830:, which are not searchable for chemical content. The full InChI turned out to be too lengthy for easy searching, and therefore the InChIKey was developed. There is a very small, but nonzero chance of two different molecules having the same InChIKey, but the probability for duplication of only the first 14 characters has been estimated as only one duplication in 75 databases each containing one billion unique structures. With all databases currently having below 50 million structures, such duplication appears unlikely at present. A recent study more extensively studies the collision rate finding that the experimental collision rate is in agreement with the theoretical expectations.
330:
protons. Different input structures may give the same result; for example, acetic acid and acetate would both give the same core parent structure, that of acetic acid. A core parent structure may be disconnected, consisting of more than one component, in which case the sublayers in the InChI usually consist of sublayers for each component, separated by semicolons (periods for the chemical formula sublayer). One way this can happen is that all metal atoms are disconnected during normalization; so, for example, the InChI for tetraethyllead will have five components, one for lead and four for the ethyl groups.
112:
275:, and electronic charge information. Not all layers have to be provided; for instance, the tautomer layer can be omitted if that type of information is not relevant to the particular application. The InChI algorithm converts input structural information into a unique InChI identifier in a three-step process: normalization (to remove redundant information), canonicalization (to generate a unique number label for each atom), and serialization (to give a string of characters).
890:
458:, which is a fully standardized InChI flavor maintaining the same level of attention to structure details and the same conventions for drawing perception. The remaining information is structured as a sequence of layers and sub-layers, with each layer providing one specific type of information. The layers and sub-layers are separated by the delimiter "
756:
472:(no prefix). This is the only sublayer that must occur in every InChI. Numbers used throughout the InChI are given in the formula's element order excluding hydrogen atoms. For example, "/C10H16N5O13P3" implies that atoms numbered 1–10 are carbons, 11–15 are nitrogens, 16–28 are oxygens, and 29–31 are phosphorus.
282:
in three respects: firstly, they are freely usable and non-proprietary; secondly, they can be computed from structural information and do not have to be assigned by some organization; and thirdly, most of the information in an InChI is human readable (with practice). InChIs can thus be seen as akin
396:
can be appended, which may contain various additional sublayers; this cannot be done in standard InChI though, so different tautomers will have the same standard InChI (for example, alanine will give the same standard InChI whether input in a neutral or a zwitterionic form.) Finally, a nonstandard
303:
In
January 2009 the 1.02 version of the InChI software was released. This provided a means to generate so called standard InChI, which does not allow for user selectable options in dealing with the stereochemistry and tautomeric layers of the InChI string. The standard InChIKey is then the hashed
299:
The InChIKey, sometimes referred to as a hashed InChI, is a fixed length (27 character) condensed digital representation of the InChI that is not human-understandable. The InChIKey specification was released in
September 2007 in order to facilitate web searches for chemical compounds, since these
329:
In order to avoid generating different InChIs for tautomeric structures, before generating the InChI, an input chemical structure is normalized to reduce it to its so-called core parent structure. This may involve changing bond orders, rearranging formal charges and possibly adding and removing
645:
916:
As the InChI cannot be reconstructed from the InChIKey, an InChIKey always needs to be linked to the original InChI to get back to the original structure. InChI Resolvers act as a lookup service to make these links, and prototype services are available from
291:
notation and, in contrast to SMILES strings, every structure has a unique InChI string, which is important in database applications. Information about the 3-dimensional coordinates of atoms is not represented in InChI; for this purpose a format such as
479:"). The atoms in the chemical formula (except for hydrogens) are numbered in sequence; this sublayer describes which atoms are connected by bonds to which other ones. The type of those bonds is later specified in the stereochemical layer prefixed by "
945:
The format was originally called IChI (IUPAC Chemical
Identifier), then renamed in July 2004 to INChI (IUPAC-NIST Chemical Identifier), and renamed again in November 2004 to InChI (IUPAC International Chemical Identifier), a trademark of IUPAC.
304:
version of the standard InChI string. The standard InChI will simplify comparison of InChI strings and keys generated by different groups, and subsequently accessed via diverse sources such as databases and web resources.
954:
Scientific direction of the InChI standard is carried out by the IUPAC Division VIII Subcommittee, and funding of subgroups investigating and defining the expansion of the standard is carried out by both
284:
841:
sublayer of the charge layer) of the InChI. The second part consists of 10 characters resulting from a hash of the remaining layers of the InChI, a single character indicating the kind of InChIKey (
349:
portion of the charge layer tells how many protons (hydrogen ions) must be added to or removed from it to regenerate the original structure. If present, the stereochemical layer, with sublayers
751:{\displaystyle {\ce {\mathsf {H-{\overset {\displaystyle H \atop |}{\underset {| \atop \displaystyle H}{C}}}-{\overset {\displaystyle H \atop |}{\underset {| \atop \displaystyle H}{C}}}-O-H}}}}
1254:
1197:. However, the adoption is not straightforward, and many databases show a discrepancy between the chemical structures and the InChI they contain, which is a problem for linking databases.
244:, designed to provide a standard way to encode molecular information and to facilitate the search for such information in databases and on the web. Initially developed by the
300:
were problematic with the full-length InChI. Unlike the InChI, the InChIKey is not unique: though collisions are expected to be extremely rare, there are known collisions.
2050:
245:
249:
252:(NIST) from 2000 to 2005, the format and algorithms are non-proprietary. Since May 2009, it has been developed by the InChI Trust, a nonprofit charity from the
1211:
288:
462:" and start with a characteristic prefix letter (except for the chemical formula sub-layer of the main layer). The six layers with important sublayers are:
2025:
is a free JavaScript based molecular editor that generates InChI and InChI Key in a web browser, which allows for easy web searches of chemical compounds
401:
layer can be added, which effectively gives a new InChI generated without breaking bonds to metal atoms. This may contain various sublayers, including
902:
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
333:
The first, main, layer of the InChI refers to this core parent structure, giving its chemical formula, non-hydrogen connectivity without bond order (
1262:
2043:
991:
The InChI Trust has developed software to generate the InChI, InChIKey and other identifiers. The release history of this software follows.
311:, of which IUPAC is a member. Version 1.06 and was released in December 2020. Prior to 1.04, the software was freely available under the
778:
1981:
1041:
926:
228:
2036:
1987:
963:. The InChI Trust funds the development, testing and documentation of the InChI. Current extensions are being defined to handle
1978:
293:
321:
The current software version is 1.07.1 (August 2024), uses the MIT license, and may be downloaded from the InChI GitHub site.
2202:
2192:
1952:
1237:
uses JNI-InChI to generate InChIs, can convert InChIs into structures, and generate tautomers based on the InChI algorithms
1444:
833:
The InChIKey currently consists of three parts separated by hyphens, of 14, 10 and one character(s), respectively, like
91:
827:
603:") for tautomeric hydrogens; contains some or all of the above types of layers except atom connections; may end with "
65:
1984:
that allows generation of InChI and conversion of InChI to structure (also SMILES and generation of other properties)
1474:
1234:
918:
1206:
1186:
1941:
614:"); contains the whole InChI of a structure with reconnected metal atoms; never included in standard InChI
2018:
837:. The first 14 characters result from a SHA-256 hash of the connectivity information (the main layer and
2212:
1946:
1494:
Goodman, Jonathan M.; Pletnev, Igor; Thiessen, Paul; Bolton, Evan; Heller, Stephen R. (December 2021).
2207:
2135:
1841:
434:
2140:
1222:
312:
279:
2197:
2095:
1865:
1606:
Heller, Stephen R.; McNaught, Alan; Pletnev, Igor; Stein, Stephen; Tchekhovskoi, Dmitrii (2015).
