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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:16 UTC
Update Date2022-03-07 02:52:31 UTC
HMDB IDHMDB0030348
Secondary Accession Numbers
  • HMDB30348
Metabolite Identification
Common NameAnonaine
DescriptionAnonaine 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. Anonaine is a very strong basic compound (based on its pKa). The filtrate can then made basic with NH4OH and extracted with diethyl ether. Outside of the human body, anonaine is found, on average, in the highest concentration in custard apples. anonaine has also been detected, but not quantified in, several different foods, such as cherimoya, fruits, sacred lotus, sugar apples, and tea. This could make anonaine a potential biomarker for the consumption of these foods. It has since been found in Annona squamosa, the leaves of Michelia × alba, Fissistigma latifolium and Goniothalamus australis, among many others. The anonaine content of Annona reticulata is approximately 0.12%, based on the weight of the starting dried bark. Anonaine is a bioactive benzylisoquinoline alkaloid, present in members of the plant families Magnoliaceae and Annonaceae It is named after the plant it was first extracted from, Annona reticulata, which is commonly known as Anona. It appears, however, that anonaine is not active in the treatment of many of these ailments. For example, extracts of Annona squamosa have been used as treatments for epilepsy, dysentery, cardiac problems, worm infection, constipation, bacterial infection, fever and ulcers. The hydrogen chloride salt is then obtained by mixing with hydrochloric acid and recrystallized from diethyl ether. The methanol is removed and the resulting syrup is then treated with hydrochloric acid and the insoluble salts filtered off.
Structure
Data?1563861972
Synonyms
ValueSource
(-)-AnnonaineHMDB
1,2-MethylenedioxynoraporphineHMDB
AnonainHMDB
Chemical FormulaC17H15NO2
Average Molecular Weight265.3065
Monoisotopic Molecular Weight265.110278729
IUPAC Name3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene
Traditional Name3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene
CAS Registry Number1862-41-5
SMILES
C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2
InChI Identifier
InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2
InChI KeyVZTUKBKUWSHDFM-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122 - 123 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP2.22ALOGPS
logP2.94ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)9.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area30.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity76.5 m³·mol⁻¹ChemAxon
Polarizability29.11 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]+160.76731661259
DarkChem[M-H]-158.73131661259
DeepCCS[M-2H]-195.66230932474
DeepCCS[M+Na]+170.82830932474
AllCCS[M+H]+162.032859911
AllCCS[M+H-H2O]+158.232859911
AllCCS[M+NH4]+165.532859911
AllCCS[M+Na]+166.532859911
AllCCS[M-H]-169.232859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-167.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnonaineC1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C23630.8Standard polar33892256
AnonaineC1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C22372.7Standard non polar33892256
AnonaineC1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C22590.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anonaine,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C132533.6Semi standard non polar33892256
Anonaine,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C132513.4Standard non polar33892256
Anonaine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C132759.2Semi standard non polar33892256
Anonaine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C132756.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anonaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-0290000000-eef0189b19c023e625122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anonaine 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 - Anonaine 10V, Positive-QTOFsplash10-014i-0090000000-e9a2afab256159ae26992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 20V, Positive-QTOFsplash10-014i-0090000000-f7ca3522e83754962ac62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 40V, Positive-QTOFsplash10-00pl-1980000000-a0014a6236a9bf51d76e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 10V, Negative-QTOFsplash10-03di-0090000000-74185903329bd522c04a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 20V, Negative-QTOFsplash10-03di-0090000000-7de3784592381bb7a8622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 40V, Negative-QTOFsplash10-014m-1490000000-2f75c30aa943164353af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 10V, Positive-QTOFsplash10-014i-0090000000-4ceb63c2dd5efc77f44c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 20V, Positive-QTOFsplash10-014i-0090000000-4ceb63c2dd5efc77f44c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 40V, Positive-QTOFsplash10-00ds-0190000000-9a10adc3866934e256bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 10V, Negative-QTOFsplash10-03di-0090000000-f67efedff389fe87473b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 20V, Negative-QTOFsplash10-03di-0090000000-e7468aac66a5ed55954f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anonaine 40V, Negative-QTOFsplash10-000t-0090000000-d457525b01f969160b5d2021-09-24Wishart 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 IDFDB002193
KNApSAcK IDC00027281
Chemspider ID2704037
KEGG Compound IDC09339
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnonaine
METLIN IDNot Available
PubChem Compound3462225
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. Paulo Mde Q, Barbosa-Filho JM, Lima EO, Maia RF, Barbosa Rde C, Kaplan MA: Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C. J Ethnopharmacol. 1992 Feb;36(1):39-41. [PubMed:1501491 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .