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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015439
Secondary Accession Numbers
  • HMDB15439
Metabolite Identification
Common NameTasosartan
DescriptionTasosartan is only found in individuals that have used or taken this drug. It is a long-acting angiotensin II (AngII) receptor blocker. Its long duration of action has been attributed to its active metabolite enoltasosartan. It is used to treat patients with essential hypertensionTasosartan is a selective, potent, orally active and long-acting nonpeptide Angiotensin II type 1 (AT1) receptor antagonist. Tasosartan blocks the renin-angiotensin-aldosterone system (RAAS) at the level of the AT1 receptor that mediates most, if not all, of the important actions of Ang II. Tasosartan binds reversibly to the AT1 receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in decreases in systemic vascular resistance. AT1 receptor antagonists avoid the nonspecificity of the Ang I converting enzyme (ACE) inhibitors.
Structure
Data?1582753298
Synonyms
ValueSource
ANA-756tasosartanHMDB
5,8-Dihydro-2,4-dimethyl-8-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)pyrido(2,3-D)pyrimidin-7(6H)-oneHMDB
ANA-756HMDB
Taso-sartanHMDB
ANA 756HMDB
Chemical FormulaC23H21N7O
Average Molecular Weight411.4591
Monoisotopic Molecular Weight411.180758329
IUPAC Name2,4-dimethyl-8-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-7-one
Traditional Nametasosartan
CAS Registry Number145733-36-4
SMILES
CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C=C3)C3=CC=CC=C3C3=NNN=N3)C2=N1
InChI Identifier
InChI=1S/C23H21N7O/c1-14-18-11-12-21(31)30(23(18)25-15(2)24-14)13-16-7-9-17(10-8-16)19-5-3-4-6-20(19)22-26-28-29-27-22/h3-10H,11-13H2,1-2H3,(H,26,27,28,29)
InChI KeyADXGNEYLLLSOAR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Phenyltetrazole
  • Pyridopyrimidine
  • Pyridine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP3.07ALOGPS
logP4.18ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)2.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.55 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.61 m³·mol⁻¹ChemAxon
Polarizability44.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.65131661259
DarkChem[M-H]-195.40631661259
DeepCCS[M+H]+201.30230932474
DeepCCS[M-H]-198.94430932474
DeepCCS[M-2H]-232.36930932474
DeepCCS[M+Na]+207.59730932474
AllCCS[M+H]+201.932859911
AllCCS[M+H-H2O]+199.332859911
AllCCS[M+NH4]+204.332859911
AllCCS[M+Na]+205.032859911
AllCCS[M-H]-200.932859911
AllCCS[M+Na-2H]-200.832859911
AllCCS[M+HCOO]-200.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TasosartanCC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C=C3)C3=CC=CC=C3C3=NNN=N3)C2=N14746.5Standard polar33892256
TasosartanCC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C=C3)C3=CC=CC=C3C3=NNN=N3)C2=N13991.6Standard non polar33892256
TasosartanCC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C=C3)C3=CC=CC=C3C3=NNN=N3)C2=N14145.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tasosartan,1TMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C)N=N4)C=C3)C2=N14173.5Semi standard non polar33892256
Tasosartan,1TMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C)N=N4)C=C3)C2=N13927.4Standard non polar33892256
Tasosartan,1TMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C)N=N4)C=C3)C2=N15358.3Standard polar33892256
Tasosartan,1TBDMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C(C)(C)C)N=N4)C=C3)C2=N14309.8Semi standard non polar33892256
Tasosartan,1TBDMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C(C)(C)C)N=N4)C=C3)C2=N14144.5Standard non polar33892256
Tasosartan,1TBDMS,isomer #1CC1=NC(C)=C2CCC(=O)N(CC3=CC=C(C4=CC=CC=C4C4=NN([Si](C)(C)C(C)(C)C)N=N4)C=C3)C2=N15285.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tasosartan GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0549000000-19495bd41ec12908ff702017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tasosartan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 10V, Positive-QTOFsplash10-03di-0131900000-f3af74bdd6629a1057262016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 20V, Positive-QTOFsplash10-03dr-0879300000-8269237632c039f12e522016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 40V, Positive-QTOFsplash10-000i-1592000000-980b45c1d09131ebdf6e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 10V, Negative-QTOFsplash10-03di-0400900000-fd81ab030f2eb998e74b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 20V, Negative-QTOFsplash10-01t9-0923500000-5cca310860df9ec45c872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 40V, Negative-QTOFsplash10-0nov-1900000000-f6721900e79fe657f4f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 10V, Positive-QTOFsplash10-03di-0000900000-f6647abdaaca45ff02082021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 20V, Positive-QTOFsplash10-0bti-0097300000-d053fab47bdde20f7cc42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 40V, Positive-QTOFsplash10-0pdi-0729000000-ea79016bd9dcefdca2df2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 10V, Negative-QTOFsplash10-03di-0000900000-71807d3326e25477a37c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 20V, Negative-QTOFsplash10-0i2c-4109300000-5ac40be4ec7700a0bb472021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tasosartan 40V, Negative-QTOFsplash10-02mi-1922000000-805b0ac35d44bed298612021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01349 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01349 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01349
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54890
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTasosartan
METLIN IDNot Available
PubChem Compound60919
PDB IDNot Available
ChEBI ID215967
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 ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Elokdah HM, Friedrichs GS, Chai SY, Harrison BL, Primeau J, Chlenov M, Crandall DL: Novel human metabolites of the angiotensin-II antagonist tasosartan and their pharmacological effects. Bioorg Med Chem Lett. 2002 Aug 5;12(15):1967-71. [PubMed:12113820 ]
  2. Unger T: Pharmacology of AT1-receptor blockers. Blood Press Suppl. 2001;(3):5-10. [PubMed:11683476 ]
  3. Maillard MP, Rossat J, Brunner HR, Burnier M: Tasosartan, enoltasosartan, and angiotensin II receptor blockade: the confounding role of protein binding. J Pharmacol Exp Ther. 2000 Nov;295(2):649-54. [PubMed:11046101 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for angiotensin II. Cooperates with MTUS1 to inhibit ERK2 activation and cell proliferation
Gene Name:
AGTR2
Uniprot ID:
P50052
Molecular weight:
41183.4
References
  1. Unger T: Pharmacology of AT1-receptor blockers. Blood Press Suppl. 2001;(3):5-10. [PubMed:11683476 ]