@cyanheads/pubchem-mcp-server 0.1.1

package/dist/services/pubchem/pubchem-client.js

@@ -0,0 +1,546 @@
+/**
+ * @fileoverview PubChem API client with rate limiting, retry, and response parsing.
+ * Wraps both PUG REST and PUG View APIs behind a shared rate limiter.
+ * @module services/pubchem/pubchem-client
+ */
+import { PubChemNotFoundError } from './types.js';
+// ── Rate Limiter ─────────────────────────────────────────────────────
+/** Sliding-window rate limiter. Queues requests exceeding maxPerSecond. */
+class RateLimiter {
+    timestamps = [];
+    max;
+    queue = [];
+    draining = false;
+    constructor(maxPerSecond) {
+        this.max = maxPerSecond;
+    }
+    acquire() {
+        return new Promise((resolve) => {
+            this.queue.push(resolve);
+            if (!this.draining)
+                void this.drain();
+        });
+    }
+    async drain() {
+        this.draining = true;
+        while (this.queue.length > 0) {
+            const now = Date.now();
+            const cutoff = now - 1000;
+            while (this.timestamps[0] != null && this.timestamps[0] <= cutoff) {
+                this.timestamps.shift();
+            }
+            if (this.timestamps.length < this.max) {
+                this.timestamps.push(Date.now());
+                this.queue.shift()?.();
+            }
+            else {
+                const oldest = this.timestamps[0] ?? Date.now();
+                const wait = oldest + 1000 - Date.now();
+                await new Promise((r) => setTimeout(r, Math.max(10, wait)));
+            }
+        }
+        this.draining = false;
+    }
+}
+// ── Helpers ──────────────────────────────────────────────────────────
+const sleep = (ms) => new Promise((r) => setTimeout(r, ms));
+/** PubChem returns different field names than the request parameter names for some properties */
+const PROPERTY_NAME_MAP = {
+    SMILES: 'CanonicalSMILES',
+    ConnectivitySMILES: 'IsomericSMILES',
+};
+function normalizePropertyNames(row) {
+    const result = {};
+    for (const [key, value] of Object.entries(row)) {
+        result[PROPERTY_NAME_MAP[key] ?? key] = value;
+    }
+    return result;
+}
+function parseFaultMessage(text) {
+    try {
+        const data = JSON.parse(text);
+        if (data.Fault?.Message) {
+            return `${data.Fault.Code ?? 'Error'}: ${data.Fault.Message}`;
+        }
+    }
+    catch {
+        /* not JSON */
+    }
+    return;
+}
+// ── PUG View Parsing ─────────────────────────────────────────────────
+/** Recursively search PUG View sections for a heading */
+function findSection(sections, heading) {
+    for (const section of sections) {
+        if (section.TOCHeading === heading)
+            return section;
+        if (section.Section) {
+            const found = findSection(section.Section, heading);
+            if (found)
+                return found;
+        }
+    }
+    return;
+}
+/** Extract all text strings from a PUG View section and its children */
+function extractStrings(section) {
+    const strings = [];
+    if (section.Information) {
+        for (const info of section.Information) {
+            if (info.Value.StringWithMarkup) {
+                for (const swm of info.Value.StringWithMarkup) {
+                    if (swm.String)
+                        strings.push(swm.String);
+                }
+            }
+        }
+    }
+    if (section.Section) {
+        for (const sub of section.Section) {
+            strings.push(...extractStrings(sub));
+        }
+    }
+    return strings;
+}
+/** Extract GHS info items from a PUG View section */
+function extractGHSInfo(section) {
+    const infos = [];
+    if (section.Information)
+        infos.push(...section.Information);
+    if (section.Section) {
+        for (const sub of section.Section) {
+            infos.push(...extractGHSInfo(sub));
+        }
+    }
+    return infos;
+}
+/** Parse "H225: Highly flammable..." into { code, statement } */
