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CHEBI:8803 - remikiren

ChEBI IDCHEBI:8803
ChEBI Nameremikiren
Stars
DefinitionAn L-histidine derivative that is L-histidine in which one of the amino hydrogens is replaced by a (2S)-2-[(2-methylpropane-2-sulfonyl)methyl]-3-phenylpropanoyl group and the carboxy group is replaced by a [(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino group. It is a renin inhibitor which was under development for the treatment of hypertension (now discontinued).
Last Modified23 November 2020
DownloadsMolfile
FormulaC33H50N4O6S
Net Charge0
Average Mass630.852
Monoisotopic Mass630.34511
SMILESCC(C)(C)S(=O)(=O)C[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1cncn1)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)C1CC1
InChIInChI=1S/C33H50N4O6S/c1-33(2,3)44(42,43)20-25(16-22-10-6-4-7-11-22)31(40)37-28(18-26-19-34-21-35-26)32(41)36-27(17-23-12-8-5-9-13-23)30(39)29(38)24-14-15-24/h4,6-7,10-11,19,21,23-25,27-30,38-39H,5,8-9,12-18,20H2,1-3H3,(H,34,35)(H,36,41)(H,37,40)/t25-,27+,28+,29+,30-/m1/s1
InChIKeyUXIGZRQVLGFTOU-VQXQMPIVSA-N
Wikipedia
Roles Classification
Biological Roles:
EC 3.4.23.15 (renin) inhibitor  An EC 3.4.23.* (aspartic endopeptidase) inhibitor that interferes with the activity of renin (EC 3.4.23.15).
peptidomimetic  A small protein-like chain designed to mimic a peptide.
Applications:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vasodilator agent  A drug used to cause dilation of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
remikiren (CHEBI:8803) has role antihypertensive agent (CHEBI:35674)
remikiren (CHEBI:8803) has role EC 3.4.23.15 (renin) inhibitor (CHEBI:166822)
remikiren (CHEBI:8803) has role peptidomimetic (CHEBI:63175)
remikiren (CHEBI:8803) has role vasodilator agent (CHEBI:35620)
remikiren (CHEBI:8803) is a L-histidine derivative (CHEBI:84076)
remikiren (CHEBI:8803) is a cyclopropanes (CHEBI:51454)
remikiren (CHEBI:8803) is a diol (CHEBI:23824)
remikiren (CHEBI:8803) is a secondary carboxamide (CHEBI:140325)
remikiren (CHEBI:8803) is a sulfone (CHEBI:35850)
IUPAC Name 
Nα-[(2S)-2-benzyl-3-(tert-butylsulfonyl)propanoyl]-N-[(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-L-histidinamide
INNs  Source
remikirenWHO MedNet
rémikirèneWHO MedNet
remikirenoWHO MedNet
remikirenumWHO MedNet
Synonyms  Source
Ro 42-5892KEGG COMPOUND
Ro-42-5892DrugCentral
N-[(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-Nalpha-{(2S)-2-[(2-methylpropane-2-sulfonyl)methyl]-3-phenylpropanoyl}-L-histidinamideIUPAC
Manual XrefsDatabases
C07465KEGG COMPOUND
D09038KEGG DRUG
4696DrugCentral
DB00212DrugBank
HMDB0014357HMDB
RemikirenWikipedia
REMPDBeChem
4884377ChemSpider
Registry NumbersSources
CAS:126222-34-2ChemIDplus
Citations