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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:16:33 UTC
Update Date2022-03-07 02:56:42 UTC
HMDB IDHMDB0040700
Secondary Accession Numbers
  • HMDB40700
Metabolite Identification
Common NameDihydroferuperine
DescriptionDihydroferuperine belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine. Dihydroferuperine has been detected, but not quantified in, herbs and spices. This could make dihydroferuperine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydroferuperine.
Structure
Data?1563863579
SynonymsNot Available
Chemical FormulaC17H23NO3
Average Molecular Weight289.3694
Monoisotopic Molecular Weight289.167793607
IUPAC Name(2E,4Z)-5-(4-hydroxy-5-methoxycyclohexa-1,5-dien-1-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Traditional Name(2E,4Z)-5-(4-hydroxy-5-methoxycyclohexa-1,5-dien-1-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
CAS Registry Number77795-17-6
SMILES
COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O
InChI Identifier
InChI=1S/C17H23NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-9,13,15,19H,2,5-6,10-12H2,1H3/b7-3-,8-4+
InChI KeyPUYWOMGLUNDEFM-KYPMKJFLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassN-acylpiperidines
Direct ParentN-acylpiperidines
Alternative Parents
Substituents
  • N-acyl-piperidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point78 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility213.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.43ALOGPS
logP0.98ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)2.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.32 m³·mol⁻¹ChemAxon
Polarizability32.36 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
DarkChem[M+H]+172.41431661259
DarkChem[M-H]-168.47731661259
DeepCCS[M+H]+174.06430932474
DeepCCS[M-H]-171.70630932474
DeepCCS[M-2H]-204.59230932474
DeepCCS[M+Na]+180.15730932474
AllCCS[M+H]+171.632859911
AllCCS[M+H-H2O]+168.232859911
AllCCS[M+NH4]+174.832859911
AllCCS[M+Na]+175.832859911
AllCCS[M-H]-173.832859911
AllCCS[M+Na-2H]-174.132859911
AllCCS[M+HCOO]-174.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydroferuperineCOC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O4259.7Standard polar33892256
DihydroferuperineCOC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O2554.8Standard non polar33892256
DihydroferuperineCOC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O2967.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroferuperine,1TMS,isomer #1COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CCC1O[Si](C)(C)C2745.2Semi standard non polar33892256
Dihydroferuperine,1TBDMS,isomer #1COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CCC1O[Si](C)(C)C(C)(C)C2985.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroferuperine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l4i-2390000000-47fcff7208568c1b569f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroferuperine GC-MS (1 TMS) - 70eV, Positivesplash10-0101-7194000000-7d086cdfeb655b8f3b882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroferuperine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroferuperine 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 - Dihydroferuperine 10V, Positive-QTOFsplash10-0006-2390000000-11a16cf77db548194d052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Positive-QTOFsplash10-000i-5940000000-d3e419efb5a33d9b09a22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Positive-QTOFsplash10-000i-9100000000-262c12b98e7542987a192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Negative-QTOFsplash10-000i-0090000000-06ec6073301dbae8a4422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Negative-QTOFsplash10-001r-5290000000-2b699288a58d25ec6f3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Negative-QTOFsplash10-001i-9200000000-0f2e4bc015d350e1d0712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Negative-QTOFsplash10-000i-0090000000-1f5244541851cecc34192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Negative-QTOFsplash10-0079-0980000000-eeadcf89baeecc08a0532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Negative-QTOFsplash10-0079-3890000000-b69a74849a0ae1b5a7b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Positive-QTOFsplash10-0006-0090000000-23ed04513d8f5d80a7a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Positive-QTOFsplash10-006x-0290000000-8bf718fc0ca406ee84932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Positive-QTOFsplash10-0f79-4960000000-4609a34e11d5d896c3682021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB020502
KNApSAcK IDC00055010
Chemspider ID35015006
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752910
PDB IDNot Available
ChEBI ID174060
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1885591
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .