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In this work, we focus on the estimation of Shannon entropy for a given program <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varPi $$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>\u03a0<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>. As a first step, we focus on the case wherein a Boolean formula <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varphi (X,Y)$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>\u03c6<\/mml:mi>\n                    <mml:mo>(<\/mml:mo>\n                    <mml:mi>X<\/mml:mi>\n                    <mml:mo>,<\/mml:mo>\n                    <mml:mi>Y<\/mml:mi>\n                    <mml:mo>)<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> captures the relationship between inputs <jats:italic>X<\/jats:italic> and output <jats:italic>Y<\/jats:italic> of <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varPi $$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>\u03a0<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>. Such formulas <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varphi (X,Y)$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>\u03c6<\/mml:mi>\n                    <mml:mo>(<\/mml:mo>\n                    <mml:mi>X<\/mml:mi>\n                    <mml:mo>,<\/mml:mo>\n                    <mml:mi>Y<\/mml:mi>\n                    <mml:mo>)<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> have the property that for every valuation to <jats:italic>X<\/jats:italic>, there exists exactly one valuation to <jats:italic>Y<\/jats:italic> such that <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varphi $$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>\u03c6<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> is satisfied. The existing techniques require <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\mathcal {O}(2^m)$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>O<\/mml:mi>\n                    <mml:mo>(<\/mml:mo>\n                    <mml:msup>\n                      <mml:mn>2<\/mml:mn>\n                      <mml:mi>m<\/mml:mi>\n                    <\/mml:msup>\n                    <mml:mo>)<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> model counting queries, where <jats:inline-formula><jats:alternatives><jats:tex-math>$$m = |Y|$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>m<\/mml:mi>\n                    <mml:mo>=<\/mml:mo>\n                    <mml:mo>|<\/mml:mo>\n                    <mml:mi>Y<\/mml:mi>\n                    <mml:mo>|<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>.<\/jats:p><jats:p>We propose the first efficient algorithmic technique, called <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\mathsf {EntropyEstimation}$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>EntropyEstimation<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> to estimate the Shannon entropy of <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\varphi $$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>\u03c6<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> with PAC-style guarantees, i.e., the computed estimate is guaranteed to lie within a <jats:inline-formula><jats:alternatives><jats:tex-math>$$(1\\pm \\varepsilon )$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mo>(<\/mml:mo>\n                    <mml:mn>1<\/mml:mn>\n                    <mml:mo>\u00b1<\/mml:mo>\n                    <mml:mi>\u03b5<\/mml:mi>\n                    <mml:mo>)<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>-factor of the ground truth with confidence at least <jats:inline-formula><jats:alternatives><jats:tex-math>$$1-\\delta $$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mn>1<\/mml:mn>\n                    <mml:mo>-<\/mml:mo>\n                    <mml:mi>\u03b4<\/mml:mi>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>. Furthermore, <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\mathsf {EntropyEstimation}$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mi>EntropyEstimation<\/mml:mi>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> makes only <jats:inline-formula><jats:alternatives><jats:tex-math>$$\\mathcal {O}(\\frac{min(m,n)}{\\varepsilon ^2})$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>O<\/mml:mi>\n                    <mml:mo>(<\/mml:mo>\n                    <mml:mfrac>\n                      <mml:mrow>\n                        <mml:mi>m<\/mml:mi>\n                        <mml:mi>i<\/mml:mi>\n                        <mml:mi>n<\/mml:mi>\n                        <mml:mo>(<\/mml:mo>\n                        <mml:mi>m<\/mml:mi>\n                        <mml:mo>,<\/mml:mo>\n                        <mml:mi>n<\/mml:mi>\n                        <mml:mo>)<\/mml:mo>\n                      <\/mml:mrow>\n                      <mml:msup>\n                        <mml:mi>\u03b5<\/mml:mi>\n                        <mml:mn>2<\/mml:mn>\n                      <\/mml:msup>\n                    <\/mml:mfrac>\n                    <mml:mo>)<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula> counting and sampling queries, where <jats:inline-formula><jats:alternatives><jats:tex-math>$$m = |Y|$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>m<\/mml:mi>\n                    <mml:mo>=<\/mml:mo>\n                    <mml:mo>|<\/mml:mo>\n                    <mml:mi>Y<\/mml:mi>\n                    <mml:mo>|<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>, and <jats:inline-formula><jats:alternatives><jats:tex-math>$$n = |X|$$<\/jats:tex-math><mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\">\n                  <mml:mrow>\n                    <mml:mi>n<\/mml:mi>\n                    <mml:mo>=<\/mml:mo>\n                    <mml:mo>|<\/mml:mo>\n                    <mml:mi>X<\/mml:mi>\n                    <mml:mo>|<\/mml:mo>\n                  <\/mml:mrow>\n                <\/mml:math><\/jats:alternatives><\/jats:inline-formula>, thereby achieving a significant reduction in the number of model counting queries. We demonstrate the practical efficiency of our algorithmic framework via a detailed experimental evaluation. 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