+function parseCodedStatement(text) {
+    const match = text.match(/^([HP]\d{3}(?:\+[HP]\d{3})*)\s*[:\-–]\s*(.+)/);
+    if (match?.[1] && match[2])
+        return { code: match[1], statement: match[2].trim() };
+    const codeOnly = text.match(/^([HP]\d{3}(?:\+[HP]\d{3})*)$/);
+    if (codeOnly?.[1])
+        return { code: codeOnly[1], statement: '' };
+    return;
+}
+/** Map PubChem pictogram markup strings to human labels */
+const PICTOGRAM_LABELS = {
+    GHS01: 'Explosive',
+    GHS02: 'Flammable',
+    GHS03: 'Oxidizer',
+    GHS04: 'Compressed Gas',
+    GHS05: 'Corrosive',
+    GHS06: 'Toxic',
+    GHS07: 'Irritant',
+    GHS08: 'Health Hazard',
+    GHS09: 'Environmental Hazard',
+};
+function parsePictogram(text) {
+    for (const [code, label] of Object.entries(PICTOGRAM_LABELS)) {
+        if (text.includes(code))
+            return label;
+    }
+    return text.replace(/.*\//, '').replace(/\..*/, '');
+}
+// ── Client ───────────────────────────────────────────────────────────
+export class PubChemClient {
+    pugBase = 'https://pubchem.ncbi.nlm.nih.gov/rest/pug';
+    viewBase = 'https://pubchem.ncbi.nlm.nih.gov/rest/pug_view';
+    rateLimiter = new RateLimiter(5);
+    // ── Core HTTP ────────────────────────────────────────────────────
+    async fetchJson(url, init) {
+        for (let attempt = 0;; attempt++) {
+            await this.rateLimiter.acquire();
+            const controller = new AbortController();
+            const timeoutId = setTimeout(() => controller.abort(), 30_000);
+            try {
+                const response = await fetch(url, { ...init, signal: controller.signal });
+                if (response.ok) {
+                    return (await response.json());
+                }
+                const text = await response.text();
+                const message = parseFaultMessage(text) ?? text.slice(0, 300);
+                if (response.status === 404) {
+                    throw new PubChemNotFoundError(message);
+                }
+                // Retry once on 5xx
+                if (response.status >= 500 && attempt < 1) {
+                    await sleep(1000 * 2 ** attempt);
+                    continue;
+                }
+                throw new Error(`PubChem HTTP ${response.status}: ${message}`);
+            }
+            catch (error) {
+                if (error instanceof PubChemNotFoundError)
+                    throw error;
+                if (error instanceof Error && error.message.startsWith('PubChem HTTP 4'))
+                    throw error;
+                // Retry once on network errors
+                if (attempt < 1) {
+                    await sleep(1000 * 2 ** attempt);
+                    continue;
+                }
+                if (error instanceof Error && error.name === 'AbortError') {
+                    throw new Error('PubChem request timed out (30s)');
+                }
+                throw error;
+            }
+            finally {
+                clearTimeout(timeoutId);
+            }
+        }
+    }
+    async fetchBinary(url) {
+        await this.rateLimiter.acquire();
+        const controller = new AbortController();
+        const timeoutId = setTimeout(() => controller.abort(), 30_000);
+        try {
+            const response = await fetch(url, { signal: controller.signal });
+            if (!response.ok) {
+                const text = await response.text();
+                const message = parseFaultMessage(text) ?? text.slice(0, 300);
+                if (response.status === 404)
+                    throw new PubChemNotFoundError(message);
+                throw new Error(`PubChem HTTP ${response.status}: ${message}`);
+            }
+            return await response.arrayBuffer();
+        }
+        finally {
+            clearTimeout(timeoutId);
+        }
+    }
+    // ── CID Resolution ──────────────────────────────────────────────
+    /** Fetch CID list, with automatic ListKey polling for async searches */
