The targeted quantitative structure-property relationship (TQSPR) method of Brauner et a]. [2006. A structurally "targeted" QSPR method for property prediction. Industrial & Engineering Chemistry Research 45, 8430-84371 is analyzed in this study with examples involving prediction of critical temperatures of hydrocarbons. Targeted are 108 hydrocarbons, for which experimental critical temperature values can be obtained from published sources. Each hydrocarbon structure is represented by 1630 calculated values of molecular descriptors. The availability of a wide variety of molecular descriptors and small training sets comprising compounds structurally similar to the target enables the detection of one, dominant descriptor, which is well correlated with a particular property and is sufficient to serve as a single predictor for this property. The analysis of the relationship between the dominant descriptor and property values for the training set and the target compound enables better understanding of the main causes for increased prediction errors. Based on this analysis, new quantitative indicators for assessing the reliability of the predicted property value are proposed, which may reduce considerably the uncertainty associated with property prediction. (c) 2007 Elsevier Ltd. All rights reserved.