<p>Degree-based graph entropies quantify structural heterogeneity by transforming vertex-degree information into a probability distribution and applying Shannon entropy. We develop a unified framework for three Prodeg-type degree-power invariants, namely the Inverse Prodeg index <InlineEquation ID="IEq1"><EquationSource Format="TEX">\(IP(G)=\sum _{v\in V(G)} d_G(v)^{1/2}\)</EquationSource></InlineEquation>, the Misbalance Prodeg index <InlineEquation ID="IEq2"><EquationSource Format="TEX">\(MP(G)=\sum _{v\in V(G)} d_G(v)^{3/2}\)</EquationSource></InlineEquation>, and the Yemen Prodeg index <InlineEquation ID="IEq3"><EquationSource Format="TEX">\(YP(G)=\sum _{v\in V(G)} d_G(v)^{5/2}\)</EquationSource></InlineEquation>, together with their associated entropies <InlineEquation ID="IEq4"><EquationSource Format="TEX">\(E_{IP}(G)\)</EquationSource></InlineEquation>, <InlineEquation ID="IEq5"><EquationSource Format="TEX">\(E_{MP}(G)\)</EquationSource></InlineEquation>, and <InlineEquation ID="IEq6"><EquationSource Format="TEX">\(E_{YP}(G)\)</EquationSource></InlineEquation>. More generally, for <InlineEquation ID="IEq7"><EquationSource Format="TEX">\(a&gt;0\)</EquationSource></InlineEquation> we consider the degree-weighted distribution <InlineEquation ID="IEq8"><EquationSource Format="TEX">\(p_v\propto d_G(v)^a\)</EquationSource></InlineEquation> and the Shannon entropy <InlineEquation ID="IEq9"><EquationSource Format="TEX">\(E_a(G)\)</EquationSource></InlineEquation>, recovering the Prodeg cases at <InlineEquation ID="IEq10"><EquationSource Format="TEX">\(a\in \{\tfrac{1}{2},\tfrac{3}{2},\tfrac{5}{2}\}\)</EquationSource></InlineEquation>. We derive closed-form expressions for representative graph families (complete graphs, cycles, paths, stars, and complete bipartite graphs) and establish sharp extremal behavior: for connected graphs on <InlineEquation ID="IEq11"><EquationSource Format="TEX">\(n\ge 2\)</EquationSource></InlineEquation> vertices, <InlineEquation ID="IEq12"><EquationSource Format="TEX">\(E_{IP}(G),E_{MP}(G),E_{YP}(G)\le \log n\)</EquationSource></InlineEquation>, with equality if and only if <i>G</i> is regular, while highly imbalanced families (e.g., stars) exhibit strong concentration and vanishing entropy for <InlineEquation ID="IEq13"><EquationSource Format="TEX">\(a&gt;1\)</EquationSource></InlineEquation> as <InlineEquation ID="IEq14"><EquationSource Format="TEX">\(n\rightarrow \infty\)</EquationSource></InlineEquation>. We further provide explicit two-sided bounds in terms of degree extremes and concentration control via the heaviest weight. A main structural result is a tensor-product principle: <InlineEquation ID="IEq15"><EquationSource Format="TEX">\(S_a(G)=\sum _v d_G(v)^a\)</EquationSource></InlineEquation> is multiplicative under the tensor (Kronecker) product, implying additivity of <InlineEquation ID="IEq16"><EquationSource Format="TEX">\(E_a\)</EquationSource></InlineEquation> and the Nordhaus–Gaddum-type bound <InlineEquation ID="IEq17"><EquationSource Format="TEX">\(E_a(G)+E_a(\overline{G})\le 2\log n\)</EquationSource></InlineEquation> whenever both entropies are defined. Using majorization, we also prove a monotone exponent hierarchy <InlineEquation ID="IEq18"><EquationSource Format="TEX">\(E_{IP}(G)\ge E_{MP}(G)\ge E_{YP}(G)\)</EquationSource></InlineEquation>, with equality throughout precisely for regular graphs. To demonstrate chemical relevance, we analyze <InlineEquation ID="IEq19"><EquationSource Format="TEX">\(N=3219\)</EquationSource></InlineEquation> antibacterial compounds curated from the ChEMBL database and show that both classical degree-entropies and Prodeg entropies strongly track established molecular information/complexity measures (BertzCT and <InlineEquation ID="IEq20"><EquationSource Format="TEX">\(\log _{10}(\textrm{Ipc})\)</EquationSource></InlineEquation>), while AvgIpc exhibits weaker and nonlinear associations. Finally, we benchmark entropy-only QSPR models for nine physicochemical endpoints using 5-fold cross-validation. Tree ensembles deliver the strongest performance, with particularly high accuracy for size-related properties such as MolMR (<InlineEquation ID="IEq21"><EquationSource Format="TEX">\(R^2=0.970\)</EquationSource></InlineEquation>) and Molecular Weight (<InlineEquation ID="IEq22"><EquationSource Format="TEX">\(R^2=0.945\)</EquationSource></InlineEquation>), whereas MolLogP remains challenging (<InlineEquation ID="IEq23"><EquationSource Format="TEX">\(R^2=0.268\)</EquationSource></InlineEquation>). Across endpoints, the Prodeg block is competitive despite using fewer descriptors, and combining classical and Prodeg entropies yields consistent (typically modest) RMSE gains, supporting Prodeg entropies as compact and interpretable descriptors for chemical graph analysis and QSPR modeling.</p>

