
+    `<https://discover.3ds.com/sites/default/files/2020-08/biovia_ctfileformats_2020.pdf>`_.
+
+    .. footbibliography::
+    """
+    if isinstance(atoms, AtomArrayStack):
+        raise TypeError(
+            "An 'AtomArrayStack' was given, but only a single model can be written"
+        )
+    if atoms.bonds is None:
+        raise BadStructureError("Input AtomArray has no associated BondList")
+    if np.isnan(atoms.coord).any():
+        raise BadStructureError("Input AtomArray has NaN coordinates")
+
+    match version:
+        case None:
+            if _is_v2000_compatible(atoms.array_length(), atoms.bonds.get_bond_count()):
+                return _write_structure_to_ctab_v2000(atoms, default_bond_type)
+            else:
+                return _write_structure_to_ctab_v3000(atoms, default_bond_type)
+        case "V2000":
+            if not _is_v2000_compatible(
+                atoms.array_length(), atoms.bonds.get_bond_count()
+            ):
+                raise ValueError(
+                    "The given number of atoms or bonds is too large for V2000 format"
+                )
+            return _write_structure_to_ctab_v2000(atoms, default_bond_type)
+        case "V3000":
+            return _write_structure_to_ctab_v3000(atoms, default_bond_type)
+        case unkown_version:
+            raise ValueError(f"Unknown CTAB version '{unkown_version}'")
+
+
+def _read_structure_from_ctab_v2000(ctab_lines):
+    n_atoms, n_bonds = _get_counts_v2000(ctab_lines[0])
+    atom_lines = ctab_lines[1 : 1 + n_atoms]
+    bond_lines = ctab_lines[1 + n_atoms : 1 + n_atoms + n_bonds]
+    charge_lines = [
+        line
+        for line in ctab_lines[1 + n_atoms + n_bonds :]
+        if line.startswith("M  CHG")
+    ]
+
+    atoms = AtomArray(n_atoms)
+    atoms.add_annotation("charge", int)
+    for i, line in enumerate(atom_lines):
+        atoms.coord[i, 0] = float(line[0:10])
+        atoms.coord[i, 1] = float(line[10:20])
+        atoms.coord[i, 2] = float(line[20:30])
+        atoms.element[i] = line[31:34].strip().upper()
+        # If one 'M CHG' entry is present,
+        # it supersedes all atom charges in the atom block
+        if not charge_lines:
+            charge = CHARGE_MAPPING.get(int(line[36:39]))
+            if charge is None:
+                warnings.warn(
+                    f"Cannot handle MDL charge type {int(line[36:39])}, "
+                    f"0 is used instead"
+                )
+                charge = 0
+            atoms.charge[i] = charge
+
+    for line in charge_lines:
+        # Remove 'M  CHGnn8' prefix
+        line = line[9:]
+        # The lines contains atom index and charge alternatingly
+        for atom_i_str, charge_str in _batched(line.split(), 2):
+            atom_index = int(atom_i_str) - 1
+            charge = int(charge_str)
+            atoms.charge[atom_index] = charge
+
+    bond_array = np.zeros((n_bonds, 3), dtype=np.uint32)
+    for i, line in enumerate(bond_lines):
+        bond_type = BOND_TYPE_MAPPING.get(int(line[6:9]))
+        if bond_type is None:
+            warnings.warn(
+                f"Cannot handle MDL bond type {int(line[6:9])}, "
+                f"BondType.ANY is used instead"
+            )
+            bond_type = BondType.ANY
+        bond_array[i, 0] = int(line[0:3]) - 1
+        bond_array[i, 1] = int(line[3:6]) - 1
+        bond_array[i, 2] = bond_type
+    atoms.bonds = BondList(n_atoms, bond_array)
+
+    return atoms
+
+
+def _read_structure_from_ctab_v3000(ctab_lines):
+    v30_lines = [line[6:].strip() for line in ctab_lines if line.startswith("M  V30")]
+
+    atom_lines = _get_block_v3000(v30_lines, "ATOM")
+    if len(atom_lines) == 0:
