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Record Information
Version4.0
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-10-23 19:06:31 UTC
HMDB IDHMDB0015437
Secondary Accession Numbers
  • HMDB15437
Metabolite Identification
Common NameSaprisartan
DescriptionSaprisartan is an AT1 receptor antagonist. It is based on medications of losartan's prototypical chemical structure. The mode of (functional) AT1 receptor antagonism has been characterized as insurmountable/noncompetitive for saprisartan. It is very likely that slow dissociation kinetics from the AT1 receptor underlie insurmountable antagonism.(10579749)
Structure
Thumb
Synonyms
ValueSource
GR-138950CChEMBL
GR-138950SAprisartanChEMBL
Saprisartan potassiumMeSH
Sapri-sartan potassiumMeSH
Chemical FormulaC25H22BrF3N4O4S
Average Molecular Weight611.431
Monoisotopic Molecular Weight610.049723164
IUPAC Name1-{[3-bromo-2-(2-trifluoromethanesulfonamidophenyl)-1-benzofuran-5-yl]methyl}-4-cyclopropyl-2-ethyl-1H-imidazole-5-carboxamide
Traditional Namesaprisartan
CAS Registry Number146623-69-0
SMILES
CCC1=NC(C2CC2)=C(N1CC1=CC2=C(OC(=C2Br)C2=CC=CC=C2NS(=O)(=O)C(F)(F)F)C=C1)C(N)=O
InChI Identifier
InChI=1S/C25H22BrF3N4O4S/c1-2-19-31-21(14-8-9-14)22(24(30)34)33(19)12-13-7-10-18-16(11-13)20(26)23(37-18)15-5-3-4-6-17(15)32-38(35,36)25(27,28)29/h3-7,10-11,14,32H,2,8-9,12H2,1H3,(H2,30,34)
InChI KeyDUEWVPTZCSAMNB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • 2-phenylbenzofuran
  • Phenylbenzofuran
  • Sulfanilide
  • 1,2,4,5-tetrasubstituted imidazole
  • Benzofuran
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Organic sulfonic acid amide
  • Benzenoid
  • Organosulfonic acid amide
  • Sulfonyl
  • Aminosulfonyl compound
  • Organosulfonic acid or derivatives
  • Imidazole
  • Organic sulfonic acid or derivatives
  • Furan
  • Heteroaromatic compound
  • Azole
  • Trihalomethane
  • Carboxamide group
  • Primary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organosulfur compound
  • Alkyl fluoride
  • Organohalogen compound
  • Organobromide
  • Organic oxygen compound
  • Organofluoride
  • Hydrocarbon derivative
  • Halomethane
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alkyl halide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP5.89ALOGPS
logP3.35ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)5.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.22 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity137.15 m³·mol⁻¹ChemAxon
Polarizability54.2 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lea-6500390000-e400299fe00d75260a2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0110957000-a72ae38c2d41a4d60cf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-e332f5eb30820cdefa1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9021500000-d8d9f1041ce1d4137815View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0730089000-195bd95c5056ce93a63fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900030000-9282f8ed9c687585fb9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-5f1e68080baaa3c60966View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01347 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01347 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01347
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54892
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound60921
PDB IDNot Available
ChEBI ID198341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
AGTR1
Uniprot ID:
P30556
Molecular weight:
41060.5
References
  1. Timmermans PB: Pharmacological properties of angiotensin II receptor antagonists. Can J Cardiol. 1999 Nov;15 Suppl F:26F-8F. [PubMed:10579749 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]