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Showing Compound (S)-Dicentrine (FDB002141)

Record Information
Version1.0
Creation date2010-04-08 22:05:15 UTC
Update date2025-11-18 22:35:13 UTC
Primary IDFDB002141
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Dicentrine
Description(s)-dicentrine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof (s)-dicentrine is practically insoluble (in water) and a very strong basic compound (based on its pKa). (s)-dicentrine can be found in barley, which makes (s)-dicentrine a potential biomarker for the consumption of this food product.
CAS Number517-66-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Dicentrine, (R)-isomerMeSH
DicentrineMeSH
Dicentrine nitrate, (S)-isomerMeSH
(R)-(-)-DicentrineMeSH
L-DicentrineMeSH
1, 2-Methylenedioxy-9,10-dimethoxyaporphinebiospider
1,2-Methylenedioxy-9,10-dimethoxyaporphinebiospider
6a-alpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-biospider
6aα-Aporphine, 9, 10-dimethoxy-1,2-(methylenedioxy)-biospider
6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-biospider
9,10-Dimethoxy-1, 2-(methylenedioxy)aporphinebiospider
9,10-Dimethoxy-1,2-(methylenedioxy)aporphinebiospider
D-dicentrinebiospider
Dicentrine-(+)biospider
Eximinebiospider
O,n-dimethyllitseferinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP2.76ALOGPS
logP3.01ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.72 m³·mol⁻¹ChemAxon
Polarizability37.53 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H21NO4
IUPAC name16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene
InChI IdentifierInChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3
InChI KeyYJWBWQWUHVXPNC-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1OC)C1=C3C(C2)N(C)CCC3=CC2=C1OCO2
Average Molecular Weight339.385
Monoisotopic Molecular Weight339.147058165
Classification
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
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Acetal
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.78%; H 6.24%; N 4.13%; O 18.86%DFC
Melting PointMp 168-169°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +57 (c, 1 in EtOH)DFC
Spectroscopic UV Data305 (log e 4.23) (95% EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fs-0079000000-8db4ef7d343883503869Spectrum
Predicted GC-MS(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-1f81863145e9ffb305312019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0029000000-18a221817aeaa6f459a42019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00am-0091000000-4722e1ecc495d0883f412019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-26e8f0a6ebd0ceac8b582019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-4a39f762b3f502df7e612019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gvo-0090000000-96836bde115a621f735f2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-952964009ca467e588252021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-c196527b93bff46d89262021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1097000000-0843fef05443ced7b8582021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-a9f00908271fb71883c32021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000000-e204e48d446354e251f22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-0095000000-97541ac35b8b324e281a2021-10-12View Spectrum
NMRNot Available
ChemSpider ID547811
ChEMBL IDNot Available
KEGG Compound IDC17426
Pubchem Compound ID101300
Pubchem Substance IDNot Available
ChEBI ID581347
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCFZ32-I:CFZ34-K
EAFUS IDNot Available
Dr. Duke IDDICENTRINE
BIGG IDNot Available
KNApSAcK IDC00025658
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
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti convulsant52217 An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.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).