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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:54 UTC
HMDB IDHMDB15437
Secondary Accession NumbersNone
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
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 KeyInChIKey=DUEWVPTZCSAMNB-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
  • Phenylbenzofuran
  • 2-phenylbenzofuran
  • Sulfanilide
  • Benzofuran
  • 1,2,4,5-tetrasubstituted imidazole
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl bromide
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Imidazole
  • Furan
  • Cyclic alcohol
  • Azole
  • Trihalomethane
  • Primary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Halomethane
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.51e-02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity137.15 m3·mol-1ChemAxon
Polarizability54.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
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
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01347
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01347
  • Not Applicable
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
NuGOwiki LinkHMDB15437
Metagene LinkHMDB15437
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. [10579749 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]