619:
241:
138:
1994:, implementation to draw structures (or open other file formats) and output to InChI file format
307:
The continuing development of the standard has been supported since 2010 by the not-for-profit
2108:
2085:
2080:
1916:
1857:
1802:
1690:
1639:
1546:
1527:
1423:
1316:
976:
972:
498:
127:
1754:
389:) gives isotopic information. These are the only layers which can occur in a standard InChI.
2113:
2065:
1906:
1896:
1885:"Consistency of systematic chemical identifiers within and between small-molecule databases"
1849:
1792:
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1670:
1629:
1619:
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1507:
1413:
1403:
1306:
1296:
469:
205:
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122:
2000:
implements its own InChI parser and uses the IUPAC implementation to generate InChI strings
2161:
2127:
2103:
2022:
1577:
1217:
272:
318:
license,. Versions 1.05 and 1.06 used a custom license called IUPAC-InChI Trust
License.
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1334:
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1634:
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1311:
1284:
980:
520:
253:
1657:
Pletnev, I.; Erin, A.; McNaught, A.; Blinov, K.; Tchekhovskoi, D.; Heller, S. (2012).
1578:"IUPAC/InChI-Trust Licence for the International Chemical Identifier (InChI) Software"
983:, and once accepted by the Division VIII Subcommittee will be added to the algorithm.
2186:
811:
785:
1869:
1732:
2145:
1964:
889:
849:
for nonstandard), and a character indicating the version of InChI used (currently
1708:
1958:
960:
854:
1769:
Grethe, Guenter; Blanke, Gerd; Kraut, Hans; Goodman, Jonathan M. (9 May 2018).
1512:
818:
algorithm), designed to allow for easy web searches of chemical compounds. The
493:"). Describes how many hydrogen atoms are connected to each of the other atoms.
1974:
1853:
1787:
1735:
1624:
1408:
1190:
1178:
934:
777:
419:
237:
36:
1452:
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Heller, S.R.; McNaught, A.; Pletnev, I.; Stein, S.; Tchekhovskoi, D. (2015).
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131:
1920:
1901:
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1643:
1531:
1427:
1320:
1283:
Heller, S.; McNaught, A.; Stein, S.; Tchekhovskoi, D.; Pletnev, I. (2013).
1177:
The InChI has been adopted by many larger and smaller databases, including
900:
has the structure shown on the right. The standard InChI for morphine is
618:
The delimiter-prefix format has the advantage that a user can easily use a
2028:
1961:
Generates and resolves InChI/InChIKeys and many other chemical identifiers
1301:
826:. Most chemical structures on the Web up to 2007 have been represented as
1997:
1991:
1819:
897:
794:
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
527:
486:
264:
1955:
InChI final version 1.02 and explanation of
Standard InChI, January 2009
1194:
968:
964:
930:
853:
for version 1). Finally, the single character at the end indicates the
815:
760:
561:
392:
If the user wants to specify an exact tautomer, a fixed hydrogen layer
268:
100:
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1968:
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1182:
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17:
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generates InChI and InChIKeys for drawn structures or opened files
956:
888:
776:
143:
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2003:
315:
2032:
937:
has had a resolver until July 2015 when it was decommissioned.
178:
2015:
2012:
implements an InChI and InChI Key search of spectral libraries
2006:
implements an InChI and InChI Key search of spectral libraries
1936:
1285:"InChI - the worldwide chemical structure identifier standard"
622:
search to find identifiers that match only in certain layers.
263:
of information — the atoms and their bond connectivity,
220:
2009:
217:
450:. If the InChI is standard, this is followed by the letter
365:, gives stereochemical information, and the isotopic layer
1771:"International chemical identifier for reactions (RInChI)"
259:
The identifiers describe chemical substances in terms of
211:
1659:"InChIKey collision resistance: An experimental testing"
723:
705:
685:
667:
256:
which works to implement and promote the use of InChI.
1832:
Warr, W.A. (2015). "Many InChIs and quite some feat".
1255:"IUPAC International Chemical Identifier Project Page"
345:
portion of the charge layer gives its charge, and the
1445:"The IUPAC International Chemical Identifier (InChI)"
717:
709:
679:
671:
648:
287:. They can express more information than the simpler
229:
214:
1608:"InChI, the IUPAC International Chemical Identifier"
1392:"InChI, the IUPAC International Chemical Identifier"
2154:
2126:
2094:
2073:
2064:
1547:"The IUPAC International Chemical Identifier:InChl"
1496:"InChI version 1.06: now more than 99.99% reliable"
1135:IUPAC/InChI Trust InChI Licence 1.0, and BSD-style
857:of the core parent structure, corresponding to the
430:
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90:
64:
45:
35:
750:
1883:Akhondi, S. A.; Kors, J. A.; Muresan, S. (2012).
283:to a general and extremely formalized version of
246:International Union of Pure and Applied Chemistry
1601:
1599:
1597:
1439:
1437:
552:type of stereochemistry information (prefix: "
250:National Institute of Standards and Technology
2044:
1942:Description of the canonicalization algorithm
1764:
1762:
8:
1475:"InChIKey collision: the DIY copy/pastables"
1212:Simplified molecular-input line-entry system
607:" sublayer; never included in standard InChI
446:" followed by the version number, currently
413:
30:
1385:
1383:
1381:
1379:
1377:
2070:
2051:
2037:
2029:
1834:Journal of Computer-Aided Molecular Design
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904:and the standard InChIKey for morphine is
110:
29:
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537:tetrahedral stereochemistry of atoms and
993:
624:
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1473:E.L. Willighagen (17 September 2011).
739:
731:
693:
655:
412:
1959:NCI/CADD Chemical Identifier Resolver
1124:Experimental large molecule support.
873:, ... if protons should be added and
814:version of the full InChI (using the
337:sublayer) and hydrogen connectivity (
7:
1149:IUPAC/InChI Trust InChI Licence 1.0
1117:IUPAC/InChI Trust InChI Licence 1.0
1099:IUPAC/InChI Trust InChI Licence 1.0
442:Every InChI starts with the string "
1120:Support for elements 113-118 added.
1104:Support for elements 105-112 added.
278:InChIs differ from the widely used
1451:. 5 September 2007. Archived from
881:, ... if they should be removed.)
716:
703:
678:
665:
27:Identifier for chemical substances
25:
927:European Bioinformatics Institute
770:InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
193:International Chemical Identifier
204:
1081:InChI v. 1.03 source code docs
71:1.07.1 / August 9, 2024
1965:PubChem online molecule editor
861:sublayer of the charge layer (
594:" for isotopic stereochemistry
1:
1709:"Technical FAQ - InChI Trust"
1122:Experimental polymer support.
1047:Adds InChIKey functionality.
822:is the hashed counterpart of
369:(which may contain sublayers
1755:InChI Resolver, 27 July 2015
1733:"InChI=1/C17H19NO3/c1-18..."
1553:. Vol. 28, no. 6.
1061:Changed format for InChIKey.
806:The condensed, 27 character
610:Reconnected layer (prefix: "
466:Main layer (always present)
1820:Downloads of InChI Software
1360:"The InChI Trust and IUPAC"
1063:Introduces standard InChI.
906:BQJCRHHNABKAKU-KBQPJGBKSA-N
835:XXXXXXXXXXXXXX-YYYYYYYYFV-P
568:"), may include sublayers:
475:Atom connections (prefix: "
2229:
1949:a presentation to the W3C.
1889:Journal of Cheminformatics
1775:Journal of Cheminformatics
1663:Journal of Cheminformatics
1612:Journal of Cheminformatics
1513:10.1186/s13321-021-00517-z
1500:Journal of Cheminformatics
1396:Journal of Cheminformatics
1289:Journal of Cheminformatics
1138:Computes reaction InChIs.
511:proton sublayer (prefix: "
504:charge sublayer (prefix: "
1854:10.1007/s10822-015-9854-3
1788:10.1186/s13321-018-0277-8
1625:10.1186/s13321-015-0068-4
1583:. IUPAC/InChI-Trust. 2020
1409:10.1186/s13321-015-0068-4
1335:"What on Earth is InChI?"
1235:Chemistry Development Kit
1152:Revised polymer support.
919:National Cancer Institute
86:
60:
1975:ChemSpider Compound APIs
1822:, accessed Jan. 8, 2021.
1207:Molecular Query Language
1187:Golm Metabolome Database
599:Fixed-H layer (prefix: "
420:Internet media type
49:April 15, 2005
2074:Non-structural formulas
2059:Molecular visualization
1551:Chemistry International
1545:McNaught, Alan (2006).
575:" for isotopic hydrogen
1902:10.1186/1758-2946-4-35
1676:10.1186/1758-2946-4-39
950:Continuing development
894:
789:
752:
2203:Chemical file formats
2193:Chemical nomenclature
1302:10.1186/1758-2946-5-7
1166:Code moved to GitHub
1106:CML support removed.
997:Software and version
892:
780:
753:
73:; 38 days ago
2136:Ball-and-stick model
1242:Notes and references
865:for no protonation,
646:
435:chemical file format
280:CAS registry numbers
2141:Space-filling model
2096:Structural formulas
1947:Googling for InChIs
1846:2015JCAMD..29..681W
1455:on October 30, 2007
1223:SYBYL Line Notation
627:
415:
242:chemical substances
32:
2021:2015-01-06 at the
1953:InChI Release 1.02
1035:InChI v. 1.02beta
973:Markush structures
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893:Morphine structure
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2109:Condensed formula
2086:Molecular formula
2081:Empirical formula
2066:Chemical formulas
1971:/SMARTS and InChI
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845:for standard and
820:standard InChIKey
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409:Format and layers
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128:Microsoft Windows
16:(Redirected from
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2128:Molecular models
2114:Skeletal formula
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1937:IUPAC InChI site
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1261:. Archived from
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1157:InChI v. 1.07.1
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1129:RInChI v. 1.00
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981:organometallics
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923:UniChem service
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912:InChI resolvers
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1263:the original
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1163:MIT License
1102:New license.
1026:August 2006
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181:.inchi-trust
154:Available in
105:/IUPAC-InChI
37:Developer(s)
2208:Identifiers
2010:SpectraBase
1977:ChemSpider
1132:March 2017
1084:March 2011
1014:April 2005
1011:InChI v. 1
961:InChI Trust
855:protonation
578:sublayers "
313:open-source
309:InChI Trust
285:IUPAC names
169:MIT License
41:InChI Trust
2187:Categories
2155:Other ways
1741:2007-09-18
1736:Chemspider
1718:2021-01-08
1587:2022-08-09
1560:2007-09-18
1480:2012-11-06
1459:2007-09-18
1366:August 22,
1269:2012-12-05
1191:OpenPHACTS
1179:ChemSpider
1160:Aug. 2024
1146:Dec. 2020
1114:Jan. 2017
1096:Sep. 2011
1071:June 2010
1055:Jan. 2009
1038:Sep. 2007
935:ChemSpider
788:with InChI
571:sublayer "
530:(prefix: "
325:Generation
265:tautomeric
238:identifier
201:pronounced
92:Repository
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53:2005-04-15
2198:Encodings
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1339:IUPAC 100
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1074:LGPL 2.1
1058:LGPL 2.1
1006:Comments
977:reactions
828:GIF files
740:−
732:−
694:−
656:−
626:Examples
528:cumulenes
132:Unix-like
2019:Archived
1992:ChemAxon
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1862:26081259
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