Record Information
Version1.0
Creation date2010-04-08 22:06:50 UTC
Update date2019-11-26 03:00:45 UTC
Primary IDFDB005759
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Allocryptopine
DescriptionAlpha-allocryptopine, also known as alpha-fagarine or beta-homochelidonine, is a member of the class of compounds known as protopine alkaloids. Protopine alkaloids are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Alpha-allocryptopine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-allocryptopine can be found in barley, which makes alpha-allocryptopine a potential biomarker for the consumption of this food product.
CAS Number485-91-6
Structure
Thumb
Synonyms
SynonymSource
5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methyl(1,3)benzodioxolo(5,6-e)(2)benzazecin-14(6H)-oneChEBI
alpha-FagarineChEBI
beta-HomochelidonineChEBI
ThalictrimineChEBI
a-FagarineGenerator
Α-fagarineGenerator
b-HomochelidonineGenerator
Β-homochelidonineGenerator
a-AllocryptopineGenerator
Α-allocryptopineGenerator
Allo-cryptopineMeSH
alpha-AllocryptopineChEBI
α-allocryptopinebiospider
α-fagarinebiospider
β-homochelidoninebiospider
Allocryptopinebiospider
Allocrytopinebiospider
Beta-allocryptopinebiospider
Fagarine Ibiospider
Gamma-homochelidoninebiospider
Taliktrimin (thalictrimine)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP2.38ALOGPS
logP2.65ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.73 m³·mol⁻¹ChemAxon
Polarizability39.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H23NO5
IUPAC name7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0⁴,⁹.0¹⁶,²⁰]henicosa-1(14),4(9),5,7,15,20-hexaen-2-one
InChI IdentifierInChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
InChI KeyHYBRYAPKQCZIAE-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C2=C(CC(=O)C3=C(CCN(C)C2)C=C2OCOC2=C3)C=C1
Average Molecular Weight369.411
Monoisotopic Molecular Weight369.157622851
Classification
Description belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtopine alkaloids
Sub ClassNot Available
Direct ParentProtopine alkaloids
Alternative Parents
Substituents
  • Protopine skeleton
  • Benzodioxole
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Acetal
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point160.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-ce0c9de9daa7ecc957feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0609000000-3e7b629c694247ab37feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-1900000000-02589253879ac7231767JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c7ed985cf580bb10595dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0009000000-2562c02bc56526e790ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-6269000000-7d9c64483d5fb3c07467JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC02134
Pubchem Compound ID98570
Pubchem Substance IDNot Available
ChEBI ID17390
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDALPHA-ALLOCRYPTOPINE
BIGG IDNot Available
KNApSAcK IDC00001799
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cardioactive38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
oxytocic36063 A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).