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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:cilastatin
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Accession:CHEBI:3697 term browser browse the term
Definition:The thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4.
Synonyms:exact_synonym: (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
 related_synonym: (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid;   (Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine;   (Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid;   Formula=C16H26N2O5S;   InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1;   InChIKey=DHSUYTOATWAVLW-WFVMDLQDSA-N;   SMILES=CC1(C)C[C@@H]1C(=O)N\\C(C(O)=O)=C/CCCCSC[C@H](N)C(O)=O;   cilastatina;   cilastatine;   cilastatinum
 alt_id: CHEBI:109454;   CHEBI:143261;   CHEBI:41538
 xref: Beilstein:6895069;   CAS:82009-34-5;   DrugBank:DB01597;   Drug_Central:640;   KEGG:C01675;   KEGG:D07698
 xref_mesh: MESH:D015377
 xref: PDBeChem:CIL;   PMID:3495664;   Patent:EP48025;   Patent:EP48301;   Patent:EP72014;   Reaxys:6895069;   Wikipedia:Cilastatin
 cyclic_relationship: is_conjugate_acid_of CHEBI:59512


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cilastatin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G CASP3 caspase 3 multiple interactions EXP Cilastatin inhibits the reaction [Cisplatin results in increased activity of CASP3 protein] CTD PMID:20435919 NCBI chr15:45,744,320...45,753,252
Ensembl chr15:45,742,749...45,763,773
JBrowse link
G CASP8 caspase 8 multiple interactions EXP Cilastatin inhibits the reaction [Cisplatin results in increased activity of CASP8 protein] CTD PMID:20435919 NCBI chr15:104,923,659...104,948,470
Ensembl chr15:104,923,953...104,948,470
JBrowse link
G FASLG Fas ligand multiple interactions EXP Cilastatin inhibits the reaction [Cisplatin affects the localization of FASLG protein] CTD PMID:20435919 NCBI chr 9:115,068,314...115,075,147
Ensembl chr 9:115,068,090...115,076,475
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 885
    role 865
      biological role 865
        xenobiotic 118
          cilastatin 3
Path 2
Term Annotations click to browse term
  CHEBI ontology 885
    subatomic particle 870
      composite particle 870
        hadron 870
          baryon 870
            nucleon 870
              atomic nucleus 870
                atom 870
                  main group element atom 860
                    p-block element atom 857
                      carbon group element atom 833
                        carbon atom 832
                          organic molecular entity 832
                            organic group 392
                              organic divalent group 390
                                organodiyl group 390
                                  carbonyl group 389
                                    carbonyl compound 389
                                      carboxylic acid 267
                                        amino acid 137
                                          alpha-amino acid 104
                                            L-alpha-amino acid 103
                                              serine family amino acid 48
                                                L-cysteine 27
                                                  L-cysteine derivative 27
                                                    cilastatin 3
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