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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:15:51 UTC
Update Date2022-03-07 02:53:45 UTC
HMDB IDHMDB0033526
Secondary Accession Numbers
  • HMDB33526
Metabolite Identification
Common NameChalciporone
DescriptionChalciporone belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Chalciporone has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make chalciporone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chalciporone.
Structure
Data?1563862419
Synonyms
ValueSource
2-Methyl-7-(7-oxo-1,3-nonadienyl)-2H-azepineHMDB
Chemical FormulaC16H21NO
Average Molecular Weight243.344
Monoisotopic Molecular Weight243.162314299
IUPAC Name(6E,8Z)-9-(7-methyl-3H-azepin-2-yl)nona-6,8-dien-3-one
Traditional Name(6E,8Z)-9-(7-methyl-3H-azepin-2-yl)nona-6,8-dien-3-one
CAS Registry Number112448-74-5
SMILES
CCC(=O)CC\C=C\C=C/C1=NC(C)=CC=CC1
InChI Identifier
InChI=1S/C16H21NO/c1-3-16(18)13-7-5-4-6-11-15-12-9-8-10-14(2)17-15/h4-6,8-11H,3,7,12-13H2,1-2H3/b5-4+,11-6-
InChI KeyWOIOXNFWBXFNFJ-QTJNYWJXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzepines
Sub ClassNot Available
Direct ParentAzepines
Alternative Parents
Substituents
  • Azepine
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
Water Solubility0.006 g/LALOGPS
logP4.42ALOGPS
logP3.45ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.96 m³·mol⁻¹ChemAxon
Polarizability28.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.90930932474
DeepCCS[M-H]-157.55130932474
DeepCCS[M-2H]-190.43730932474
DeepCCS[M+Na]+166.00230932474
AllCCS[M+H]+161.732859911
AllCCS[M+H-H2O]+157.832859911
AllCCS[M+NH4]+165.432859911
AllCCS[M+Na]+166.432859911
AllCCS[M-H]-165.132859911
AllCCS[M+Na-2H]-165.832859911
AllCCS[M+HCOO]-166.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChalciporoneCCC(=O)CC\C=C\C=C/C1=NC(C)=CC=CC13069.1Standard polar33892256
ChalciporoneCCC(=O)CC\C=C\C=C/C1=NC(C)=CC=CC12140.6Standard non polar33892256
ChalciporoneCCC(=O)CC\C=C\C=C/C1=NC(C)=CC=CC12229.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chalciporone,1TMS,isomer #1CCC(=CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C2387.7Semi standard non polar33892256
Chalciporone,1TMS,isomer #1CCC(=CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C2019.7Standard non polar33892256
Chalciporone,1TMS,isomer #2CC=C(CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C2377.5Semi standard non polar33892256
Chalciporone,1TMS,isomer #2CC=C(CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C2033.2Standard non polar33892256
Chalciporone,1TBDMS,isomer #1CCC(=CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C(C)(C)C2603.4Semi standard non polar33892256
Chalciporone,1TBDMS,isomer #1CCC(=CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C(C)(C)C2259.0Standard non polar33892256
Chalciporone,1TBDMS,isomer #2CC=C(CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C(C)(C)C2584.0Semi standard non polar33892256
Chalciporone,1TBDMS,isomer #2CC=C(CC/C=C/C=C\C1=NC(C)=CC=CC1)O[Si](C)(C)C(C)(C)C2273.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chalciporone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-7920000000-f870195ca88b4a4ef7412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chalciporone 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 - Chalciporone 10V, Positive-QTOFsplash10-0006-1190000000-83cddcad726a414f3fd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 20V, Positive-QTOFsplash10-0a4l-9830000000-07bf4693c61b846a3e6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 40V, Positive-QTOFsplash10-0kxr-9200000000-9807f1309158a6901d462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 10V, Negative-QTOFsplash10-0006-0090000000-851599c0706b38feedf62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 20V, Negative-QTOFsplash10-0006-3290000000-ee561c859c3eb24b53cf2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 40V, Negative-QTOFsplash10-01bc-9210000000-71af61448a34e4c48ed82016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 10V, Positive-QTOFsplash10-0006-0390000000-be1afedc5a183955ff382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 20V, Positive-QTOFsplash10-00g3-1920000000-469f8ee1d86c7de7f39f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 40V, Positive-QTOFsplash10-05xr-3900000000-80eefd2dfebe74a3da422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 10V, Negative-QTOFsplash10-0006-0190000000-41073e9035cbd1d5d2bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 20V, Negative-QTOFsplash10-006x-2970000000-86303768a257aa968abf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalciporone 40V, Negative-QTOFsplash10-0aou-1900000000-d583e618295e458b11322021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB011582
KNApSAcK IDC00055305
Chemspider ID30777015
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751447
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .