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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 Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO Cilastatin inhibits the reaction [Vancomycin results in decreased expression of and affects the localization of ABCB1 protein]; Cilastatin results in increased expression of and affects the localization of ABCB1 protein CTD PMID:28549670 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Dpep1 dipeptidase 1 decreases activity ISO Cilastatin results in decreased activity of DPEP1 protein CTD PMID:30664745 NCBI chr19:55,973,447...55,998,830
Ensembl chr19:55,982,740...55,998,208
JBrowse link

Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19786
    role 19732
      biological role 19732
        xenobiotic 18425
          cilastatin 2
Path 2
Term Annotations click to browse term
  CHEBI ontology 19786
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19675
                    p-block element atom 19675
                      carbon group element atom 19596
                        carbon atom 19586
                          organic molecular entity 19586
                            organic group 18631
                              organic divalent group 18622
                                organodiyl group 18622
                                  carbonyl group 18537
                                    carbonyl compound 18537
                                      carboxylic acid 18215
                                        amino acid 14171
                                          alpha-amino acid 11724
                                            L-alpha-amino acid 11561
                                              serine family amino acid 2489
                                                L-cysteine 1315
                                                  L-cysteine derivative 1305
                                                    cilastatin 2
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