{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,7]],"date-time":"2026-04-07T01:41:13Z","timestamp":1775526073635,"version":"3.50.1"},"publisher-location":"Berlin, Heidelberg","reference-count":21,"publisher":"Springer Berlin Heidelberg","isbn-type":[{"value":"9783540279679","type":"print"},{"value":"9783540318798","type":"electronic"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2005]]},"DOI":"10.1007\/11530084_13","type":"book-chapter","created":{"date-parts":[[2010,7,21]],"date-time":"2010-07-21T20:31:24Z","timestamp":1279744284000},"page":"145-157","source":"Crossref","is-referenced-by-count":13,"title":["Assigning Unique Keys to Chemical Compounds for Data Integration: Some Interesting Counter Examples"],"prefix":"10.1007","author":[{"given":"Greeshma","family":"Neglur","sequence":"first","affiliation":[]},{"given":"Robert L.","family":"Grossman","sequence":"additional","affiliation":[]},{"given":"Bing","family":"Liu","sequence":"additional","affiliation":[]}],"member":"297","reference":[{"key":"13_CR1","doi-asserted-by":"crossref","unstructured":"Weininger, D.: SMILES, a Chemical Language and Information System 1: Introduction to Methodology and Encoding Rules, Medicinal Chemistry Project, Pomona College (1988)","DOI":"10.1021\/ci00057a005"},{"key":"#cr-split#-13_CR2.1","doi-asserted-by":"crossref","unstructured":"Weininger, D., Weininger, A., Weininger, J.L.: SMILES 2: Algorithm for Generation of Unique SMILES Notation, Daylight Chemical Information Systems, Irvine, California 92714 (1989);","DOI":"10.1021\/ci00062a008"},{"key":"#cr-split#-13_CR2.2","unstructured":"Note that although the Unique SMILES implementation has been changed by the Daylight Chemical Information System, this appears to be the most recent publication describing the algorithm"},{"key":"13_CR3","unstructured":"Weininger, D.: SMILES 3: Depicting Graphical Depiction of Chemical Structures, Daylight Chemical Information Systems, New Orleans, Louisiana"},{"key":"13_CR4","unstructured":"A SMILES to graph translation can be found at: http:\/\/www.daylight.com\/daycgi\/depict"},{"key":"13_CR5","unstructured":"A SMILES to UNIQUE SMILES translation can be found at, http:\/\/cactus.nci.nih.gov\/services\/translate\/"},{"key":"13_CR6","unstructured":"More counter examples can be found at the web site, http:\/\/ncdm171.lac.uic.edu\/neglur\/USMILES\/USMILES.html"},{"key":"13_CR7","unstructured":"NCI database, retrieved from http:\/\/129.43.27.140\/ncidb2\/ on (March 2, 2005)"},{"key":"13_CR8","unstructured":"Sample adjacency list used -{1:[[\u2019C\u2019,1,6,\u20190\u2019,3],[[1,2]]], 2:[[\u2019C\u2019,2,6,\u20190\u2019,2],[[1,1],[1,3]]], 3:[[\u2019C\u2019,4,6,\u20190\u2019,0],[[1,2],[2,4],[1,11]]], 4:[[\u2019C\u2019,3,6,\u20190\u2019,1],[[2,3],[1,5]]], 5:[[\u2019C\u2019,4,6,\u20190\u2019,0],[[1,4],[1,6],[2,8]]], 6:[[\u2019C\u2019,2,6,\u20190\u2019,2],[[1,5],[1,7]]], 7:[[\u2019C\u2019,1,6,\u20190\u2019,3],[[1,6]]], 8:[[\u2019C\u2019,3,6,\u20190\u2019,1],[[2,5],[1,9]]], 9:[[\u2019C\u2019,4,6,\u20190\u2019,0],[[1,8],[1,10],[2,11]]], 10:[[\u2019C\u2019,1,6,\u20190\u2019,3],[[1,9]]], 11:[[\u2019C\u2019,3,6,\u20190\u2019,1],[[1,3],[2,9]]]}"},{"key":"13_CR9","unstructured":"CANON Algorithm (Extract from Reference [2])- (1) Set the atomic vector to initial invariants. Go to step 3. (2) Set vector to product of primes corresponding to neighbors\u2019 ranks. (3) Sort vector, maintaining stability over previous ranks. (4) Rank atomic vector. (5) If not invariant partitioning, go to step 2. (6) On first pass, save partitioning as symmetry classes. (7) If highest rank is smaller than number of nodes, break ties, go to step 2. (8)... else done"},{"key":"13_CR10","unstructured":"See http:\/\/bioweb.dataspaceweb.org\/chemicalKeys (retrieved on March 2, 2005)"},{"key":"13_CR11","unstructured":"Beyer, T., Proskurowski, A.: Symmetries in graph coding. In: Proceedings of Northwest 1976 ACM\u2013CIPS Pacific Regional Symposium, pp. 198\u2013203 (1976)"},{"issue":"1","key":"13_CR12","first-page":"57","volume":"8","author":"C.B. HM","year":"1964","unstructured":"HM, C.B., Santolini, A.: A quasi-decision algorithm for the p-equivalence of two matrices. ICC Bull.