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Record Information
Version2.0
Creation Date2014-08-29 05:04:05 UTC
Update Date2014-12-24 20:26:38 UTC
Accession NumberT3D4081
Identification
Common NameMatrine
ClassSmall Molecule
DescriptionMatrine is an alkaloid found in plants from the Sophora genus. It has a variety of pharmacological effects, including anti-cancer effects, and action as a kappa opioid receptor and μ-receptor agonist.
Compound Type
  • Amide
  • Amine
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(+)-Matrine
Matridin-15-one
Sophoridine
Chemical FormulaC15H24N2O
Average Molecular Mass248.364 g/mol
Monoisotopic Mass248.189 g/mol
CAS Registry Number519-02-8
IUPAC Name(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one
Traditional Namematrine
SMILES[H][C@]12CCCN3CCC[C@]([H])([C@@]4([H])CCCC(=O)N4C1)[C@]23[H]
InChI IdentifierInChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-/m0/s1
InChI KeyInChIKey=ZSBXGIUJOOQZMP-JLNYLFASSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassLupin alkaloids
Sub ClassMatrine alkaloids
Direct ParentMatrine alkaloids
Alternative Parents
Substituents
  • Matrine
  • Quinolizidinone
  • Diazanaphthalene
  • Naphthyridine
  • Quinolizidine
  • Delta-lactam
  • Piperidinone
  • Piperidine
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Cytoplasm
  • Cytosol
  • Endoplasmic reticulum
  • Extracellular
  • Extracellular matrix
  • Lysosome
  • Mitochondrion
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Cell cycleNot Availablemap04110
Gastric acid secretionNot Availablemap04971
Nf-kappa b signaling pathwayNot Availablemap04064
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.24 g/LALOGPS
logP1.92ALOGPS
logP1.08ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.45 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-8ee63c2a1c35de3fff22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-4f7ecba727c2ca8097caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-2930000000-b8e4ecbc12721437841bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-274cc1f6bff7ae2cfb7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-dc7aab170fe29e23e17aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0036-5970000000-88a546869c5bb0c632d9JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-052b-9630000000-eed96cedc2334a0b0d1eJSpectraViewer | MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe nervous system is the main target organ by the toxicity of matrine. Morphological observation revealed degenerative changes of the nerve cells in the brain tissue of the mice. (1) Matrine has a variety of pharmacological effects, including anti-cancer effects, and action as a kappa opioid receptor and µ-receptor agonist. Matrine possesses strong antitumor activities in vitro and in vivo. Inhibition of cell proliferation and induction of apoptosis are the likely mechanisms responsible for matrine's antitumor activities. (Wikipedia)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMatrine is an alkaloid found in plants from the Sophora genus.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID91466
ChEMBL IDCHEMBL204860
ChemSpider ID82591
KEGG IDC10774
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
MSDST3D4081.pdf
General References
  1. Wang XY, Liang L, Chang JL, Yang MH, Li ZG: [Toxicity of matrine in Kunming mice]. Nan Fang Yi Ke Da Xue Xue Bao. 2010 Sep;30(9):2154-5. [20855277 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available