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
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:14 UTC
HMDB IDHMDB14357
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
ValueSource
ro 42-5892HMDB
(S)-alpha-((S)-alpha-((t-Butylsulfonyl)methyl)hydrocinnamamido)-N-((1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl)imidazole-4-propionamideMeSH
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
SMILES
CC(C)(C)S(=O)(=O)C[C@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC1CCCCC1)[C@H](O)[C@H](O)C1CC1
InChI Identifier
InChI=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-/m0/s1
InChI KeyInChIKey=UXIGZRQVLGFTOU-PUNKFERVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antihypertensive Agents
  • Protease Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.13e-02 g/LNot Available
LogP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 mg/mLALOGPS
logP2.42ALOGPS
logP2.37ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.32ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.48 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity169.6 m3·mol-1ChemAxon
Polarizability68.67 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00212
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00212
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00212
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4575384
KEGG Compound IDC07465
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRemikiren
NuGOwiki LinkHMDB14357
Metagene LinkHMDB14357
METLIN IDNot Available
PubChem Compound5462340
PDB IDNot Available
ChEBI IDNot Available
References
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. [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. [8730917 ]

Enzymes

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:
REN
Uniprot ID:
P00797
Molecular weight:
45057.1
References
  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. [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. [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. [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. [8206619 ]
  5. Clozel JP, Fischli W: Comparative effects of three different potent renin inhibitors in primates. Hypertension. 1993 Jul;22(1):9-17. [8319997 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]