You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-12-07 02:44:53 UTC
Secondary Accession Numbers
  • HMDB14357
Metabolite Identification
Common NameRemikiren
DescriptionRemikiren is only found in individuals that have used or taken this drug. It is an orally active, high specificity renin inhibitor. Several in vivo experiments have shown that remikiren is specific for renin and does not decrease arterial pressure by an unrelated mechanism.
ro 42-5892HMDB
Chemical FormulaC33H50N4O6S
Average Molecular Weight630.838
Monoisotopic Molecular Weight630.345106042
IUPAC Name(2S)-2-[(2R)-2-benzyl-3-(2-methylpropane-2-sulfonyl)propanamido]-N-[(2R,3S,4R)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-3-(1H-imidazol-5-yl)propanamide
Traditional Nameremikiren
CAS Registry Number126222-34-2
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfone
  • Sulfonyl
  • 1,2-diol
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 g/LNot Available
LogP3.9Not Available
Predicted Properties
Water Solubility0.021 g/LALOGPS
pKa (Strongest Acidic)12.32ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.48 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity169.6 m³·mol⁻¹ChemAxon
Polarizability68.67 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-9010120000-5532235719ef77e254aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2194078000-687e5db1ebe38791fd42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-9384021000-37f0932c80c925c2b07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009i-9365000000-532cd7f9b1ff29abe59dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0911138000-e6c65fe0807e4101dda3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-5941464000-2f5e879824df81fea5b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00c3-4970000000-2ad3571aff018fea158aView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00212 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00212 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4575384
KEGG Compound IDC07465
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRemikiren
METLIN IDNot Available
PubChem Compound5462340
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Clozel JP, Fischli W: Discovery of remikiren as the first orally active renin inhibitor. Arzneimittelforschung. 1993 Feb;43(2A):260-2. [PubMed:8498974 ]
  2. Richter WF, Whitby BR, Chou RC: Distribution of remikiren, a potent orally active inhibitor of human renin, in laboratory animals. Xenobiotica. 1996 Mar;26(3):243-54. [PubMed:8730917 ]


General function:
Involved in aspartic-type endopeptidase activity
Specific function:
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of blood pressure and increased sodium retention by the kidney
Gene Name:
Uniprot ID:
Molecular weight:
  1. van Paassen P, Navis GJ, De Jong PE, De Zeeuw D: Pretreatment renal vascular tone predicts the effect of specific renin inhibition on natriuresis in essential hypertension. Eur J Clin Invest. 1999 Dec;29(12):1019-26. [PubMed:10583449 ]
  2. MacFadyen RJ, Jones CR, Doig JK, Birnbock H, Reid JL: Responses to an orally active renin inhibitor, remikiren (Ro 42-5892), after controlled salt depletion in humans. J Cardiovasc Pharmacol. 1995 Mar;25(3):347-53. [PubMed:7769797 ]
  3. Kiowski W, Beermann J, Rickenbacher P, Haemmerli R, Thomas M, Burkart F, Meinertz T: Angiotensinergic versus nonangiotensinergic hemodynamic effects of converting enzyme inhibition in patients with chronic heart failure. Assessment by acute renin and converting enzyme inhibition. Circulation. 1994 Dec;90(6):2748-56. [PubMed:7994817 ]
  4. Hilgers KF, Fischli W, Veelken R, Mann JF: Vascular renin in the guinea pig. Suppression by the renin inhibitor remikiren. Hypertension. 1994 Jun;23(6 Pt 2):861-4. [PubMed:8206619 ]
  5. Clozel JP, Fischli W: Comparative effects of three different potent renin inhibitors in primates. Hypertension. 1993 Jul;22(1):9-17. [PubMed:8319997 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]