+    async fetchCids(url, init) {
+        try {
+            const data = await this.fetchJson(url, init);
+            if ('Waiting' in data)
+                return this.pollListKey(data.Waiting.ListKey);
+            return data.IdentifierList.CID;
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return [];
+            throw error;
+        }
+    }
+    /** Poll a PubChem ListKey until results are ready */
+    async pollListKey(listKey, maxAttempts = 20) {
+        const pollUrl = `${this.pugBase}/compound/listkey/${listKey}/cids/JSON`;
+        for (let attempt = 0; attempt < maxAttempts; attempt++) {
+            await sleep(1500);
+            try {
+                const data = await this.fetchJson(pollUrl);
+                if ('Waiting' in data)
+                    continue;
+                return data.IdentifierList.CID;
+            }
+            catch (error) {
+                if (error instanceof PubChemNotFoundError)
+                    return [];
+                throw error;
+            }
+        }
+        throw new Error('PubChem async search timed out after polling');
+    }
+    searchByName(name) {
+        return this.fetchCids(`${this.pugBase}/compound/name/${encodeURIComponent(name)}/cids/JSON`);
+    }
+    searchBySmiles(smiles) {
+        return this.fetchCids(`${this.pugBase}/compound/smiles/cids/JSON`, {
+            method: 'POST',
+            headers: { 'Content-Type': 'application/x-www-form-urlencoded' },
+            body: new URLSearchParams({ smiles }).toString(),
+        });
+    }
+    searchByInchiKey(inchikey) {
+        return this.fetchCids(`${this.pugBase}/compound/inchikey/${encodeURIComponent(inchikey)}/cids/JSON`);
+    }
+    searchByFormula(formula, allowOther = false) {
+        const params = allowOther ? '?AllowOtherElements=true' : '';
+        return this.fetchCids(`${this.pugBase}/compound/fastformula/${encodeURIComponent(formula)}/cids/JSON${params}`);
+    }
+    searchByStructure(mode, query, queryType, threshold) {
+        const endpoint = mode === 'similarity'
+            ? 'fastsimilarity_2d'
+            : mode === 'substructure'
+                ? 'fastsubstructure'
+                : 'fastsuperstructure';
+        const thresholdParam = mode === 'similarity' ? `?Threshold=${threshold ?? 90}` : '';
+        if (queryType === 'cid') {
+            return this.fetchCids(`${this.pugBase}/compound/${endpoint}/cid/${query}/cids/JSON${thresholdParam}`);
+        }
+        // POST for SMILES to avoid encoding issues
+        const url = `${this.pugBase}/compound/${endpoint}/smiles/cids/JSON${thresholdParam}`;
+        return this.fetchCids(url, {
+            method: 'POST',
+            headers: { 'Content-Type': 'application/x-www-form-urlencoded' },
+            body: new URLSearchParams({ smiles: query }).toString(),
+        });
+    }
+    // ── Compound Data ───────────────────────────────────────────────
+    async getProperties(cids, properties) {
+        if (cids.length === 0 || properties.length === 0)
+            return [];
+        const propsPath = properties.join(',');
+        const cidStr = cids.join(',');
+        let rows;
+        // POST for large CID lists, GET for small ones
+        if (cids.length > 50) {
+            const data = await this.fetchJson(`${this.pugBase}/compound/cid/property/${propsPath}/JSON`, {
+                method: 'POST',
+                headers: { 'Content-Type': 'application/x-www-form-urlencoded' },
+                body: new URLSearchParams({ cid: cidStr }).toString(),
+            });
+            rows = data.PropertyTable.Properties;
+        }
+        else {
+            const data = await this.fetchJson(`${this.pugBase}/compound/cid/${cidStr}/property/${propsPath}/JSON`);
+            rows = data.PropertyTable.Properties;
+        }
+        // PubChem returns different field names than the request names for some properties.
+        // Normalize so consumers see the names they requested.