\u00a08(1), 57\u201369 (1964)","journal-title":"ICC Bull."},{"key":"13_CR13","unstructured":"IUPAC, Nomenclature of Organic Chemistry. Pergamon Press, Oxford (1979)"},{"key":"13_CR14","first-page":"133","volume":"27","author":"M.H. Klin","year":"1992","unstructured":"Klin, M.H., Lebedev, O.V., Pivina, T.S., Zefirov, N.S.: Nonisomorphic cycles of maximum length in a series of chemical graphs and the problem of application of IUPAC nomenclature rules. MATCH\u00a027, 133\u2013151 (1992)","journal-title":"MATCH"},{"key":"13_CR15","unstructured":"See http:\/\/www.iupac.org\/projects\/2000\/2000-025-1-800.html (retrieved on March 2, 2005)"},{"issue":"1","key":"13_CR16","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1021\/ci00029a011","volume":"21","author":"M. Randic","year":"1981","unstructured":"Randic, M., Brissey, G.M., Wilkins, C.L.: Computer perception of topological symmetry via canonical numbering of atoms. Journal of Chemical Information and Computer Sciences\u00a021(1), 52\u201359 (1981)","journal-title":"Journal of Chemical Information and Computer Sciences"},{"key":"13_CR17","first-page":"45","volume":"30","author":"B. McKay","year":"1981","unstructured":"McKay, B.: Practical Graph Isomorphism. Congr. Numer.\u00a030, 45\u201387 (1981)","journal-title":"Congr. Numer."},{"key":"13_CR18","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1021\/c160017a018","volume":"5","author":"H.L. Morgan","year":"1965","unstructured":"Morgan, H.L.: The Generation of a Unique Machine Description for Chemical Structures \u2013 A Technique Developed at Chemical Abstracts Service. J. Chem. Doc.\u00a05, 107\u2013113 (1965)","journal-title":"J. Chem. Doc."},{"key":"13_CR19","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1021\/ci030404l","volume":"44","author":"J. Braun","year":"2004","unstructured":"Braun, J., Gugisch, R., Kerber, A., Laue, R., Meringer, M., Rcker, C.: MOLGEN-CID, A Canonizer for Molecules and Graphs Accessible through the Internet. Journal of Chemical Information and Computer Sciences\u00a044, 542\u2013548 (2004)","journal-title":"Journal of Chemical Information and Computer Sciences"},{"key":"13_CR20","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1109\/CSB.2003.1227324","volume-title":"Proceedings of the 2003 IEEE Computer Society Bioinformatics Conference (CSB 2003)","author":"R. Grossman","year":"2003","unstructured":"Grossman, R., Hamelberg, D., Kasturi, P., Liu, B.: Experimental Studies of the Universal Chemical Key (UCK) Algorithm on the NCI Database of Chemical Compounds. In: Proceedings of the 2003 IEEE Computer Society Bioinformatics Conference (CSB 2003), pp. 244\u2013250. IEEE Computer Society, Los Alamitos (2003)"}],"container-title":["Lecture Notes in Computer Science","Data Integration in the Life Sciences"],"original-title":[],"link":[{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/11530084_13.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,11,1]],"date-time":"2021-11-01T01:02:44Z","timestamp":1635728564000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/11530084_13"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005]]},"ISBN":["9783540279679","9783540318798"],"references-count":21,"URL":"https:\/\/doi.org\/10.1007\/11530084_13","relation":{},"ISSN":["0302-9743","1611-3349"],"issn-type":[{"value":"0302-9743","type":"print"},{"value":"1611-3349","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005]]}}}