chemical-structure-converter（化学结构转换器）

Chemical Structure Converter

Interconvert between different chemical structure representations including IUPAC names, SMILES strings, molecular formulas, and common names. Essential for cheminformatics workflows, database standardization, and compound registration in drug discovery and chemical research.

Key Capabilities:

• Multi-Format Conversion: Convert between IUPAC names, SMILES, InChI, and molecular formulas
• SMILES Validation: Validate SMILES syntax for structural correctness
• Batch Processing: Process multiple compounds for database standardization
• Identifier Lookup: Retrieve all available identifiers for known compounds
• Structure Standardization: Normalize chemical representations for consistency

When to Use

✅ Use this skill when:

• Standardizing chemical databases with mixed naming conventions
• Preparing compound libraries for virtual screening or cheminformatics analysis
• Converting structures from publications (IUPAC names) to machine-readable formats (SMILES)
• Validating SMILES strings before using in computational chemistry tools
• Registering new compounds in chemical inventory systems
• Matching compounds across different databases with different identifier types
• Creating structure-activity relationship (SAR) tables with consistent formatting

❌ Do NOT use when:

• Needing 3D structure generation or conformer search → Use molecular modeling software (RDKit, OpenBabel)
• Performing quantum chemistry calculations → Use Gaussian, ORCA, or similar packages
• Working with reaction schemes or multi-step synthesis → Use reaction planning tools
• Requiring patent structure searching → Use specialized patent databases (SciFinder, STN)
• Converting biological sequences (DNA, protein) → Use bioinformatics tools
• Needing spectral data prediction (NMR, MS) → Use specialized prediction software

Related Skills:

• 上游 (Upstream): chemical-storage-sorter, adme-property-predictor
• 下游 (Downstream): molecular-docking-predictor, bio-ontology-mapper

Integration with Other Skills

Upstream Skills:

• chemical-storage-sorter: Classify chemicals by hazard group before storage registration
• adme-property-predictor: Convert structures to standardized formats before ADME prediction
• safety-data-sheet-reader: Extract chemical names from SDS for structure lookup

Downstream Skills:

• molecular-docking-predictor: Convert compound libraries to 3D structures for docking
• bio-ontology-mapper: Map chemical structures to standardized ontologies (ChEBI, PubChem)
• lab-inventory-tracker: Register standardized chemical identifiers in inventory

Complete Workflow:

Literature/Patent → chemical-structure-converter → adme-property-predictor → molecular-docking-predictor → Hit Selection

Core Capabilities

1. Multi-Format Chemical Identifier Conversion

Convert chemical structures between different representation formats for database interoperability.

from scripts.main import ChemicalStructureConverter

converter = ChemicalStructureConverter()

# Convert compound name to all available identifiers
chemical_name = "aspirin"
data = converter.name_to_identifiers(chemical_name)

if data:
    print(f"Compound: {chemical_name}")
    print(f"IUPAC Name: {data['iupac']}")
    print(f"SMILES: {data['smiles']}")
    print(f"Formula: {data['formula']}")
    print(f"Molecular Weight: {data['mw']} g/mol")

# Output:
# Compound: aspirin
# IUPAC Name: 2-acetoxybenzoic acid
# SMILES: CC(=O)Oc1ccccc1C(=O)O
# Formula: C9H8O4
# Molecular Weight: 180.16 g/mol

Supported Conversions:

Best Practices:

• ✅ Use canonical SMILES for database storage (ensures uniqueness)
• ✅ Validate conversions with known reference compounds
• ✅ Preserve stereochemistry during conversions (use @/@@ in SMILES)
• ✅ Check tautomeric forms - different representations may exist

Common Issues and Solutions:

Issue: Compound not in local database

• Symptom: Returns "Unknown structure" for valid compounds
• Solution: Use external databases (PubChem, ChemSpider APIs) for lookup; add common compounds to local database

Issue: Multiple valid SMILES for same compound

• Symptom: Different SMILES strings represent same molecule
• Solution: Use canonical SMILES generation (requires RDKit or similar)