+        return rows.map((row) => normalizePropertyNames(row));
+    }
+    async getSynonyms(cid) {
+        try {
+            const data = await this.fetchJson(`${this.pugBase}/compound/cid/${cid}/synonyms/JSON`);
+            return data.InformationList.Information[0]?.Synonym ?? [];
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return [];
+            throw error;
+        }
+    }
+    getImage(cid, size = 'large') {
+        const sizeParam = size === 'small' ? '?image_size=small' : '?image_size=large';
+        return this.fetchBinary(`${this.pugBase}/compound/cid/${cid}/PNG${sizeParam}`);
+    }
+    async getXrefs(cid, xrefType) {
+        try {
+            const data = await this.fetchJson(`${this.pugBase}/compound/cid/${cid}/xrefs/${xrefType}/JSON`);
+            const info = data.InformationList.Information[0];
+            if (!info)
+                return [];
+            const values = info[xrefType];
+            return Array.isArray(values) ? values : [];
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return [];
+            throw error;
+        }
+    }
+    // ── PUG View ────────────────────────────────────────────────────
+    async getDescription(cid) {
+        try {
+            const data = await this.fetchJson(`${this.viewBase}/data/compound/${cid}/JSON?heading=Record+Description`);
+            const sections = data.Record.Section;
+            if (!sections)
+                return null;
+            const descSection = findSection(sections, 'Record Description');
+            if (!descSection)
+                return null;
+            const strings = extractStrings(descSection);
+            return strings.length > 0 ? strings.join('\n\n') : null;
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return null;
+            throw error;
+        }
+    }
+    async getSafetyData(cid) {
+        try {
+            const data = await this.fetchJson(`${this.viewBase}/data/compound/${cid}/JSON?heading=Safety+and+Hazards`);
+            const sections = data.Record.Section;
+            if (!sections)
+                return null;
+            const ghsSection = findSection(sections, 'GHS Classification');
+            if (!ghsSection)
+                return null;
+            const infos = extractGHSInfo(ghsSection);
+            const result = {
+                pictograms: [],
+                hazardStatements: [],
+                precautionaryStatements: [],
+            };
+            for (const info of infos) {
+                const name = info.Name?.toLowerCase() ?? '';
+                const strings = info.Value.StringWithMarkup?.map((s) => s.String).filter(Boolean) ?? [];
+                if (name.includes('signal') && strings[0]) {
+                    result.signalWord = strings[0];
+                }
+                else if (name.includes('pictogram')) {
+                    const extras = info.Value.StringWithMarkup?.flatMap((s) => s.Markup?.map((m) => m.Extra).filter((e) => e != null) ?? []) ?? [];
+                    result.pictograms.push(...(extras.length > 0 ? extras : strings).map(parsePictogram));
+                }
+                else if (name.includes('hazard') && name.includes('statement')) {
+                    for (const s of strings) {
+                        const parsed = parseCodedStatement(s);
+                        if (parsed)
+                            result.hazardStatements.push(parsed);
+                    }
+                }
+                else if (name.includes('precautionary') && name.includes('statement')) {
+                    for (const s of strings) {
+                        const parsed = parseCodedStatement(s);
+                        if (parsed)
+                            result.precautionaryStatements.push(parsed);
+                    }
+                }
+            }
+            // Deduplicate across depositors
+            result.pictograms = [...new Set(result.pictograms)];
+            const seenH = new Set();
+            result.hazardStatements = result.hazardStatements.filter((h) => {
+                if (seenH.has(h.code))
+                    return false;
+                seenH.add(h.code);
+                return true;
+            });
+            const seenP = new Set();
+            result.precautionaryStatements = result.precautionaryStatements.filter((p) => {
+                if (seenP.has(p.code))
+                    return false;
+                seenP.add(p.code);
+                return true;
+            });
+            // Extract source from references
+            const refs = data.Record.Reference;
+            if (refs?.[0]?.SourceName) {
+                result.source = refs[0].SourceName;
+            }
+            return result.signalWord || result.pictograms.length > 0 || result.hazardStatements.length > 0
+                ? result
+                : null;
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return null;
+            throw error;
+        }
+    }
+    // ── Bioactivity ─────────────────────────────────────────────────
+    async getAssaySummary(cid) {
+        try {