+        raise InvalidFileError("ATOM block is empty")
+    atoms = AtomArray(len(atom_lines))
+    atoms.add_annotation("charge", int)
+    # The V3000 atom index does not necessarily count from 1 to n,
+    # but allows arbitrary positive integers
+    # Hence, a mapping from V3000 atom index to AtomArray index is
+    # needed to get the correct index for a bond
+    v30_atom_indices = {}
+    for i, line in enumerate(atom_lines):
+        if "'" in line or '"' in line:
+            columns = shlex.split(line)
+        else:
+            columns = line.split()
+        v30_index = int(columns[0])
+        v30_type = columns[1]
+        if v30_type == "R#":
+            raise NotImplementedError("Rgroup atoms are not supported")
+        v30_coord = np.array(columns[2:5], dtype=float)
+        v30_properties = create_property_dict_v3000(columns[6:])
+
+        v30_atom_indices[v30_index] = i
+        atoms.coord[i] = v30_coord
+        atoms.element[i] = v30_type.upper()
+        atoms.charge[i] = int(v30_properties.get("CHG", 0))
+
+    bond_lines = _get_block_v3000(v30_lines, "BOND")
+    bond_array = np.zeros((len(bond_lines), 3), dtype=np.uint32)
+    for i, line in enumerate(bond_lines):
+        columns = line.split()
+        v30_type = int(columns[1])
+        v30_atom_index_1 = int(columns[2])
+        v30_atom_index_2 = int(columns[3])
+
+        bond_type = BOND_TYPE_MAPPING.get(v30_type)
+        if bond_type is None:
+            warnings.warn(
+                f"Cannot handle MDL bond type {v30_type}, BondType.ANY is used instead"
+            )
+            bond_type = BondType.ANY
+        bond_array[i, 0] = v30_atom_indices[v30_atom_index_1]
+        bond_array[i, 1] = v30_atom_indices[v30_atom_index_2]
+        bond_array[i, 2] = bond_type
+    atoms.bonds = BondList(atoms.array_length(), bond_array)
+
+    return atoms
+
+
+def _get_version(counts_line):
+    return counts_line[33:39].strip()
+
+
+def _is_v2000_compatible(n_atoms, n_bonds):
+    # The format uses a maximum of 3 digits for the atom and bond count
+    return n_atoms < 1000 and n_bonds < 1000
+
+
+def _get_counts_v2000(counts_line):
+    return int(counts_line[0:3]), int(counts_line[3:6])
+
+
+def _get_block_v3000(v30_lines, block_name):
+    block_lines = []
+    in_block = False
+    for line in v30_lines:
+        if line.startswith(f"BEGIN {block_name}"):
+            in_block = True
+        elif line.startswith(f"END {block_name}"):
+            if in_block:
+                return block_lines
+            else:
+                raise InvalidFileError(f"Block '{block_name}' ended before it began")
+        elif in_block:
+            block_lines.append(line)
+    return block_lines
+
+
+def create_property_dict_v3000(property_strings):
+    properties = {}
+    for prop in property_strings:
+        key, value = prop.split("=")
+        properties[key] = value
+    return properties
+
+
+def _write_structure_to_ctab_v2000(atoms, default_bond_type):
+    try:
+        charge = atoms.charge
+    except AttributeError:
+        charge = np.zeros(atoms.array_length(), dtype=int)
+
+    counts_line = (
+        f"{atoms.array_length():>3d}{atoms.bonds.get_bond_count():>3d}"
+        "  0     0  0  0  0  0  0  1 V2000"
+    )
+
+    for i, coord_name in enumerate(["x", "y", "z"]):
+        n_coord_digits = number_of_integer_digits(atoms.coord[:, i])
+        if n_coord_digits > 5:
+            raise BadStructureError(
+                f"5 pre-decimal columns for {coord_name}-coordinates are "
+                f"available, but array would require {n_coord_digits}"
+            )
+    atom_lines = [
+        f"{atoms.coord[i, 0]:>10.4f}"
