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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:05 UTC
HMDB IDHMDB14323
Secondary Accession NumbersNone
Metabolite Identification
Common NameValsartan
DescriptionValsartan is an angiotensin-receptor blocker (ARB) that may be used to treat a variety of cardiac conditions including hypertension, diabetic nephropathy and heart failure. Valsartan lowers blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); it competes with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Valsartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of heart failure, systolic dysfunction, myocardial infarction and coronary artery disease.
Structure
Thumb
Synonyms
ValueSource
(S)-N-Valeryl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl}-valineChEBI
DiovanChEBI
N-(P-(O-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valineChEBI
N-Pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-L-valineChEBI
Chemical FormulaC24H29N5O3
Average Molecular Weight435.5188
Monoisotopic Molecular Weight435.227039819
IUPAC Name(2S)-3-methyl-2-[N-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
Traditional Namevalsartan
CAS Registry Number137862-53-4
SMILES
CCCCC(=O)N(CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1)[C@@H](C(C)C)C(O)=O
InChI Identifier
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
InChI KeyInChIKey=ACWBQPMHZXGDFX-QFIPXVFZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biphenyltetrazoles and derivatives. These are organic compounds containing a biphenyl attached to a tetrazole. A carbon atom of the biphenyl moiety is boned to a carbon or the nitrogen atom of the tetrazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTetrazoles
Direct ParentBiphenyltetrazoles and derivatives
Alternative Parents
Substituents
  • Biphenyltetrazole
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Biphenyl
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenylmethylamine
  • Benzylamine
  • Benzenoid
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Angiotensin II Receptor Antagonists
  • Antihypertensive Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point116 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.34e-02 g/LNot Available
LogP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 mg/mLALOGPS
logP3.68ALOGPS
logP5.27ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-0.11ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.07 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity134.77 m3·mol-1ChemAxon
Polarizability47.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Valsartan Action PathwaySMP00165Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00177
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00177
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00177
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54833
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValsartan
NuGOwiki LinkHMDB14323
Metagene LinkHMDB14323
METLIN IDNot Available
PubChem Compound60846
PDB IDNot Available
ChEBI ID9927
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer.
  2. Diovan. (2009). [Electronic version]. e-CPS. Retrieved December 28, 2009.
  3. Stanfield, C.L., & Germann, W.J. (2008). Principles of human physiology (3rd ed.). San Francisco, CA: Pearson Education, Inc.