+            const data = await this.fetchJson(`${this.pugBase}/compound/cid/${cid}/assaysummary/JSON`);
+            return this.parseAssayTable(data);
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return [];
+            throw error;
+        }
+    }
+    parseAssayTable(data) {
+        const columns = data.Table.Columns.Column;
+        const rows = data.Table.Row;
+        // Build column index lookup — exact match
+        const col = (name) => columns.indexOf(name);
+        // Prefix match for columns with embedded units like "Activity Value [uM]"
+        const colPrefix = (prefix) => columns.findIndex((c) => c.startsWith(prefix));
+        const aidIdx = col('AID');
+        const nameIdx = col('Assay Name');
+        const outcomeIdx = col('Activity Outcome');
+        const targetAccIdx = col('Target Accession');
+        const geneIdIdx = col('Target GeneID');
+        const actValueIdx = colPrefix('Activity Value');
+        const actNameIdx = col('Activity Name');
+        // Extract unit from column name if present, e.g. "Activity Value [uM]" → "uM"
+        const actValueUnit = actValueIdx >= 0 ? (columns[actValueIdx]?.match(/\[(.+)\]/)?.[1] ?? '') : '';
+        // Group by AID to collect multiple activity values
+        const byAid = new Map();
+        for (const row of rows) {
+            const cell = row.Cell;
+            const aid = Number(cell[aidIdx]);
+            if (!aid || Number.isNaN(aid))
+                continue;
+            if (!byAid.has(aid)) {
+                const entry = {
+                    aid,
+                    assayName: String(cell[nameIdx] ?? ''),
+                    outcome: String(cell[outcomeIdx] ?? ''),
+                    activityValues: [],
+                };
+                if (targetAccIdx >= 0 && cell[targetAccIdx])
+                    entry.targetAccession = String(cell[targetAccIdx]);
+                if (geneIdIdx >= 0 && cell[geneIdIdx] != null) {
+                    const gid = Number(cell[geneIdIdx]);
+                    if (!Number.isNaN(gid) && gid > 0)
+                        entry.targetGeneId = gid;
+                }
+                byAid.set(aid, entry);
+            }
+            // Collect activity value if present
+            if (actValueIdx >= 0 && cell[actValueIdx] != null) {
+                const value = Number(cell[actValueIdx]);
+                if (!Number.isNaN(value)) {
+                    byAid.get(aid)?.activityValues.push({
+                        name: actNameIdx >= 0 ? String(cell[actNameIdx] ?? '') : '',
+                        value,
+                        unit: actValueUnit,
+                    });
+                }
+            }
+        }
+        return [...byAid.values()];
+    }
+    // ── Assay Search ────────────────────────────────────────────────
+    async searchAssaysByTarget(targetType, query) {
+        // PubChem API expects "accession" not "proteinaccession"
+        const apiTargetType = targetType === 'proteinaccession' ? 'accession' : targetType;
+        try {
+            const data = await this.fetchJson(`${this.pugBase}/assay/target/${apiTargetType}/${encodeURIComponent(query)}/aids/JSON`);
+            return data.IdentifierList.AID;
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return [];
+            throw error;
+        }
+    }
+    // ── Entity Summaries ────────────────────────────────────────────
+    async getEntitySummary(entityType, identifier) {
+        const pathMap = {
+            assay: `/assay/aid/${identifier}/summary/JSON`,
+            gene: `/gene/geneid/${identifier}/summary/JSON`,
+            protein: `/protein/accession/${encodeURIComponent(String(identifier))}/summary/JSON`,
+            taxonomy: `/taxonomy/taxid/${identifier}/summary/JSON`,
+        };
+        const path = pathMap[entityType];
+        if (!path)
+            throw new Error(`Unknown entity type: ${entityType}`);
+        try {
+            const data = await this.fetchJson(`${this.pugBase}${path}`);
+            // Response shape: { XxxSummaries: { XxxSummary: [{...}] } }
+            const summariesKey = Object.keys(data).find((k) => k.endsWith('Summaries'));
+            if (!summariesKey)
+                return null;
+            const summaries = data[summariesKey];
+            const summaryKey = Object.keys(summaries).find((k) => k.endsWith('Summary'));
+            if (!summaryKey)
+                return null;
+            const arr = summaries[summaryKey];
+            return arr[0] ?? null;
+        }
+        catch (error) {
+            if (error instanceof PubChemNotFoundError)
+                return null;
+            throw error;
+        }
+    }
+}
+// ── Init/Accessor ────────────────────────────────────────────────────
+let _client;
+export function initPubChemClient() {
+    _client = new PubChemClient();
+}
+export function getPubChemClient() {
+    if (!_client)
+        throw new Error('PubChemClient not initialized — call initPubChemClient() in setup()');
+    return _client;
+}
+//# sourceMappingURL=pubchem-client.js.map

package/dist/services/pubchem/pubchem-client.js.map

@@ -0,0 +1 @@
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