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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:13:42 UTC
Update Date2022-03-07 02:57:03 UTC
HMDB IDHMDB0041537
Secondary Accession Numbers
  • HMDB41537
Metabolite Identification
Common NameN-Acetyldehydroanonaine
DescriptionN-Acetyldehydroanonaine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. N-Acetyldehydroanonaine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-acetyldehydroanonaine has been detected, but not quantified in, fruits and herbs and spices. This could make N-acetyldehydroanonaine a potential biomarker for the consumption of these foods.
Structure
Data?1563863674
SynonymsNot Available
Chemical FormulaC19H15NO3
Average Molecular Weight305.3273
Monoisotopic Molecular Weight305.105193351
IUPAC Name1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethan-1-one
Traditional Name1-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaen-11-yl}ethanone
CAS Registry Number132646-11-8
SMILES
CC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31
InChI Identifier
InChI=1S/C19H15NO3/c1-11(21)20-7-6-13-9-16-19(23-10-22-16)18-14-5-3-2-4-12(14)8-15(20)17(13)18/h2-5,8-9H,6-7,10H2,1H3
InChI KeyFNUSCCFSHRMQQM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Benzodioxole
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Acetamide
  • Carboxamide group
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point151 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.27ALOGPS
logP2.72ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.01 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.89731661259
DarkChem[M-H]-166.10931661259
DeepCCS[M-2H]-196.44830932474
DeepCCS[M+Na]+171.61930932474
AllCCS[M+H]+170.232859911
AllCCS[M+H-H2O]+166.732859911
AllCCS[M+NH4]+173.532859911
AllCCS[M+Na]+174.432859911
AllCCS[M-H]-178.032859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-176.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetyldehydroanonaineCC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C314168.3Standard polar33892256
N-AcetyldehydroanonaineCC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C312818.3Standard non polar33892256
N-AcetyldehydroanonaineCC(=O)N1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C313178.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldehydroanonaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1090000000-3be673e829379007b4c12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldehydroanonaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldehydroanonaine 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 - N-Acetyldehydroanonaine 10V, Positive-QTOFsplash10-0a4i-0039000000-83c85b4aa3856db47e512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Positive-QTOFsplash10-0bt9-0096000000-81087b256ded869c66062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Positive-QTOFsplash10-02ai-1090000000-9090f6814cf5889e31fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Negative-QTOFsplash10-0udi-0029000000-821ad62da85eb995cd652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Negative-QTOFsplash10-0ik9-1095000000-62a257d4823339b4c9722017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Negative-QTOFsplash10-03di-2090000000-7d6c990d913f488afc182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Negative-QTOFsplash10-0udi-0029000000-0d43d345fce52165f59f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Negative-QTOFsplash10-0ik9-0097000000-0bc82a3ee74aa2993fd82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Negative-QTOFsplash10-0il3-1092000000-6c48d0c524a338010bf72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 10V, Positive-QTOFsplash10-0a4i-0009000000-43ab62a80b50d00d6e5f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 20V, Positive-QTOFsplash10-0a4i-0039000000-1a45e8f62fa161f99e432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldehydroanonaine 40V, Positive-QTOFsplash10-000i-0090000000-e78fd1902ec5c130217d2021-09-24Wishart 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 IDFDB021517
KNApSAcK IDNot Available
Chemspider ID4474975
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315739
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.. .