Dictamnine (T3D4080)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:03:55 UTC
Update Date2014-12-24 20:26:38 UTC
Accession NumberT3D4080
Identification
Common NameDictamnine
ClassSmall Molecule
DescriptionA furoquinoline alkaloid, dictamnine, is very common within the family Rutaceae. It is the main alkaloid in the roots of Dictamnus albus and responsible for the mutagenicity of the drug derived from crude extracts. Dictamnine was also reported to be a phototoxic and photomutagenic compound. It participates in the severe skin phototoxicity of the plant.
Compound Type
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
4-Methoxyfuro[2,3-b]Quinoline
Dictamine
Chemical FormulaC12H9NO2
Average Molecular Mass199.205 g/mol
Monoisotopic Mass199.063 g/mol
CAS Registry Number484-29-7
IUPAC Name4-methoxyfuro[2,3-b]quinoline
Traditional Namedictamine
SMILESCOC1=C2C=COC2=NC2=CC=CC=C12
InChI IdentifierInChI=1S/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3
InChI KeyInChIKey=WIONIXOBNMDJFJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassFuranoquinolines
Direct ParentFuranoquinolines
Alternative Parents
Substituents
  • Furanoquinoline
  • Furopyridine
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite crystal powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.78ALOGPS
logP2.5ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)3.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.26 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.24 m³·mol⁻¹ChemAxon
Polarizability20.47 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0900000000-072b856200222c8d01312021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0950000000-61a806bd0e9b7d6881452021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-6876e7ccfa4e8d41dbc02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-b8d64ef0fc66a9c9819d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-0cde04c46eb7f9e5c76d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-11d35fc084ae76547ff42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-0910000000-be0f3a1eaf0d887d176f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-82f07b36ca0fcbe879442016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-96480e0710e2f31565ad2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-fcb782692dc251c8feb42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-57f642a9b1b9aed9bd5a2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-57f642a9b1b9aed9bd5a2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-c5ebe34a280d867d17672021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-9b133ffd69fbc0c82dc92021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-9b133ffd69fbc0c82dc92021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0490000000-e6a776b0fbea8cfb970c2021-10-12View Spectrum
Toxicity Profile
Route of ExposureDermal
Mechanism of ToxicityDictamnine has been shown to be phototoxic to human cell lines (namely Jurkat T cells and HaCaT keratinocytes). Although it is less phototoxic than the structurally related furocoumarins 5-methoxypsoralen and 8-methoxypsoralen, "it may play a major role in the elicitation of phytophotodermatitis because of its abundance in plants of the Rutaceae family." (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDictamnine is the main alkaloid in the roots of Dictamnus albus, and occurs in other plants of the Rutaceae family. Dictamnine has been reported to have antimicrobial activity against bacteria and fungi. Dictamnine has anti-platelet aggregation and vascular-relaxing activities, insecticidal activities, phototoxicity to bacteria and yeast and antibacterial activity against Mycobacterium smegmatis and Bacillus subtilis. Dictamnine has also been widely used to treat certain skin diseases. (2)
Minimum Risk LevelNot Available
Health EffectsDictamnine may play a major role in the elicitation of phytophotodermatitis (1). Phytophotodermatitis, also known as "Lime Disease" (not to be confused with Lyme Disease), "Berloque dermatitis", or "Margarita photodermatitis" is a chemical reaction which makes skin hypersensitive to ultraviolet light. It is caused by contact with photosensitizing compounds. (Wikipedia)
SymptomsThe symptoms are equivalent to photodermatitis, but vary in severity. The skin condition is a cutaneous phototoxic inflammatory eruption resulting from contact with light-sensitizing botanical substances—particularly from the plant families Umbelliferae, Rutaceae, Moraceae, and Leguminosae—and ultraviolet light, typically from sun exposure. Phytophotodermatitis usually results in hyperpigmentation of the skin that often appears like a bruise. This may be accompanied by blisters or burning. The reaction typically begins within 24 hours of exposure and peaks at 48–72 hours after the exposure. (Wikipedia)
TreatmentPhytophotodermatitis can be prevented by staying indoors after handling dictamnine. Windows will filter out ultraviolet light and prevent symptoms from arising. Many different topical and oral medications can be used to treat the inflammatory reaction of phytophotodermatitis. A dermatologist may also prescribe a bleaching cream to help treat the hyperpigmentation and return the skin pigmentation back to normal. If they do not receive treatment, the affected sites may develop permanent hyperpigmentation or hypo pigmentation. Sunblock can greatly mitigate symptoms, at least when caused by rue (Ruta Graveolens). (Wikipedia)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID68085
ChEMBL IDCHEMBL22533
ChemSpider ID61397
KEGG IDC10660
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Schempp CM, Simon-Haarhaus B, Krieger R, Simon JC: Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen. Planta Med. 2006 Aug;72(10):941-3. [16972199 ]
  2. Guo N, Yu L, Meng R, Fan J, Wang D, Sun G, Deng X: Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine. Yeast. 2008 Sep;25(9):631-41. doi: 10.1002/yea.1614. [18727144 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available