+        f"{atoms.coord[i, 1]:>10.4f}"
+        f"{atoms.coord[i, 2]:>10.4f}"
+        f" {atoms.element[i].capitalize():3}"
+        f"{0:>2}"  # Mass difference -> unused
+        f"{CHARGE_MAPPING_REV.get(charge[i], 0):>3d}"
+        + f"{0:>3d}"
+        * 10  # More unused fields
+        for i in range(atoms.array_length())
+    ]
+
+    default_bond_value = BOND_TYPE_MAPPING_REV[default_bond_type]
+    bond_lines = [
+        f"{i + 1:>3d}{j + 1:>3d}"
+        f"{BOND_TYPE_MAPPING_REV.get(bond_type, default_bond_value):>3d}"
+        + f"{0:>3d}"
+        * 4
+        for i, j, bond_type in atoms.bonds.as_array()
+    ]
+
+    # V2000 files introduce charge annotations in the property block
+    # They define the charge literally (without mapping)
+    charge_lines = []
+    # Each `M  CHG` line can contain up to 8 charges
+    for batch in _batched(
+        [(atom_i, c) for atom_i, c in enumerate(charge) if c != 0], N_CHARGES_PER_LINE
+    ):
+        charge_lines.append(
+            f"M  CHG{len(batch):>3d}"
+            + "".join(f" {atom_i + 1:>3d} {c:>3d}" for atom_i, c in batch)
+        )
+
+    return [counts_line] + atom_lines + bond_lines + charge_lines + ["M  END"]
+
+
+def _write_structure_to_ctab_v3000(atoms, default_bond_type):
+    try:
+        charges = atoms.charge
+    except AttributeError:
+        charges = np.zeros(atoms.array_length(), dtype=int)
+
+    counts_line = f"COUNTS {atoms.array_length()} {atoms.bonds.get_bond_count()} 0 0 0"
+
+    for i, coord_name in enumerate(["x", "y", "z"]):
+        n_coord_digits = number_of_integer_digits(atoms.coord[:, i])
+        if n_coord_digits > 5:
+            raise BadStructureError(
+                f"5 pre-decimal columns for {coord_name}-coordinates are "
+                f"available, but array would require {n_coord_digits}"
+            )
+    atom_lines = [
+        f"{i + 1}"
+        f" {_quote(atoms.element[i].capitalize())}"
+        f" {atoms.coord[i, 0]:.4f}"
+        f" {atoms.coord[i, 1]:.4f}"
+        f" {atoms.coord[i, 2]:.4f}"
+        # 'aamap' is unused
+        f" 0"
+        f" {_to_property(charges[i])}"
+        for i in range(atoms.array_length())
+    ]
+
+    default_bond_value = BOND_TYPE_MAPPING_REV[default_bond_type]
+    bond_lines = [
+        f"{k + 1}"
+        f" {BOND_TYPE_MAPPING_REV.get(bond_type, default_bond_value)}"
+        f" {i + 1}"
+        f" {j + 1}"
+        for k, (i, j, bond_type) in enumerate(atoms.bonds.as_array())
+    ]
+
+    lines = (
+        ["BEGIN CTAB"]
+        + [counts_line]
+        + ["BEGIN ATOM"]
+        + atom_lines
+        + ["END ATOM"]
+        + ["BEGIN BOND"]
+        + bond_lines
+        + ["END BOND"]
+        + ["END CTAB"]
+    )
+    # Mark lines as V3000 CTAB
+    lines = ["M  V30 " + line for line in lines]
+    return [V2000_COMPATIBILITY_LINE] + lines + ["M  END"]
+
+
+def _to_property(charge):
+    if charge == 0:
+        return ""
+    else:
+        return f"CHG={charge}"
+
+
+def _quote(string):
+    if " " in string or len(string) == 0:
+        return f'"{string}"'
+    else:
+        return string
+
+
+def _batched(iterable, n):
+    """
+    Equivalent to :func:`itertools.batched()`.
+
+    However, :func:`itertools.batched()` is available since Python 3.12.
+    This function can be removed when the minimum supported Python
+    version is 3.12.
+    """
+    iterator = iter(iterable)
+    while batch := tuple(itertools.islice(iterator, n)):
+        yield batch

biotite/structure/io/mol/header.py

@@ -0,0 +1,120 @@
+# This source code is part of the Biotite package and is distributed
+# under the 3-Clause BSD License. Please see 'LICENSE.rst' for further
+# information.
+
+__name__ = "biotite.structure.io.mol"
+__author__ = "Patrick Kunzmann"
+__all__ = ["Header"]
+
+import datetime
+import warnings
+from dataclasses import dataclass
+
+_DATE_FORMAT = "%m%d%y%H%M"
+
+
+@dataclass
+class Header:
+    """
+    The header for connection tables.
+
+    Parameters
+    ----------
+    mol_name : str, optional
+        The name of the molecule.
+    initials : str, optional
+        The author's initials. Maximum length is 2.
+    program : str, optional
+        The program name. Maximum length is 8.
+    time : datetime or date, optional
+        The time of file creation.
+    dimensions : str, optional
+        Dimensional codes. Maximum length is 2.
+    scaling_factors : str, optional
+        Scaling factors. Maximum length is 12.
+    energy : str, optional
+        Energy from modeling program. Maximum length is 12.
+    registry_number : str, optional
+        MDL registry number. Maximum length is 6.
+    comments : str, optional
+        Additional comments.
+
+    Attributes
+    ----------
+    mol_name, initials, program, time, dimensions, scaling_factors, energy, registry_number, comments
+        Same as the parameters.
+    """
+
+    mol_name: ... = ""
+    initials: ... = ""
+    program: ... = ""
+    time: ... = None
+    dimensions: ... = ""
+    scaling_factors: ... = ""
+    energy: ... = ""
+    registry_number: ... = ""
+    comments: ... = ""
+
+    @staticmethod
+    def deserialize(text):
+        lines = text.splitlines()
+
+        mol_name = lines[0].strip()
+        initials = lines[1][0:2].strip()
+        program = lines[1][2:10].strip()
+        time_string = lines[1][10:20]
+        if time_string.strip() == "":
+            time = None
+        else:
+            try:
+                time = datetime.datetime.strptime(time_string, _DATE_FORMAT)
+            except ValueError:
+                warnings.warn(f"Invalid time format '{time_string}' in file header")
+                time = None
+        dimensions = lines[1][20:22].strip()
+        scaling_factors = lines[1][22:34].strip()
+        energy = lines[1][34:46].strip()
+        registry_number = lines[1][46:52].strip()
+
+        comments = lines[2].strip()
+
+        return Header(
+            mol_name,
+            initials,
+            program,
+            time,
+            dimensions,
+            scaling_factors,
+            energy,
+            registry_number,
+            comments,
+        )
+
+    def serialize(self):
+        text = ""
+
+        if self.time is None:
+            time_str = ""
+        else:
+            time_str = self.time.strftime(_DATE_FORMAT)
+
+        if len(self.mol_name) > 80:
+            raise ValueError("Molecule name must not exceed 80 characters")
+        text += str(self.mol_name) + "\n"
+        # Fixed columns -> minimum and maximum length is the same
+        # Shorter values are padded, longer values are truncated
+        text += (
+            f"{self.initials:>2.2}"
+            f"{self.program:>8.8}"
+            f"{time_str:>10.10}"
+            f"{self.dimensions:>2.2}"
+            f"{self.scaling_factors:>12.12}"
+            f"{self.energy:>12.12}"
+            f"{self.registry_number:>6.6}"
+            "\n"
+        )
+        text += str(self.comments) + "\n"
+        return text
+
+    def __str__(self):
+        return self.serialize()

biotite/structure/io/mol/mol.py

@@ -0,0 +1,149 @@
+# This source code is part of the Biotite package and is distributed
+# under the 3-Clause BSD License. Please see 'LICENSE.rst' for further
+# information.
+
+__name__ = "biotite.structure.io.mol"
+__author__ = "Patrick Kunzmann"
+__all__ = ["MOLFile"]
+
+from biotite.file import InvalidFileError, TextFile
+from biotite.structure.bonds import BondType
+from biotite.structure.io.mol.ctab import (
+    read_structure_from_ctab,
+    write_structure_to_ctab,
+)
+from biotite.structure.io.mol.header import Header
+
+# Number of header lines
+N_HEADER = 3
+
+
+class MOLFile(TextFile):
+    """
+    This class represents a file in MOL format, that is used to store
+    structure information for small molecules.
+    :footcite:`Dalby1992`
+
+    Since its use is intended for single small molecules, it stores
+    less atom annotation information than the macromolecular structure
+    formats:
+    Only the atom positions, charges, elements and bonds can be read
+    from the file, chain and and residue information is missing.
+
+    This class can also be used to parse the first structure from an SDF
+    file, as the SDF format extends the MOL format.
+
+    Attributes
+    ----------
+    header : Header
+        The header of the MOL file.
+
+    References
+    ----------
+
+    .. footbibliography::
+
+    Examples
+    --------
+
+    >>> from os.path import join
+    >>> mol_file = MOLFile.read(join(path_to_structures, "molecules", "TYR.sdf"))
+    >>> atom_array = mol_file.get_structure()
+    >>> print(atom_array)
+                0             N         1.320    0.952    1.428
+                0             C        -0.018    0.429    1.734
+                0             C        -0.103    0.094    3.201
+                0             O         0.886   -0.254    3.799
+                0             C        -0.274   -0.831    0.907
+                0             C        -0.189   -0.496   -0.559
+                0             C         1.022   -0.589   -1.219
+                0             C        -1.324   -0.102   -1.244
+                0             C         1.103   -0.282   -2.563
+                0             C        -1.247    0.210   -2.587
+                0             C        -0.032    0.118   -3.252
+                0             O         0.044    0.420   -4.574
+                0             O        -1.279    0.184    3.842
+                0             H         1.977    0.225    1.669
+                0             H         1.365    1.063    0.426
+                0             H        -0.767    1.183    1.489
+                0             H         0.473   -1.585    1.152
+                0             H        -1.268   -1.219    1.134
+                0             H         1.905   -0.902   -0.683
+                0             H        -2.269   -0.031   -0.727
+                0             H         2.049   -0.354   -3.078
+                0             H        -2.132    0.523   -3.121
+                0             H        -0.123   -0.399   -5.059
+                0             H        -1.333   -0.030    4.784
+    """
+
+    def __init__(self):
+        super().__init__()
+        # empty header lines
+        self.lines = [""] * N_HEADER
+        self._header = None
+
+    @classmethod
+    def read(cls, file):
+        mol_file = super().read(file)
+        mol_file._header = None
+        return mol_file
+
+    @property
+    def header(self):
+        if self._header is None:
+            self._header = Header.deserialize("\n".join(self.lines[0:3]) + "\n")
+        return self._header
+
+    @header.setter
+    def header(self, header):
+        self._header = header
+        self.lines[0:3] = self._header.serialize().splitlines()
+
+    def get_structure(self):
+        """
+        Get an :class:`AtomArray` from the MOL file.
+
+        Returns
+        -------
+        array : AtomArray
+            This :class:`AtomArray` contains the optional ``charge``
+            annotation and has an associated :class:`BondList`.
+            All other annotation categories, except ``element`` are
+            empty.
+        """
+        ctab_lines = _get_ctab_lines(self.lines)
+        if len(ctab_lines) == 0:
+            raise InvalidFileError("File does not contain structure data")
+        return read_structure_from_ctab(ctab_lines)
+
+    def set_structure(self, atoms, default_bond_type=BondType.ANY, version=None):
+        """
+        Set the :class:`AtomArray` for the file.
+
+        Parameters
+        ----------
+        atoms : AtomArray
+            The array to be saved into this file.
+            Must have an associated :class:`BondList`.
+        default_bond_type : BondType, optional
+            Bond type fallback for the *Bond block*, if a
+            :class:`BondType` has no CTAB counterpart.
+            By default, each such bond is treated as
+            :attr:`BondType.ANY`.
+        version : {"V2000", "V3000"}, optional
+            The version of the CTAB format.
+            ``"V2000"`` uses the *Atom* and *Bond* block, while
+            ``"V3000"`` uses the *Properties* block.
+            By default, ``"V2000"`` is used, unless the number of atoms
+            or bonds exceeds 999, in which case ``"V3000"`` is used.
+        """
+        self.lines = self.lines[:N_HEADER] + write_structure_to_ctab(
+            atoms, default_bond_type, version
+        )
+
+
+def _get_ctab_lines(lines):
+    for i, line in enumerate(lines):
+        if line.startswith("M  END"):
+            return lines[N_HEADER : i + 1]
+    return lines[N_HEADER:]