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Record Information
Version2.0
Created at2022-04-27 22:36:43 UTC
Updated at2022-04-27 22:36:43 UTC
NP-MRD IDNP0051210
Secondary Accession NumbersNone
Natural Product Identification
Common NameDictamine
DescriptionDictamnine belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Dictamnine was also reported to be a phototoxic and photomutagenic compound. Dictamnine is a strong basic compound (based on its pKa). Dictamnine is a potentially toxic compound. The reaction typically begins within 24 hours of exposure and peaks at 48–72 hours after the exposure. Many different topical and oral medications can be used to treat the inflammatory reaction of phytophotodermatitis. The symptoms are equivalent to photodermatitis, but vary in severity. It is the main alkaloid in the roots of Dictamnus albus and responsible for the mutagenicity of the drug derived from crude extracts. Windows will filter out ultraviolet light and prevent symptoms from arising. Sunblock can greatly mitigate symptoms, at least when caused by rue (Ruta Graveolens). Dictamine is found in Acronychia pedunculata , Acronychia pubescens, Adiscanthus fusciflorus, Aegle marmelos , Afraegle paniculata , Almeidea coerulea, Amyris pinnata, Andreadoxa flava, Balfourodendron riedelianum, Boenninghausenia albiflora , Boronella aff. Verticillata, Boronia bowmanii, Boronia coerulescens spp. Spinescens, Boronia inornata, Boronia pinnata, Bouchardatia neurococca, Casimiroa edulis , Chorilaena quercifolia, Clausena vestita, Comptonella sessilifoliola, Decatropis bicolor, Dictamnus albus , Dictamnus angustifolia, Dictamnus angustifolius, Dictamnus caucasicus, Dictamnus dasycarpus , Drummondita calida, Dutaillyea drupacea, Dutaillyea oreophila, Esenbeckia alata, Esenbeckia febrifuga, Esenbeckia flava, Esenbeckia leiocarpa, Esenbeckia litoralis, Esenbeckia pentaphylla, Esenbeckia spp., Euodia belahe, Euodia fargesii, Euodia lepta , Euodia litoralis, Euodia lunu-ankenda, Euodia macrocarpa, Euodia pachyphylla, Euodia roxburghiana, Melicope pteleifolia , Flindersia acuminate, Flindersia fournieri, Flindersia maculosa, Flindersia pimenteliana, Flindersia pubescens, Flindersia spp., Geijera balansae, Geijera spp., Glycosma spp., Glycosmis biloculares, Glycosmis mauritiana, Glycosmis pentaphylla , Glycosmis trichanthera, Halfordia kendack, Haplophyllum acutifolium, Haplophyllum bucharicum Litv., Haplophyllum bungei, Haplophyllum buxbaumii, Haplophyllum cappadocicum, Haplophyllum coppadocicum, Haplophyllum dauricum, Haplophyllum griffithianum, Haplophyllum myrtifolium, Haplophyllum mytrifolium, Haplophyllum obtusifolium, Haplophyllum ramosissimum, Haplophyllum robustum Bge., Haplophyllum spp., Haplophyllum suaveolens, Haplophyllum vucanicum, Helietta longifoliata, Hortia arborea, Hortia longifolia, Feronia limonia , Medicosma cunninghamii, Melicope indica, Melicope semecarpifolia, Melicope triphylla, Monnieria trifolia, Myrtopsis macrocarpa, Myrtopsis myrtoidea, Myrtopsis novae-caledoniae, Myrtopsis sellingii, Neoraputia paraensis, Phebalium nudum, Phellodendron amurense, Phelodendron amurense, Pilocarpus grandiflorus, Pitavia punctata, Ptelea trifoliata , Raputia heptaphylla, Raputia praetermissa, Ruta angustifolia , Ruta chalepensis L. , Ruta corsica, Ruta graveolens , Ruta montana , Ruta spp., Sarcomelicope argyrophylla, Sarcomelicope dogniensis, Sarcomelicope glauca, Sarcomelicope megistophylla, Skimmia foremanii, Skimmia japonica, Skimmia laureola, Skimmia repens, Spiranthera odoratissima, Teclea amanuensis, Teclea natalensis, Teclea trichocarpa, Tetradium trichotomum, Ticorea longiflora, Toddalia aculeata , Toddalia aculeate var. gracilus, Toddalia asiatica , Zanthoxtlum wutaiense, Zanthoxylum acanthopodium , Zanthoxylum ailanthoides, Zanthoxylum alatum , Zanthoxylum arnottianum, Zanthoxylum austrosinense, Zanthoxylum avicennae , Zanthoxylum beecheyanum, Zanthoxylum belizense, Zanthoxylum bundrunga, Zanthoxylum cuspidatum, Zanthoxylum decaryi, Zanthoxylum dissitum, Zanthoxylum ekmanii, Zanthoxylum inerme, Zanthoxylum integrifoliolum, Zanthoxylum mayu, Zanthoxylum nitidum , Zanthoxylum panispinum, Zanthoxylum parviflorum, Zanthoxylum pistaciiflorum, Zanthoxylum regnellianum, Zanthoxylum scandens, Zanthoxylum schinifolium , Zanthoxylum simulans, Zanthoxylum spp., Zanthoxylum stelligerum and Zanthoxylum wutaiense. This may be accompanied by blisters or burning.
