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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:10:55 UTC
Update Date2022-03-07 02:53:42 UTC
HMDB IDHMDB0033447
Secondary Accession Numbers
  • HMDB33447
Metabolite Identification
Common NameRetrofractamide A
DescriptionRetrofractamide A belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Retrofractamide A has been detected, but not quantified in, herbs and spices and pepper (spice). This could make retrofractamide a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Retrofractamide A.
Structure
Data?1563862407
Synonyms
ValueSource
(2E,4E,8E)-9-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienimidateHMDB
Retrofractamide aMeSH
Chemical FormulaC20H25NO3
Average Molecular Weight327.4174
Monoisotopic Molecular Weight327.183443671
IUPAC Name(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide
Traditional Name(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide
CAS Registry Number94079-67-1
SMILES
CC(C)CNC(=O)\C=C\C=C\CC\C=C\C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C20H25NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h4,6-13,16H,3,5,14-15H2,1-2H3,(H,21,22)/b6-4+,9-7+,10-8+
InChI KeyBPSWISYORIWKCT-FCGWLDPVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Styrene
  • N-acyl-amine
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP4.6ALOGPS
logP4.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.13 m³·mol⁻¹ChemAxon
Polarizability39.09 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]+182.1730932474
DeepCCS[M-H]-179.76630932474
DeepCCS[M-2H]-213.83130932474
DeepCCS[M+Na]+189.67630932474
AllCCS[M+H]+182.332859911
AllCCS[M+H-H2O]+179.232859911
AllCCS[M+NH4]+185.132859911
AllCCS[M+Na]+185.932859911
AllCCS[M-H]-184.732859911
AllCCS[M+Na-2H]-185.132859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Retrofractamide ACC(C)CNC(=O)\C=C\C=C\CC\C=C\C1=CC2=C(OCO2)C=C14426.2Standard polar33892256
Retrofractamide ACC(C)CNC(=O)\C=C\C=C\CC\C=C\C1=CC2=C(OCO2)C=C12777.9Standard non polar33892256
Retrofractamide ACC(C)CNC(=O)\C=C\C=C\CC\C=C\C1=CC2=C(OCO2)C=C13074.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Retrofractamide A,1TMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C2919.0Semi standard non polar33892256
Retrofractamide A,1TMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C2853.8Standard non polar33892256
Retrofractamide A,1TBDMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C3110.7Semi standard non polar33892256
Retrofractamide A,1TBDMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C3061.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Retrofractamide A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3970000000-5d36ba25b22723f87ff62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Retrofractamide A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Retrofractamide A 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 - Retrofractamide A 10V, Positive-QTOFsplash10-00di-9013000000-3bd2c1b80a6f51dd783a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 20V, Positive-QTOFsplash10-00di-9010000000-12c1bc9e6cb70e96d0252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 40V, Positive-QTOFsplash10-0ab9-9000000000-14abe4bf505c5d238e2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 10V, Negative-QTOFsplash10-004i-1039000000-05a6d1b1ed52dc3ed0ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 20V, Negative-QTOFsplash10-00b9-4195000000-aecd27d31bfd96f63eaa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 40V, Negative-QTOFsplash10-00fu-8190000000-897886e75bf5a2ced3c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 10V, Positive-QTOFsplash10-004i-0019000000-26d9ba1a8d2641c463a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 20V, Positive-QTOFsplash10-0a6r-5393000000-582f69d552ca2ec7269c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 40V, Positive-QTOFsplash10-03dj-6970000000-b2a3de7a57a95856d9a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 10V, Negative-QTOFsplash10-004i-0019000000-e2c58c4ec6ef810cd4462021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 20V, Negative-QTOFsplash10-00b9-3139000000-5b4490871b6be1584adc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retrofractamide A 40V, Negative-QTOFsplash10-0005-8921000000-a7c25472d41907f82cc12021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB011485
KNApSAcK IDC00034654
Chemspider ID9188045
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11012859
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.. .