2. SMILES String Validation

Validate SMILES syntax to ensure structural integrity before computational processing.

from scripts.main import ChemicalStructureConverter

converter = ChemicalStructureConverter()

# Validate SMILES strings
smiles_examples = [
    "CC(=O)Oc1ccccc1C(=O)O",  # Aspirin - valid
    "CCO",                     # Ethanol - valid
    "C(=O",                    # Invalid - unclosed parenthesis
    "C1CCCCC",                 # Invalid - unclosed ring
]

for smiles in smiles_examples:
    is_valid, message = converter.validate_smiles(smiles)
    status = "✅ Valid" if is_valid else "❌ Invalid"
    print(f"{smiles:<30} {status}: {message}")

# Output:
# CC(=O)Oc1ccccc1C(=O)O        ✅ Valid: Valid SMILES syntax
# CCO                          ✅ Valid: Valid SMILES syntax
# C(=O                         ❌ Invalid: Mismatched parentheses
# C1CCCCC                      ❌ Invalid: Ring closure error

Validation Checks:

Best Practices:

• ✅ Always validate SMILES before using in downstream tools
• ✅ Check for aromaticity (lowercase c,n,o in SMILES)
• ✅ Verify stereochemistry (@ symbols for chirality)
• ✅ Use explicit hydrogens when ambiguity exists

Common Issues and Solutions:

Issue: Valid syntax but chemically impossible

• Symptom: SMILES passes validation but structure is unrealistic
• Solution: Use chemical validation tools (RDKit SanitizeMol) for deeper checks

Issue: Tautomeric ambiguity

• Symptom: Keto/enol forms represented differently
• Solution: Use tautomer canonicalization if consistency required

3. Batch Structure Processing

Process multiple chemical structures simultaneously for database standardization.

from scripts.main import ChemicalStructureConverter

converter = ChemicalStructureConverter()

# Batch process compound list
compound_list = [
    "aspirin",
    "caffeine", 
    "glucose",
    "ethanol",
    "unknown_compound"
]

results = []
for compound in compound_list:
    data = converter.name_to_identifiers(compound)
    if data:
        results.append({
            'name': compound,
            'iupac': data['iupac'],
            'smiles': data['smiles'],
            'formula': data['formula'],
            'mw': data['mw']
        })
    else:
        print(f"⚠️  Warning: '{compound}' not found in database")

# Display results table
print("\
" + "="*80)
print(f"{'Name':<20} {'Formula':<15} {'MW':<10} {'SMILES'}")
print("="*80)
for r in results:
    print(f"{r['name']:<20} {r['formula']:<15} {r['mw']:<10.2f} {r['smiles'][:40]}")

Best Practices:

• ✅ Process in batches of 100-1000 for large databases
• ✅ Log missing compounds for manual review
• ✅ Export to CSV for Excel/chemoinformatics tools
• ✅ Include CAS numbers when available for verification

Common Issues and Solutions:

Issue: Synonym confusion

• Symptom: Same compound listed multiple times with different names
• Solution: Use SMILES as unique key; deduplicate by structure

Issue: Mixture or salt forms

• Symptom: Structures with counterions or multiple components
• Solution: Process main component; flag mixtures for special handling

4. Molecular Formula and Properties

Extract molecular formulas and calculate basic properties from SMILES or names.

from scripts.main import ChemicalStructureConverter

converter = ChemicalStructureConverter()

# Analyze compound properties
compounds = ["aspirin", "caffeine", "glucose"]

print("Molecular Properties:")
print("-" * 70)
print(f"{'Compound':<15} {'Formula':<12} {'MW (g/mol)':<12} {'Heavy Atoms'}")
print("-" * 70)

for name in compounds:
    data = converter.name_to_identifiers(name)
    if data:
        # Count heavy atoms (non-hydrogen) from formula
        formula = data['formula']
        heavy_atoms = sum(int(c) for c in formula if c.isdigit())
        if heavy_atoms == 0:  # Single atoms like C, O
            heavy_atoms = len([c for c in formula if c.isupper()])
        
        print(f"{name:<15} {data['formula']:<12} {data['mw']:<12.2f} {heavy_atoms}")

Calculated Properties:

Best Practices:

• ✅ Include salt forms in MW calculation if relevant
• ✅ Check isotopic labeling for specialized applications
• ✅ Calculate elemental composition for combustion analysis
• ✅ Use exact mass for mass spectrometry applications

Common Issues and Solutions:

Issue: Hydrates and solvates

• Symptom: Different MW for hydrate vs anhydrous forms
• Solution: Always specify form (e.g., "caffeine anhydrous")

5. Structure Standardization

Standardize chemical representations for database consistency.

from scripts.main import ChemicalStructureConverter

def standardize_compound_entry(name: str, converter) -> dict:
    """
    Standardize compound entry with all identifiers.
    
    Returns standardized entry or None if not found.
    """
    data = converter.name_to_identifiers(name)
    
    if not data:
        return None
    
    # Create standardized entry
    standardized = {
        'common_name': name.lower(),
        'iupac_name': data['iupac'],
        'smiles': data['smiles'],
        'inchi': f"InChI=1S/{data['formula']}",  # Placeholder
        'molecular_formula': data['formula'],
        'molecular_weight': data['mw'],
        'standardized_date': '2026-02-09',
        'source': 'local_database'
    }
    
    return standardized

# Example usage
converter = ChemicalStructureConverter()
entry = standardize_compound_entry("aspirin", converter)

if entry:
    print("Standardized Entry:")
    for key, value in entry.items():
        print(f"  {key}: {value}")

Standardization Rules:

Best Practices:

• ✅ Use consistent naming across entire database
• ✅ Include CAS numbers when available
• ✅ Track version history of structure assignments
• ✅ Validate against PubChem for known compounds

Common Issues and Solutions:

Issue: Multiple valid representations

• Symptom: Same compound has different standard forms
• Solution: Define canonicalization rules; use chemical validation

6. Chemical Database Integration

Prepare chemical data for import into cheminformatics databases.

import json
from scripts.main import ChemicalStructureConverter

def prepare_database_import(compound_names: list, converter) -> list:
    """
    Prepare compound list for database import.
    
    Returns list of standardized database records.
    """
    records = []
    
    for name in compound_names:
        data = converter.name_to_identifiers(name)
        
        if data:
            record = {
                'compound_id': f"CMPD_{len(records)+1:04d}",
                'common_name': name,
                'iupac_name': data['iupac'],
                'smiles': data['smiles'],
                'molecular_formula': data['formula'],
                'molecular_weight': data['mw'],
                'status': 'active'
            }
            records.append(record)
        else:
            print(f"⚠️  Skipped: {name} (not in database)")
    
    return records

# Generate database import file
converter = ChemicalStructureConverter()
compounds = ["aspirin", "caffeine", "glucose", "ethanol"]

db_records = prepare_database_import(compounds, converter)

# Export to JSON for database import
with open('chemical_database_import.json', 'w') as f:
    json.dump(db_records, f, indent=2)

print(f"\
Exported {len(db_records)} compounds to database import file")

Database Schema Example:

CREATE TABLE compounds (
    compound_id VARCHAR(20) PRIMARY KEY,
    common_name VARCHAR(255),
    iupac_name VARCHAR(500),
    smiles VARCHAR(1000),
    molecular_formula VARCHAR(50),
    molecular_weight DECIMAL(10,4),
    created_date TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);

Best Practices:

• ✅ Use unique compound IDs for internal tracking
• ✅ Index SMILES column for substructure searching
• ✅ Include source information for data provenance
• ✅ Validate before import to prevent duplicates

Common Issues and Solutions:

Issue: Character encoding problems

• Symptom: Special characters in IUPAC names corrupted
• Solution: Use UTF-8 encoding; escape special characters

Complete Workflow Example

From compound names to standardized database:

# Step 1: Convert single compound
python scripts/main.py --name aspirin

# Step 2: Validate SMILES
python scripts/main.py --smiles "CC(=O)Oc1ccccc1C(=O)O" --validate

# Step 3: Convert IUPAC to SMILES
python scripts/main.py --iupac "ethanol"

# Step 4: List available compounds
python scripts/main.py --list

Python API Usage:

from scripts.main import ChemicalStructureConverter
import pandas as pd

def process_compound_library(
    compound_list: list,
    output_file: str = "compound_library.csv"
) -> pd.DataFrame:
    """
    Process compound library for cheminformatics analysis.
    
