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
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-ce0c9de9daa7ecc957fe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0609000000-3e7b629c694247ab37fe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-1900000000-02589253879ac72317672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c7ed985cf580bb10595d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0009000000-2562c02bc56526e790dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-6269000000-7d9c64483d5fb3c074672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-ad1696003a3beba4181b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-d594dd1aaea05b7b05f32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-0079000000-c98f187cb22bdb279ca12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c0b0af865b3879fc49f62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-7072102416df1e826f052021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0049000000-df41ddb5e7027542be332021-10-21View Spectrum
NMRNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).