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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:43:19 UTC
HMDB IDHMDB0014323
Secondary Accession Numbers
  • HMDB14323
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
Data?1582753165
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
ValsHMDB
N-Valeryl-N-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)valineHMDB
TaregHMDB
KalpressHMDB
MitenHMDB
ProvasHMDB
NisisHMDB
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 KeyACWBQPMHZXGDFX-QFIPXVFZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine 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 ParentValine and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Biphenyl
  • Phenyltetrazole
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 g/LNot Available
LogP5.8Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available202.007http://allccs.zhulab.cn/database/detail?ID=AllCCS00001280
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP10(3.68) g/LALOGPS
logP10(5.27) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-0.11ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.07 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity134.77 m³·mol⁻¹ChemAxon
Polarizability47.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.5431661259
DarkChem[M-H]-202.04231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valsartan,1TMS,#1CCCCC(=O)N(CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C1)[C@H](C(=O)O[Si](C)(C)C)C(C)C3416.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Valsartan,1TMS,#2CCCCC(=O)N(CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1)[C@H](C(=O)O)C(C)C3626.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Valsartan,1TBDMS,#1CCCCC(=O)N(CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C1)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C3613.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Valsartan,1TBDMS,#2CCCCC(=O)N(CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1)[C@H](C(=O)O)C(C)C3743.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valsartan GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3094000000-1a2b93c2e5e760118ffd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valsartan GC-MS (1 TMS) - 70eV, Positivesplash10-052u-9236700000-2f92b4642db0f6e1db762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valsartan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0122900000-e2d5ae1b4433254a8ebe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-qTof , Positive-QTOFsplash10-0a4u-1492000000-bc19c44b1bd382b3180f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-QTOF , negative-QTOFsplash10-001i-0000900000-45397dbc5403f1111d852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-QTOF , negative-QTOFsplash10-003r-0303900000-1056988fef13dc9becc82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-65d8dfbf9280fcea77fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-77a9588a3e936c9d2e282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-0udi-0009000000-160f82ad0952fc9b33502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-001i-0000900000-d7bf9d8976f47e44ab4a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-0fb9-0915000000-1f5a4e134cd8450810e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-19095db3835430e9fe162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-00e9b9924b37c4db7a8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-fb8741bb91ee87d8245e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-001i-0000900000-be5ab1c8cde8851235e32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-0fb9-0915000000-08501c181e1066f2aa0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-6cabcfa5948837eddb2e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-d0aedd0bab06b374571a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0901000000-a4572421f0a393f299a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-ITFT , negative-QTOFsplash10-0udi-0009000000-0f743f9e78dce83f24142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valsartan LC-ESI-QFT , negative-QTOFsplash10-003r-0912600000-feeef5a05d8ef569460d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 10V, Positive-QTOFsplash10-000i-1055900000-71633e9ccff4a2e3fddf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 20V, Positive-QTOFsplash10-000i-3089200000-21a5c13b314fa930073e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 40V, Positive-QTOFsplash10-052r-4293000000-5b414a2cac94b4c0bad52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 10V, Negative-QTOFsplash10-000x-0009600000-4157b99813121a9c94ea2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 20V, Negative-QTOFsplash10-0f8c-1119200000-f3f0fc40c02029f258822017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valsartan 40V, Negative-QTOFsplash10-00xu-5906000000-9ea0192d8fb20dac6ee72017-07-26Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00177 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00177 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00177
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54833
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValsartan
METLIN IDNot Available
PubChem Compound60846
PDB IDNot Available
ChEBI ID9927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .