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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 02:55:46 UTC
Update Date2022-03-07 03:17:55 UTC
HMDB IDHMDB0062513
Secondary Accession Numbers
  • HMDB62513
Metabolite Identification
Common Nameomega-COOH-tetranor-LTE3
Descriptionomega-COOH-tetranor-LTE3, also known as prochloraz-MN, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. omega-COOH-tetranor-LTE3 is a moderately basic compound (based on its pKa). omega-COOH-tetranor-LTE3 is a potentially toxic compound. Prochloraz is an imidazole fungicide that is widely used in Europe, Australia, Asia and South America for gardening and agriculture. Screening studies have shown that prochloraz elicits multiple mechanisms of action in vitro, as it antagonizes the androgen and the oestrogen receptor, agonizes the Ah receptor and inhibits aromatase activity. Prochloraz acts in vitro as a an aromatase inhibitor, aryl hydrocarbon receptor agonist, androgen receptor antagonist, and estrogen receptor antagonist. It can be used alone or in combination with other agents in case of fungal infestation of cereals. It is frequently used in the seed dressing to prevent fungal diseases of many crops, including oilseed rape, sugar beet, vegetables, rice and coffee, as well as for the protection of citrus fruits during storage and transport.
Structure
Data?1563866322
Synonyms
ValueSource
N-Propyl-N-(2-(2,4,6-trichlorophenoxy)ethyl)-1H-imidazoleHMDB
Prochloraz-MNHMDB
Chemical FormulaC15H16Cl3N3O2
Average Molecular Weight376.665
Monoisotopic Molecular Weight375.030809892
IUPAC NameN-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-1H-imidazole-1-carboxamide
Traditional Nameprochloraz
CAS Registry Number67747-09-5
SMILES
CCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C1
InChI Identifier
InChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3
InChI KeyTVLSRXXIMLFWEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Imidazole-1-carbonyl group
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Carbonic acid derivative
  • Urea
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0091 g/lALOGPS
LogP3.78ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.78ALOGPS
logP3.62ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.99 m³·mol⁻¹ChemAxon
Polarizability35.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+178.62230932474
DeepCCS[M-H]-176.26430932474
DeepCCS[M-2H]-209.1530932474
DeepCCS[M+Na]+184.9530932474
AllCCS[M+H]+179.932859911
AllCCS[M+H-H2O]+177.132859911
AllCCS[M+NH4]+182.532859911
AllCCS[M+Na]+183.332859911
AllCCS[M-H]-178.232859911
AllCCS[M+Na-2H]-178.432859911
AllCCS[M+HCOO]-178.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
omega-COOH-tetranor-LTE3CCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C13867.1Standard polar33892256
omega-COOH-tetranor-LTE3CCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C12677.9Standard non polar33892256
omega-COOH-tetranor-LTE3CCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C12697.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - omega-COOH-tetranor-LTE3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mn-9600000000-e3f1ea44e71dcb51a1152017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - omega-COOH-tetranor-LTE3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-9313000000-56ec4bdef0bfb8b84a372014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0009000000-0ae79f14e960df4bd6a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0019000000-a4cad4c2d27e0a00f7132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0ab9-4049000000-c2057b244ebdd5ab56572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9120000000-0c81235ba823fac1cfab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9210000000-597ced463ae1e858953e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9610000000-df1ee809ffe2b4459f6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00xr-6910000000-57a6bf28f0ea23b864a32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0019000000-91b319fb1a6e7777ede52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0a4i-4069000000-225b6a986f3dc3d0587e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9120000000-46b8460a97c9653aee9a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9410000000-c93a2e4fd9bcd6127fef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00di-9600000000-9fcaab5a55a00be40df32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-00xr-4900000000-57c2c3ba2bd53bbb5dd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0009000000-5ba733f6eda35e12362a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-053r-0298000000-43f074e6f36a1234e94a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-ITFT , positive-QTOFsplash10-053r-0296000000-8970d3b3dccb40b5cd402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-QFT , positive-QTOFsplash10-0ab9-6129000000-04a16f54678b2eb848a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-QFT , positive-QTOFsplash10-0a4i-0029000000-c07acfd90f90af9bc2bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 LC-ESI-QFT , positive-QTOFsplash10-05fr-9075000000-13b15aa68191fddb18972017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 10V, Positive-QTOFsplash10-00or-5209000000-b212e72b864d55b5d6852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 20V, Positive-QTOFsplash10-014i-9402000000-0a6b387ecded9dac65fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 40V, Positive-QTOFsplash10-014l-9100000000-b04c3c6d40f7449aa7a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 10V, Negative-QTOFsplash10-00di-1409000000-c02564cc693574d2f6f52016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 20V, Negative-QTOFsplash10-0006-1906000000-dc8e3ee3cdad740a721b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-COOH-tetranor-LTE3 40V, Negative-QTOFsplash10-0296-7931000000-51212958609e711c56aa2016-08-04Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDNot Available
KEGG Compound IDC11182
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73665
PDB IDNot Available
ChEBI ID8434
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