    Args:
        compound_list: List of compound names
        output_file: Output CSV filename
        
    Returns:
        DataFrame with standardized compound data
    """
    converter = ChemicalStructureConverter()
    
    records = []
    not_found = []
    
    print("Processing compound library...")
    print("="*60)
    
    for compound in compound_list:
        data = converter.name_to_identifiers(compound)
        
        if data:
            records.append({
                'name': compound,
                'iupac': data['iupac'],
                'smiles': data['smiles'],
                'formula': data['formula'],
                'mw': data['mw']
            })
            print(f"✅ {compound}")
        else:
            not_found.append(compound)
            print(f"❌ {compound} - not found")
    
    print("="*60)
    
    # Create DataFrame
    df = pd.DataFrame(records)
    
    # Export to CSV
    df.to_csv(output_file, index=False)
    print(f"\
Exported {len(df)} compounds to {output_file}")
    
    if not_found:
        print(f"\
⚠️  {len(not_found)} compounds not found:")
        for comp in not_found:
            print(f"  - {comp}")
    
    return df

# Process library
library = ["aspirin", "caffeine", "glucose", "ethanol", "unknown_drug"]
df = process_compound_library(library, "my_library.csv")

print("\
Library Summary:")
print(f"Total compounds: {len(df)}")
print(f"Average MW: {df['mw'].mean():.2f} g/mol")
print(f"MW range: {df['mw'].min():.2f} - {df['mw'].max():.2f} g/mol")

Expected Output Files:

chemical_data/
├── compound_library.csv       # Standardized compound data
├── missing_compounds.txt      # List of compounds not found
├── database_import.json       # JSON format for database import
└── validation_report.txt      # SMILES validation results

Common Patterns

Pattern 1: Literature to Database Conversion

Scenario: Converting compound names from publications to SMILES for database entry.

{
  "task": "literature_to_database",
  "source": "Journal article compound list",
  "input_format": "Common names and IUPAC",
  "output_format": "SMILES for database",
  "volume": "50 compounds",
  "quality_check": "Validate all SMILES"
}

Workflow:

1. Extract compound names from publication
2. Look up each compound in converter
3. Validate generated SMILES
4. Check for missing compounds
5. Manual lookup for missing entries
6. Export to database import format
7. Review and correct any errors

Output Example:

Literature Conversion Results:
  Total compounds: 50
  Successfully converted: 47 (94%)
  Manual review needed: 3
    - Compound_23: ambiguous name
    - Compound_31: salt form unclear
    - Compound_45: stereochemistry unspecified
  
Database ready: 47 compounds exported

Pattern 2: Cheminformatics Pipeline Preparation

Scenario: Preparing compound library for virtual screening pipeline.

{
  "task": "virtual_screening_prep",
  "library_size": "10,000 compounds",
  "source_formats": ["SDF", "SMILES", "MOL"],
  "target_format": "Canonical SMILES",
  "requirements": [
    "Validate all structures",
    "Remove duplicates",
    "Calculate properties",
    "Flag reactive groups"
  ]
}

Workflow:

1. Load compound library from various sources
2. Convert all to SMILES format
3. Validate SMILES syntax
4. Remove duplicates by canonical SMILES
5. Calculate molecular properties (MW, formula)
6. Filter by drug-like properties if needed
7. Export standardized library

Output Example:

Virtual Screening Library Preparation:
  Input: 10,000 compounds
  After validation: 9,847 (153 invalid SMILES removed)
  After deduplication: 9,520 (327 duplicates removed)
  
Property Distribution:
  MW range: 150-650 Da
  Average MW: 387.5 Da
  MW < 500: 8,234 compounds (86%)
  
Ready for docking: 9,520 compounds

Pattern 3: Patent Compound Extraction

Scenario: Extracting and standardizing compounds from patent text.

{
  "task": "patent_extraction",
  "source": "US Patent with IUPAC names",
  "compounds": "25 specific compounds",
  "challenge": "Complex IUPAC names",
  "output": "SMILES for SAR analysis"
}

Workflow:

1. Extract IUPAC names from patent text
2. Parse names using converter
3. Generate SMILES for each
4. Validate structures
5. Create SAR table with consistent formatting
6. Compare with known compounds
7. Flag novel structures

Output Example:

Patent Compound Extraction:
  Patent: US10,XXX,XXX
  Compounds extracted: 25
  Successfully converted: 22 (88%)
  
Novel compounds identified: 3
  - Compound A: New scaffold
  - Compound B: Known scaffold, new substitution
  - Compound C: Prodrug of known compound
  
SAR Table Generated: 22 compounds × 5 properties

Pattern 4: Inventory Database Cleanup

Scenario: Standardizing existing chemical inventory with mixed naming.

{
  "task": "inventory_cleanup",
  "current_state": "Mixed naming conventions",
  "compounds": "500 chemicals",
  "issues": [
    "Inconsistent naming",
    "Missing SMILES",
    "Duplicate entries"
  ]
}

Workflow:

1. Export current inventory to CSV
2. Parse compound names
3. Convert all to standard format
4. Identify duplicates by SMILES
5. Merge duplicate records
6. Add missing SMILES
7. Import cleaned data back

Output Example:

Inventory Cleanup Results:
  Original entries: 500
  Unique compounds: 487 (13 duplicates removed)
  
Standardization:
  - Common names standardized: 487
  - SMILES added: 423
  - IUPAC names added: 487
  - MW calculated: 487
  
Data Quality Improvement:
  Completeness: 65% → 100%
  Consistency: 40% → 98%

Quality Checklist

Pre-Conversion:

• [ ] Verify compound names are spelled correctly
• [ ] Check for stereochemical information (R/S, E/Z)
• [ ] Note salt forms and hydrates
• [ ] Identify any ambiguous or generic names
• [ ] Prepare list of expected compounds for validation

During Conversion:

• [ ] Validate all generated SMILES
• [ ] Check stereochemistry preservation
• [ ] Verify molecular formulas match expected
• [ ] Confirm molecular weights reasonable
• [ ] Flag any compounds not found in database

Post-Conversion:

• [ ] Review all conversions for accuracy
• [ ] Manually verify random sample (5-10%)
• [ ] Check for duplicate structures
• [ ] Validate unique compound IDs
• [ ] Export in required format

Database Import:

• [ ] Test import with small subset first
• [ ] Verify foreign key constraints
• [ ] Check character encoding (UTF-8)
• [ ] Validate required fields populated
• [ ] Create backup before bulk import

Common Pitfalls

Input Data Issues:

• ❌ Ambiguous names → Multiple compounds match name

- ✅ Use CAS numbers or specific synonyms

• ❌ Mixtures and salts → Complex structures unclear

- ✅ Specify components or use main active compound

• ❌ Stereochemistry omitted → Racemic vs pure unclear

- ✅ Specify stereochemistry explicitly

• ❌ Hydrates vs anhydrous → Different molecular weights

- ✅ Always specify form in compound name

Conversion Errors:

• ❌ Invalid SMILES → Unbalanced parentheses or brackets

- ✅ Always validate SMILES after generation

• ❌ Loss of stereochemistry → Chiral centers become racemic

- ✅ Check @ symbols preserved in SMILES

• ❌ Tautomeric ambiguity → Keto/enol forms differ

- ✅ Use canonical tautomers for consistency

• ❌ Aromaticity errors → Kekulé vs aromatic forms

- ✅ Use consistent aromatic representation

Database Issues:

• ❌ Duplicate entries → Same compound multiple times

- ✅ Deduplicate by canonical SMILES

• ❌ Character encoding → Special characters corrupted

- ✅ Use UTF-8 encoding throughout

• ❌ Missing fields → Required data not populated

- ✅ Validate all required fields present

• ❌ Inconsistent formatting → Mixed naming conventions

- ✅ Apply standardization rules uniformly

Troubleshooting

Problem: Compound not found in database

• Symptoms: Returns None for valid compound name
• Causes:

- Database limited to common compounds - Name variation not recognized - Very new or obscure compound

• Solutions:

- Try alternative names or synonyms - Use external database (PubChem API) - Manually create entry for novel compounds

Problem: SMILES validation fails

• Symptoms: Valid-looking SMILES rejected
• Causes:

- Unbalanced brackets/parentheses - Invalid atom symbols - Ring closure errors

• Solutions:

- Check for typos in SMILES - Use SMILES visualization tool to debug - Generate SMILES from structure drawing

Problem: Stereochemistry lost in conversion

• Symptoms: Chiral compound becomes achiral
• Causes:

- Stereochemistry not specified in input - Conversion tool ignores stereochemistry - Wrong SMILES format used

• Solutions:

- Use isomeric SMILES with @ symbols - Check input has stereochemical info - Use tools that preserve stereochemistry

Problem: Multiple SMILES for same compound

• Symptoms: Same compound has different SMILES strings
• Causes:

- Different tautomeric forms - Different aromatic representations - Different starting atoms

• Solutions:

- Use canonical SMILES generation - Normalize tautomers - Use InChI for unique identification

Problem: Molecular weight mismatch

• Symptoms: Calculated MW differs from expected
• Causes:

- Salt form included/excluded - Isotopic composition different - Hydrate form

• Solutions:

- Specify exact compound form - Check formula calculation - Use exact mass for precision work

References

Available in references/ directory:

• (No reference files currently available for this skill)

External Resources:

• PubChem: https://pubchem.ncbi.nlm.nih.gov
• ChemSpider: http://www.chemspider.com
• SMILES Specification: http://opensmiles.org
• InChI Standard: https://www.inchi-trust.org
• RDKit Documentation: https://www.rdkit.org/docs/

Scripts

Located in scripts/ directory:

• main.py - Chemical structure conversion and validation engine

Chemical Identifier Quick Reference

SMILES Notation:

• C = aliphatic carbon
• c = aromatic carbon
• = = double bond
• # = triple bond
• () = branching
• [] = explicit valence/charge
• @ = anticlockwise (S)
• @@ = clockwise (R)

IUPAC Naming:

• Use systematic nomenclature
• Specify stereochemistry (R/S, E/Z)
• Include salt forms when relevant
• Indicate hydration state

Molecular Formula (Hill System):

• C first, then H, then alphabetical
• Example: C6H12O6 (glucose)

Parameters

Usage

Basic Usage

# Convert by compound name
python scripts/main.py --name aspirin

# Convert SMILES to IUPAC
python scripts/main.py --smiles "CC(=O)Oc1ccccc1C(=O)O"

# Validate SMILES
python scripts/main.py --smiles "CCO" --validate

# List all compounds
python scripts/main.py --list

Risk Assessment

Security Checklist

• [x] No hardcoded credentials or API keys
• [x] No file system access
• [x] Input validation for chemical identifiers
• [x] Output does not expose sensitive information
• [x] Error messages sanitized
• [x] Script execution in sandboxed environment

Prerequisites

# Python 3.7+
# No additional packages required (uses standard library)

Evaluation Criteria

Success Metrics

• [x] Successfully converts between chemical formats
• [x] Validates SMILES syntax
• [x] Retrieves compound information by name
• [x] Lists available compounds

Test Cases

1. Name Lookup: Aspirin → Returns SMILES, IUPAC, formula
2. SMILES Conversion: Valid SMILES → IUPAC name
3. Validation: Invalid SMILES → Error message

Lifecycle Status

• Current Stage: Active
• Next Review Date: 2026-03-09
• Known Issues: Limited compound database (mock data)
• Planned Improvements:

- Integrate with PubChem API - Add 2D/3D structure generation - Expand compound database

Last Updated: 2026-02-09 Skill ID: 185 Version: 2.0 (K-Dense Standard)