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Prodeg type Shannon graph entropies with closed forms bounds and QSPR modeling

  • Mohammed Alsharafi,
  • Yusuf Zeren

摘要

Degree-based graph entropies quantify structural heterogeneity by transforming vertex-degree information into a probability distribution and applying Shannon entropy. We develop a unified framework for three Prodeg-type degree-power invariants, namely the Inverse Prodeg index \(IP(G)=\sum _{v\in V(G)} d_G(v)^{1/2}\), the Misbalance Prodeg index \(MP(G)=\sum _{v\in V(G)} d_G(v)^{3/2}\), and the Yemen Prodeg index \(YP(G)=\sum _{v\in V(G)} d_G(v)^{5/2}\), together with their associated entropies \(E_{IP}(G)\), \(E_{MP}(G)\), and \(E_{YP}(G)\). More generally, for \(a>0\) we consider the degree-weighted distribution \(p_v\propto d_G(v)^a\) and the Shannon entropy \(E_a(G)\), recovering the Prodeg cases at \(a\in \{\tfrac{1}{2},\tfrac{3}{2},\tfrac{5}{2}\}\). We derive closed-form expressions for representative graph families (complete graphs, cycles, paths, stars, and complete bipartite graphs) and establish sharp extremal behavior: for connected graphs on \(n\ge 2\) vertices, \(E_{IP}(G),E_{MP}(G),E_{YP}(G)\le \log n\), with equality if and only if G is regular, while highly imbalanced families (e.g., stars) exhibit strong concentration and vanishing entropy for \(a>1\) as \(n\rightarrow \infty\). We further provide explicit two-sided bounds in terms of degree extremes and concentration control via the heaviest weight. A main structural result is a tensor-product principle: \(S_a(G)=\sum _v d_G(v)^a\) is multiplicative under the tensor (Kronecker) product, implying additivity of \(E_a\) and the Nordhaus–Gaddum-type bound \(E_a(G)+E_a(\overline{G})\le 2\log n\) whenever both entropies are defined. Using majorization, we also prove a monotone exponent hierarchy \(E_{IP}(G)\ge E_{MP}(G)\ge E_{YP}(G)\), with equality throughout precisely for regular graphs. To demonstrate chemical relevance, we analyze \(N=3219\) antibacterial compounds curated from the ChEMBL database and show that both classical degree-entropies and Prodeg entropies strongly track established molecular information/complexity measures (BertzCT and \(\log _{10}(\textrm{Ipc})\)), while AvgIpc exhibits weaker and nonlinear associations. Finally, we benchmark entropy-only QSPR models for nine physicochemical endpoints using 5-fold cross-validation. Tree ensembles deliver the strongest performance, with particularly high accuracy for size-related properties such as MolMR (\(R^2=0.970\)) and Molecular Weight (\(R^2=0.945\)), whereas MolLogP remains challenging (\(R^2=0.268\)). Across endpoints, the Prodeg block is competitive despite using fewer descriptors, and combining classical and Prodeg entropies yields consistent (typically modest) RMSE gains, supporting Prodeg entropies as compact and interpretable descriptors for chemical graph analysis and QSPR modeling.