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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:05:55 UTC
Update Date2021-09-26 23:10:16 UTC
HMDB IDHMDB0255458
Secondary Accession NumbersNone
Metabolite Identification
Common NameNarciclasine
DescriptionNarciclasine belongs to the class of organic compounds known as phenanthridine- and phenanthridone-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds based on the phenanthridine or the phenanthridone skeleton. Phenanthridone-type alkaloids have the highest oxygenated C ring in all Amaryllidaceae alkaloids, and they always show an amide group in ring B. On the contrary, alkaloids of the phenanthridine type often show completely aromatic ring system, occasionally with a methylation quaternary nitrogen atom. Based on a literature review a significant number of articles have been published on Narciclasine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Narciclasine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Narciclasine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H13NO7
Average Molecular Weight307.258
Monoisotopic Molecular Weight307.069201763
IUPAC Name4,5,6,11-tetrahydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2,10,12(16)-tetraen-9-one
Traditional Name4,5,6,11-tetrahydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2,10,12(16)-tetraen-9-one
CAS Registry NumberNot Available
SMILES
OC1C=C2C(NC(=O)C3=C(O)C4=C(OCO4)C=C23)C(O)C1O
InChI Identifier
InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)
InChI KeyLZAZURSABQIKGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthridine- and phenanthridone-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds based on the phenanthridine or the phenanthridone skeleton. Phenanthridone-type alkaloids have the highest oxygenated C ring in all Amaryllidaceae alkaloids, and they always show an amide group in ring B. On the contrary, alkaloids of the phenanthridine type often show completely aromatic ring system, occasionally with a methylation quaternary nitrogen atom.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassPhenanthridine- and phenanthridone-type amaryllidaceae alkaloids
Direct ParentPhenanthridine- and phenanthridone-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Phenanthridone-type amaryllidaceae alkaloid
  • Benzoquinoline
  • Phenanthridine
  • Isoquinolone
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Cyclitol or derivatives
  • Benzenoid
  • Vinylogous acid
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Polyol
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID538000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNarciclasine
METLIN IDNot Available
PubChem Compound619061
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]