Structure
Thumb
Synonyms
ValueSource
4-methoxyfuro[23-b]QuinolineChEMBL
DictamineChEMBL, MeSH
4-methoxyfuro(2,3-b)QuinolineMeSH
Chemical FormulaC12H9NO2
Average Mass199.2054 Da
Monoisotopic Mass199.06333 Da
IUPAC Name4-methoxyfuro[2,3-b]quinoline
Traditional Namedictamine
CAS Registry NumberNot Available
SMILES
COC1=C2C=COC2=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3
InChI KeyWIONIXOBNMDJFJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acronychia pedunculataPlant
Acronychia pubescensPlant
Adiscanthus fusciflorusPlant
Aegle marmelosPlant
Afraegle paniculataPlant
Almeidea coeruleaPlant
Amyris pinnataPlant
Andreadoxa flavaPlant
Balfourodendron riedelianumPlant
Boenninghausenia albifloraPlant
Boronella aff. VerticillataPlant
Boronia bowmaniiPlant
Boronia coerulescens spp. SpinescensPlant
Boronia inornataPlant
Boronia pinnataPlant
Bouchardatia neurococcaPlant
Casimiroa edulisPlant
Chorilaena quercifolia-
Clausena vestitaLOTUS Database
Comptonella sessilifoliolaPlant
Decatropis bicolor-
Dictamnus albusPlant
Dictamnus angustifoliaPlant
Dictamnus angustifoliusPlant
Dictamnus caucasicusPlant
Dictamnus dasycarpusPlant
Drummondita calidaPlant
Dutaillyea drupaceaPlant
Dutaillyea oreophilaPlant
Esenbeckia alataPlant
Esenbeckia febrifugaLOTUS Database
Esenbeckia flavaPlant
Esenbeckia leiocarpaPlant
Esenbeckia litoralisPlant
Esenbeckia pentaphyllaPlant
Esenbeckia spp.Plant
Euodia belahePlant
Euodia fargesiiPlant
Euodia leptaPlant
Euodia litoralisPlant
Euodia lunu-ankendaPlant
Euodia macrocarpaPlant
Euodia pachyphyllaPlant
Euodia roxburghianaPlant
Evodia leptaPlant
Flindersia acuminatePlant
Flindersia fournieriPlant
Flindersia maculosaPlant
Flindersia pimentelianaPlant
Flindersia pubescensPlant
Flindersia spp.Plant
Geijera balansaePlant
Geijera spp.Plant
Glycosma spp.-
Glycosmis bilocularesPlant
Glycosmis mauritianaPlant
Glycosmis pentaphyllaPlant
Glycosmis trichantheraPlant
Halfordia kendackPlant
Haplophyllum acutifoliumLOTUS Database
Haplophyllum bucharicumPlant
Haplophyllum bungeiPlant
Haplophyllum buxbaumiiPlant
Haplophyllum cappadocicumLOTUS Database
Haplophyllum coppadocicumPlant
Haplophyllum dauricumPlant
Haplophyllum griffithianumLOTUS Database
Haplophyllum myrtifoliumLOTUS Database
Haplophyllum mytrifoliumPlant
Haplophyllum obtusifoliumPlant
Haplophyllum ramosissimumPlant
Haplophyllum robustum Bge.Plant
Haplophyllum spp.Plant
Haplophyllum suaveolensPlant
Haplophyllum vucanicumPlant
Helietta longifoliataPlant
Hortia arboreaPlant
Hortia longifoliaPlant
Limonia acidissimaPlant
Medicosma cunninghamiiPlant
Melicope indicaPlant
Melicope semecarpifoliaPlant
Melicope triphyllaPlant
Monnieria trifoliaPlant
Myrtopsis macrocarpaPlant
Myrtopsis myrtoideaPlant
Myrtopsis novae-caledoniaePlant
Myrtopsis sellingiiPlant
Neoraputia paraensisPlant
Phebalium nudumPlant
Phellodendron amurenseLOTUS Database
Phelodendron amurense-
Pilocarpus grandiflorusPlant
Pitavia punctata-
Ptelea trifoliataPlant
Raputia heptaphyllaPlant
Raputia praetermissaLOTUS Database
Ruta angustifoliaPlant
Ruta chalepensisPlant
Ruta corsicaPlant
Ruta graveolensPlant
Ruta montanaPlant
Ruta spp.Plant
Sarcomelicope argyrophyllaPlant
Sarcomelicope dogniensisPlant
Sarcomelicope glaucaPlant
Sarcomelicope megistophyllaPlant
Skimmia foremaniiPlant
Skimmia japonicaPlant
Skimmia laureolaPlant
Skimmia repensPlant
Spiranthera odoratissima-
Teclea amanuensisPlant
Teclea natalensisPlant
Teclea trichocarpaPlant
Tetradium trichotomumPlant
Ticorea longiflora-
Toddalia aculeataPlant
Toddalia aculeate var. gracilusPlant
Toddalia asiaticaPlant
Zanthoxtlum wutaiense-
Zanthoxylum acanthopodiumPlant
Zanthoxylum ailanthoidesPlant
Zanthoxylum alatumPlant
Zanthoxylum arnottianumPlant
Zanthoxylum austrosinensePlant
Zanthoxylum avicennaePlant
Zanthoxylum beecheyanumLOTUS Database
Zanthoxylum belizensePlant
Zanthoxylum bundrungaPlant
Zanthoxylum cuspidatumPlant
Zanthoxylum decaryiPlant
Zanthoxylum dissitumPlant
Zanthoxylum ekmaniiPlant
Zanthoxylum inermePlant
Zanthoxylum integrifoliolumPlant
Zanthoxylum mayuPlant
Zanthoxylum nitidumPlant
Zanthoxylum panispinumPlant
Zanthoxylum parviflorumPlant
Zanthoxylum pistaciiflorumPlant
Zanthoxylum regnellianumPlant
Zanthoxylum scandensLOTUS Database
Zanthoxylum schinifoliumPlant
Zanthoxylum simulansPlant
Zanthoxylum spp.Plant
Zanthoxylum stelligerumPlant
Zanthoxylum wutaiensePlant
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002151
Chemspider IDNot Available
KEGG Compound IDC10660
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68085
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available