diff --git a/openff/recharge/charges/bcc.py b/openff/recharge/charges/bcc.py index 4551b80..65ac33b 100644 --- a/openff/recharge/charges/bcc.py +++ b/openff/recharge/charges/bcc.py @@ -1,5 +1,4 @@ """Generate bond charge corrections for molecules from a collection of BCC parameters.""" -import json import os from typing import TYPE_CHECKING, Any, Dict, List, Optional @@ -454,19 +453,14 @@ def original_am1bcc_corrections() -> BCCCollection: 23(16), 1623–1641. 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+ + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + \ No newline at end of file diff --git a/scripts/convert-am1-bcc/convert_bccs_to_offxml.py b/scripts/convert-am1-bcc/convert_bccs_to_offxml.py new file mode 100644 index 0000000..f48104d --- /dev/null +++ b/scripts/convert-am1-bcc/convert_bccs_to_offxml.py @@ -0,0 +1,53 @@ +import click + +from openff.toolkit import ForceField +from openff.units import unit +from openff.recharge.charges.bcc import BCCCollection + + +@click.command() +@click.option( + "--input-file", + default="openeye-am1-bcc.json", + type=click.Path(exists=True, dir_okay=False, file_okay=True), + help="Input BCC collection (JSON)" +) +@click.option( + "--output-file", + default="openeye-am1-bcc.offxml", + type=click.Path(exists=False, dir_okay=False, file_okay=True), + help="Output BCC force field (offxml)" +) +@click.option( + "--partial-charge-method", + default="AM1-Mulliken", + type=click.Choice(["zeros", "AM1-Mulliken"]), + help=( + "Charge method to use in combination with the BCCs. " + "Use 'zeros' for debugging, 'AM1-Mulliken' for production." + ) +) +def convert_bccs_to_offxml( + input_file, + output_file, + partial_charge_method, +): + collection = BCCCollection.parse_file(input_file) + ff = ForceField() + + ff.get_parameter_handler("Electrostatics") + handler = ff.get_parameter_handler("ChargeIncrementModel") + handler.partial_charge_method = partial_charge_method + + for parameter in collection.parameters[::-1]: + handler.add_parameter({ + "smirks": parameter.smirks, + "charge_increment": [parameter.value * unit.elementary_charge], + "id": parameter.provenance["code"] + }) + + ff.to_file(output_file) + + +if __name__ == "__main__": + convert_bccs_to_offxml() diff --git a/scripts/convert-am1-bcc/generate_original_am1bcc.py b/scripts/convert-am1-bcc/generate_original_am1bcc.py new file mode 100644 index 0000000..b700558 --- /dev/null +++ b/scripts/convert-am1-bcc/generate_original_am1bcc.py @@ -0,0 +1,306 @@ +"""This script converts the original AM1BCC values [1]_ into the data model expected by +this framework. + +References +---------- +[1] Jakalian, A., Jack, D. B., & Bayly, C. I. (2002). Fast, efficient generation of + high-quality atomic charges. AM1-BCC model: II. Parameterization and validation. + Journal of computational chemistry, 23(16), 1623–1641. +""" +import click +import json +import itertools +import logging + +import numpy as np +import pandas as pd +from openeye import oechem + +from openff.recharge.charges.bcc import BCCParameter + +logging.basicConfig() +logger = logging.getLogger(__name__) + + +GENERAL_ATOM_CODES = { + # from more general to more specific + # patterns will get matched with more specific ones so order is important! + "X": { + # === HALOGENS === + # F1 Fluorine + "71": [r"[#9:1]"], + # Cl1 Chlorine + "72": [r"[#17:1]"], + # Br1 Bromine + "73": [r"[#35:1]"], + # I1 Iodine + "74": [r"[#53:1]"], + # === OTHER === + # Si4 Tetravalent silicon + "61": [r"[#14X4:1]"], + # H1 Hydrogen + "91": [r"[#1:1]"], + }, + "S": { + # === SULFUR === + # S1,2 Univalent or divalent sulfur + "51": [r"[#16X1:1]", "[#16X2:1]"], + # S3 Trivalent sulfur + "52": [r"[#16X3:1]"], + # S4 Tetravalent sulfur + "53": [r"[#16X4:1]"], + }, + "P": { + # === PHOSPHORUS === + # P2,3 Divalent or trivalent phosphorus + # "41": [r"[#15:1]", "[#15X2:1]", "[15X1:1]", "[#15X3:1]"], + "41": [r"[#15:1]"], + # P3,4 Trivalent or tetravalent double-bonded phosphorus + # "42": [r"[15X4:1]", "[#15X3;$(*=[*]):1]"], + "42": [r"[#15X4,#15X3$(*=[*]):1]"], + }, + "O": { + # === OXYGEN === + # O1,2 Univalent or divalent oxygen + # "31": [r"[#8:1]", "[#8X1:1]", "[#8X2:1]"], + "31": [r"[#8:1]"], + # O1ester,acid Double-bonded oxygen in an ester or acid + "32": [r"[#8X1$(*=[#6X3]-[#8X2]):1]"], + # O1lact Double-bonded oxygen in a lactone or lactam + "33": [r"[#8X1$(*=[#6r]@[#7r,#8r]):1]"], + }, + "C": { + # === CARBON === + # C4 Tetravalent carbon + "11": [r"[#6X4:1]"], + # C1,2 Univalent or divalent carbon + "15": [r"[#6X1:1]", "[#6X2:1]"], + # C3=C Trivalent carbon, double bonded to carbon + "12": [r"[#6X3:1]"], + # Car Aromatic carbon + "16": [ + r"[#6a:1]", + # or planar ring with two continuous single bonds and at least two double bonds + r"[#6X3R$([*](-,:[R]-,=,:[R])=,:[R]):1]", + ], + # Carlp Aromatic carbon bonded to an aromatic oxygen or nitrogen with a lone pair + "17": [ + r"[#6aX3$(*~[#7aX2,#8aX2]):1]", + r"[#6X3R$(*~[#7aX2,#8aX2])&$([*](-,:[R]-,=,:[R])=,:[R]):1]", + ], + # C3=N,P Trivalent carbon, double bonded to nitrogen or phosphorus + "13": [ + r"[#6X3$(*=[#7,#15]):1]", + ], + # C3=O,S Trivalent carbon, double bonded to oxygen or sulfur + "14": [r"[#6X3$(*=[#8X1,#8X2+1,#16+0]):1]"], + "12b": [r"[#6X3A$(*=[#6]):1]"], + }, + "N": { + # === NITROGEN === + # N1,2 Univalent or cationic divalent nitrogen + "25": [r"[#7:1]", r"[#7X1,#7X2+1:1]"], + # N2 Neutral divalent nitrogen + "24": [r"[#7X2+0,#7X2-1ar5:1]"], + # N2,3,4 Amine nitrogen + "21": [ + r"[#7X4:1]", + r"[#7X3:1]", + r"[#7X2-1A:1]", + ], # "[#7X2$([*](-,:[*])-,:[*]):1]"], + # N3deloc Trivalent nitrogen with a delocalized lone pair + "22": [ + r"[#7X2$(*(-,:[*])-,:[#6X3$(*=[#8,#16])]):1]", # N2-C(=O,S), + ], + "23": [ + r"[#7X3r5$([*](-,:[r5])(-,:[r5])-[!#1&!#6X4&!#6a]):1]", + # "[#7X3R$([*](-[!#1&!])(-,:[R]=,:[R])-,:[R]=,:[R]):1]", + r"[#7X3r5$([*]1(-,:[r5]=,:[r5]-,:[r5]=,:[r5]:,-1)-[!#1&!#6a!#6X4]):1]", + r"[#7X3+1:1]", + r"[#7X3$([*](~[#8X1])~[#8X1]):1]", + # "[#7X3$([*]~[#7X2]=[#7X3]):1]", + r"[#7X3+0$(*-[#6X3$(*=[#7X3+1])]):1]", + ], + "22b": [ + r"[#7X3+0$(*-[#6X3$(*(=,:[#8,#16])-[!#8&!#16])]):1]", # amide + # "[#7X3+0$(*-[#6X3$(*(=[#8X2+1]-[#7X2-1])-[!#8&!#16])]):1]", + ], + "23b": [ + r"[#7X3ar5:1]", + ], + }, +} + +SPECIFIC_PATTERNS = { + # P-O + r"[#8X1-1:1]~[#15&!$(*=*):2]": "310941", + r"[#8X2:1]-[#15X4+0,#15X3;!$(*=*):2]": "310141", + r"[#8X1:1]-,=[#15X4$([*](-[#8X1-1])-[#8X1-1,#8X2,#16X2]):2]": "310942", + r"[#8X1-1:1]-[#15X4$([*](=[#8X1])-[#8X1-1]):2]": "310942", + r"[#8X1-1:1]-,:[#15X4$([*](-[#8X1-1])(-[#8X1-1])=[#8]):2]": "310942", + r"[#8X1:1]=[#15X4$([*](-[#8X1-1])(-[#6])-[#6,#1]):2]": "310942", + # ... + # 'Delocalised' S-O + r"[#16X1,#16X2;$(*=[#8X1]);$(*-[#8X1-1]):2]~[#8X1:1]": "310951", + r"[#16X3$(*=[#8X1]);$(*-[#8X1-1]):2]~[#8X1:1]": "310952", + r"[#16X4$(*~[#8X1]);$(*-[#8X1-1]):2]~[#8X1:1]": "310953", + # 'Delocalised' S-S + r"[#16X1-1$([*]-S),#16X1+0$([*]=S):1]-,=[#16X4:2]": "510953", + # 'Delocalised' S-C + r"[#6a:1]-[#16X1-1:2]": "160951", + r"[#6a$(*~[#7aX2,#8aX2]):1]-[#16X1-1:2]": "170951", + r"[#6X3:1](~[#8X1,#16X1])(~[#16X1:2])": "140951", + r"[#6X3$(*=[#7,#15]):1]-[#16X1-1:2]": "130951", + r"[#6X3$(*=[#6]):1]-[#16X1-1:2]": "120951", + r"[#6X1,#6X2:1]-[#16X1-1:2]": "150951", + r"[#6X1,#6X2$([*]=[#8,#16]):1]=[#16:2]": "150951", + r"[#6X4:1]-[#16X1-1:2]": "110951", + # 'Delocalised' C-O + r"[#6a:1]-[#8X1-1:2]": "160931", + r"[#6a$(*~[#7aX2,#8aX2]):1]-[#8X1-1:2]": "170931", + r"[#6X3:1](~[#8X1,#16X1])(~[#8X1:2])": "140931", + r"[#6X3$(*=[#7,#15]):1]-[#8X1-1:2]": "130931", + r"[#6X3$(*=[#6]):1]-[#8X1-1:2]": "120931", + r"[#6X1,#6X2:1]-[#8X1-1:2]": "150931", + r"[#6X2$([*]=[#8,#16]):1]=[#8X1:2]": "150931", + r"[#6X4:1]-[#8X1-1:2]": "110931", + # 'Delocalised' N-O + r"[#7X2+0:1]-[#8X1-1:2]": "240631", + r"[#7X3+1:1]-[#8X1-1:2]": "230631", + ( + r"[#7X4+1,#7X3+0$([*]-[#6X3]=,:[#7X2,#6X3]),#7X3+0$([*]-[#6X3]-,=,:[#7a,#6a])," + r"#7X3+0$(*-[#6X4,#1]),#7X3+0$([*](-[#7X3])-[#7X3])," + r"#7X3+0$([*](-[#8])-[#8]):1]-[#8X1-1:2]" + ): "210631", + r"[#7X3+0$(*-[#6X3$(*=[#8,#16])]):1]-[#8X1-1:2]": "220631", + ( + r"[$([#7X3](-[#8X1])=[#8X1]),$([#7X3](=[#8X1])=[#8X1])," + r"$([#7X3](-[#8X1])-[#8X1]):1]~[#8X1:2]" + ): "230931", +} + +GENERAL_BOND_CODES = { + "09": "~", # Single bond with charge or delocalized bond + "08": ":", # 'Double' aromatic Bond + "07": ":", # 'Single' aromatic Bond + "06": "-", # 'Single' Dative bond + "03": "#", # Triple bond + "02": "=", # Double bond + "01": "-", # Single bond +} + +BCC_OVERRIDES = { + "110112": 0.0024, + "120114": -0.0172, +} + + +def build_bccs( + bcc_value_file: str = "am1bcc.csv", +): + bcc_frame = pd.read_csv(bcc_value_file) + bcc_frame[r"Code"] = bcc_frame[r"Code"].astype(str) + bcc_frame[r"BCC"] = bcc_frame[r"BCC"].round(4) + + BCC_VALUES = dict(zip(bcc_frame[r"Code"], bcc_frame[r"BCC"])) + BCC_VALUES.update(BCC_OVERRIDES) + + flat_atom_codes = {} + for element_smirks in GENERAL_ATOM_CODES.values(): + for atom_code, all_atom_smirks in element_smirks.items(): + not_atom_map = [smirks[1:-3] for smirks in all_atom_smirks] + final_smirks = f"[{','.join(not_atom_map)}:1]" + flat_atom_codes[final_smirks] = atom_code[:2] + + # create bcc patterns from less to more specific + bcc_patterns = [] + for (atom_smirks1, atom_code1), ( + atom_smirks2, + atom_code2, + ) in itertools.combinations_with_replacement(flat_atom_codes.items(), 2): + for bond_code, bond_smirks in GENERAL_BOND_CODES.items(): + smirks = atom_smirks1 + bond_smirks + atom_smirks2.replace(":1", ":2") + code = atom_code1 + bond_code + atom_code2 + bcc_patterns.append((smirks, code)) + + if atom_smirks2 != atom_smirks1: + smirks2 = atom_smirks2 + bond_smirks + atom_smirks1.replace(":1", ":2") + code2 = atom_code2 + bond_code + atom_code1 + bcc_patterns.append((smirks2, code2)) + + for smirks, code in SPECIFIC_PATTERNS.items(): + bcc_patterns.append((smirks, code)) + + # create BCCs from more to less specific + bond_charge_corrections = [] + unique_patterns = set() + for smirks, code in bcc_patterns[::-1]: + if smirks in unique_patterns: + continue + if code not in BCC_VALUES: + if code[:2] == code[-2:]: + value = 0 + else: + continue + else: + value = BCC_VALUES[code] + + # Validate the smirks + query = oechem.OEQMol() + assert oechem.OEParseSmarts(query, smirks) + + bcc = BCCParameter(smirks=smirks, value=value, provenance={"code": code}) + bond_charge_corrections.append(bcc) + unique_patterns.add(smirks) + + # TODO: reverse if we reverse the order of BCCs to go from less to more specific + return bond_charge_corrections[::-1] + + +@click.command() +@click.option( + "--bcc-value-file", + default="am1bcc.csv", + help="The name of the file containing the BCC values.", +) +@click.option( + "--output-file", + default="openeye-am1-bcc.json", + help="The name of the output file to write the BCCs to.", +) +def create_openeye_bccs( + bcc_value_file: str = "am1bcc.csv", + output_file: str = "openeye-am1-bcc.json", +): + bcc_parameters = build_bccs(bcc_value_file=bcc_value_file) + + # Remove duplicate parameters caused by the duplication of the aromatic + # bond type. + bcc_parameters_per_smirks = {} + unique_bcc_parameters = [] + + for bcc_parameter in bcc_parameters: + if bcc_parameter.smirks in bcc_parameters_per_smirks: + code = bcc_parameter.provenance[r"code"] + assert np.isclose( + bcc_parameter.value, + bcc_parameters_per_smirks[bcc_parameter.smirks].value, + ), (bcc_parameter, bcc_parameters_per_smirks[bcc_parameter.smirks]) + is_aromatic = code[2:4] in [r"07", "08"] + is_self_to_self = code[:2] == code[-2:] + assert is_aromatic or is_self_to_self, bcc_parameter + continue + unique_bcc_parameters.append(bcc_parameter) + bcc_parameters_per_smirks[bcc_parameter.smirks] = bcc_parameter + + with open(output_file, "w") as f: + json.dump( + # reverse for now while recharge still goes from more to less specific + {"parameters": [bcc.dict() for bcc in bcc_parameters][::-1]}, + f, + indent=4, + ) + + +if __name__ == "__main__": + create_openeye_bccs() diff --git a/scripts/convert-am1-bcc/convert.py b/scripts/convert-am1-bcc/legacy/convert.py similarity index 100% rename from scripts/convert-am1-bcc/convert.py rename to scripts/convert-am1-bcc/legacy/convert.py diff --git a/scripts/convert-am1-bcc/legacy/original-am1-bcc.json b/scripts/convert-am1-bcc/legacy/original-am1-bcc.json new file mode 100644 index 0000000..7b85542 --- /dev/null +++ b/scripts/convert-am1-bcc/legacy/original-am1-bcc.json @@ -0,0 +1 @@ +[{"smirks": "[#6X4:1]-[#16X1-1:2]", "value": 0.0833, "provenance": {"code": "110951"}}, {"smirks": "[#6X1,#6X2:1]-[#16X1-1:2]", "value": 0.3281, "provenance": {"code": "150951"}}, {"smirks": "[#6X3$(*=[#6]):1]-[#16X1-1:2]", "value": 0.1879, "provenance": {"code": "120951"}}, {"smirks": "[#6X3$(*=[#7,#15]):1]-[#16X1-1:2]", "value": 0.1969, "provenance": {"code": "130951"}}, {"smirks": "[#6X3:1](~[#8X1,#16X1])(~[#16X1:2])", "value": 0.1713, "provenance": {"code": "140951"}}, {"smirks": "[#6a$(*~[#7aX2,#8aX2]):1]-[#16X1-1:2]", "value": 0.3476, "provenance": {"code": "170951"}}, {"smirks": "[#6a:1]-[#16X1-1:2]", "value": 0.2541, "provenance": {"code": "160951"}}, {"smirks": "[$([#7X3](-[#8X1])=[#8X1]),$([#7X3](=[#8X1])=[#8X1]):1]~[#8X1:2]", "value": -0.15, "provenance": {"code": "230931"}}, {"smirks": "[#7X3+1:1]-[#8X1-1:2]", "value": 0.1317, "provenance": {"code": "230631"}}, {"smirks": "[#7X3$(*-[#6X3$(*=[#8])]):1]-[#8X1-1:2]", "value": 0.0465, "provenance": {"code": "220631"}}, {"smirks": "[#7X4+1:1]-[#8X1-1:2]", "value": -0.1168, "provenance": {"code": "210631"}}, {"smirks": "[#7X1,#7X2+1:1]-[#8X1-1:2]", "value": -0.0543, "provenance": {"code": "250631"}}, {"smirks": "[#7X2+0:1]-[#8X1-1:2]", "value": -0.0817, "provenance": {"code": "240631"}}, {"smirks": "[#6X4:1]-[#8X1-1:2]", "value": 0.1615, "provenance": {"code": "110931"}}, {"smirks": "[#6X1,#6X2:1]-[#8X1-1:2]", "value": 0.2549, "provenance": {"code": "150931"}}, {"smirks": "[#6X3$(*=[#6]):1]-[#8X1-1:2]", "value": 0.1844, "provenance": {"code": "120931"}}, {"smirks": "[#6X3$(*=[#7,#15]):1]-[#8X1-1:2]", "value": 0.3046, "provenance": {"code": "130931"}}, {"smirks": "[#6X3:1](~[#8X1,#16X1])(~[#8X1:2])", "value": 0.2653, "provenance": {"code": "140931"}}, {"smirks": "[#6a$(*~[#7aX2,#8aX2]):1]-[#8X1-1:2]", "value": 0.337, "provenance": {"code": "170931"}}, {"smirks": "[#6a:1]-[#8X1-1:2]", "value": 0.2797, "provenance": {"code": "160931"}}, {"smirks": "[#6X4:1]-[#6X4:2]", "value": 0.0, "provenance": {"code": "110111"}}, {"smirks": "[#6X4:1]-[#6X1,#6X2:2]", "value": -0.0269, "provenance": {"code": "110115"}}, {"smirks": "[#6X4:1]-[#6X3$(*=[#6]):2]", "value": 0.0024, "provenance": {"code": "110112"}}, {"smirks": "[#6X4:1]-[#6X3$(*=[#7,#15]):2]", "value": -0.0753, "provenance": {"code": "110113"}}, {"smirks": "[#6X4:1]-[#6X3$(*=[#8,#16]):2]", "value": -0.05, "provenance": {"code": "110114"}}, {"smirks": "[#6X4:1]-[#6a$(*~[#7aX2,#8aX2]):2]", "value": -0.0943, "provenance": {"code": "110117"}}, {"smirks": "[#6X4:1]-[#6a:2]", "value": 0.0073, "provenance": {"code": "110116"}}, {"smirks": "[#6X4:1]-[#7X3ar5,#7X3+1,#7X3+0$(*-[#6X3$(*=[#7X3+1])]),$([#7X3](-[#8X1-1])=[#8X1]),$([#7X3](=[#8X1])=[#8X1]):2]", "value": -0.0193, "provenance": {"code": "110123"}}, {"smirks": "[#6X4:1]-[#7X2-1$(*-[#6X3$(*=[#8X1,#16X1])]),#7X3$(*-[#6X3$(*=[#8X1,#16X1])]):2]", "value": 0.0374, "provenance": {"code": "110122"}}, {"smirks": "[#6X4:1]-[#7X4,#7X3,#7X2-1:2]", "value": 0.1582, "provenance": {"code": "110121"}}, {"smirks": "[#6X4:1]-[#7X1,#7X2+1:2]", "value": 0.1825, "provenance": {"code": "110125"}}, {"smirks": "[#6X4:1]-[#7X2+0,#7X2-1ar5:2]", "value": 0.1252, "provenance": {"code": "110124"}}, {"smirks": 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