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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 04:05:50 UTC
Update Date2021-09-26 23:00:33 UTC
HMDB IDHMDB0249581
Secondary Accession NumbersNone
Metabolite Identification
Common NameCandesartan cilexetil
Description1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylate, also known as atacand, 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. Based on a literature review very few articles have been published on 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Candesartan cilexetil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Candesartan cilexetil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
AtacandKegg
1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylic acidGenerator
1-Cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acidGenerator
KenzenMeSH
ParapresMeSH
AmiasMeSH
1-(Cyclohexylocarbonyloxy)ethyl-2-ethoxy-1-(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)-1H-benzimidazole-7-carboxylateMeSH
BlopressMeSH
TCV 116MeSH
TCV-116MeSH
Candesartan cilexetilMeSH
Chemical FormulaC33H34N6O6
Average Molecular Weight610.671
Monoisotopic Molecular Weight610.253982839
IUPAC Name1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylate
Traditional Name1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-3-{[2'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1,3-benzodiazole-4-carboxylate
CAS Registry NumberNot Available
SMILES
CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
InChI Identifier
InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
InChI KeyGHOSNRCGJFBJIB-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
  • Benzimidazole
  • Alkyl aryl ether
  • Carbonic acid diester
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Tetrazole
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Acetal
  • Carboxylic acid derivative
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.81ALOGPS
logP8.17ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)8.3ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area143.34 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity177.42 m³·mol⁻¹ChemAxon
Polarizability65.11 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+231.55430932474
DeepCCS[M-H]-229.15930932474
DeepCCS[M-2H]-262.27630932474
DeepCCS[M+Na]+237.46730932474
AllCCS[M+H]+243.132859911
AllCCS[M+H-H2O]+242.032859911
AllCCS[M+NH4]+244.132859911
AllCCS[M+Na]+244.432859911
AllCCS[M-H]-226.032859911
AllCCS[M+Na-2H]-228.032859911
AllCCS[M+HCOO]-230.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Candesartan cilexetilCCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N15596.6Standard polar33892256
Candesartan cilexetilCCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N14478.6Standard non polar33892256
Candesartan cilexetilCCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N15006.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Candesartan cilexetil,1TMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C14936.8Semi standard non polar33892256
Candesartan cilexetil,1TMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C14297.5Standard non polar33892256
Candesartan cilexetil,1TMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C16631.5Standard polar33892256
Candesartan cilexetil,1TBDMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C15019.2Semi standard non polar33892256
Candesartan cilexetil,1TBDMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14453.7Standard non polar33892256
Candesartan cilexetil,1TBDMS,isomer #1CCOC1=NC2=CC=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=C2N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C16565.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 10V, Positive-QTOFsplash10-00ed-3610901000-cfe87b96a35a5c26f3c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 20V, Positive-QTOFsplash10-006t-6924620000-621f5704d98f0be817e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 40V, Positive-QTOFsplash10-000i-9261200000-6b99a7138733c8b5962f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 10V, Negative-QTOFsplash10-066r-2603903000-c8d42f24c9dac6d016762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 20V, Negative-QTOFsplash10-004j-4901210000-17c454d474941c53f9bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 40V, Negative-QTOFsplash10-01ot-5921000000-b383ba0a7de2401e65e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 10V, Positive-QTOFsplash10-00xr-1000911000-0ed90c65d09138ebb9cb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 20V, Positive-QTOFsplash10-00yr-4132931000-3b613eff13e1097f61aa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 40V, Positive-QTOFsplash10-001i-9041210000-94578d2040a0f9fc0f512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 10V, Negative-QTOFsplash10-0a4i-0201519000-d0ac62542d19c839645b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 20V, Negative-QTOFsplash10-052k-9102602000-219b657d4746cdd49e5a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Candesartan cilexetil 40V, Negative-QTOFsplash10-054k-4092011000-badc2ac8068da5d1a0942021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2444
KEGG Compound IDC07709
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]