Record Information
Version1.0
Creation date2010-04-08 22:05:15 UTC
Update date2018-01-25 19:29:02 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
Synonyms
SynonymSource
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
Dicentrinebiospider
Dicentrine-(+)biospider
Eximinebiospider
O,n-dimethyllitseferinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.081 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound 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
  • Benzylisoquinoline
  • Phenanthrene
  • Benzoquinoline
  • Tetrahydroisoquinoline
  • Quinoline
  • Naphthalene
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-1f81863145e9ffb30531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0029000000-18a221817aeaa6f459a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00am-0091000000-4722e1ecc495d0883f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-26e8f0a6ebd0ceac8b58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-4a39f762b3f502df7e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gvo-0090000000-96836bde115a621f735fView in MoNA
ChemSpider IDNot Available
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
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 capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.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).