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Record Information
Version2.0
Created at2022-04-28 01:17:38 UTC
Updated at2022-04-28 01:17:38 UTC
NP-MRD IDNP0055158
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Matrine N-oxide
DescriptionOxymatrine 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. (+)-Matrine N-oxide is found in Ammothamnus lehmanni, Ammothamnus songoricus, Corydalis yanhusuo , Daphniphyllum oldhami, Genista aucheri, Sophora alopecuroides, Sophora davidii, Sophora flavescens , Sophora flavescens var. angustifolia , Sophora moorcroftiana Benth. , Sophora pachycarpa Schrenk., Sophora subprostate, Sophora subprostrata, Sophora tonkinensis, Sophora viciifolia and Sophorae flavescentis. (+)-Matrine N-oxide was first documented in 2021 (PMID: 35252223). Based on a literature review a small amount of articles have been published on Oxymatrine (PMID: 35335977) (PMID: 35432866) (PMID: 35310033) (PMID: 35290143).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H24N2O2
Average Mass264.3690 Da
Monoisotopic Mass264.18378 Da
IUPAC Name(1R,2R,9S,13R,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-13-ium-13-olate
Traditional Name(1R,2R,9S,13R,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-13-ium-13-olate
CAS Registry NumberNot Available
SMILES
[O-][N@+]12CCC[C@H]3CN4[C@H](CCCC4=O)[C@@H](CCC1)[C@@H]23
InChI Identifier
InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17+/m0/s1
InChI KeyXVPBINOPNYFXID-JARXUMMXSA-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
Ammothamnus lehmanniPlant
Ammothamnus songoricusPlant
Corydalis yanhusuoPlant
Daphniphyllum oldhamiiPlant
Genista aucheriPlant
Sophora alopecuroidesPlant
Sophora davidiiLOTUS Database
Sophora flavescensPlant
Sophora flavescens var. angustifoliaPlant
Sophora moorcroftiana Benth.Plant
Sophora pachycarpa Schrenk.Plant
Sophora subprostatePlant
Sophora subprostrataPlant
Sophora tonkinensisPlant
Sophora viciifoliaPlant
Sophorae flavescentis-
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
  • Quinolizidine
  • Naphthyridine
  • Piperidinone
  • Delta-lactam
  • Piperidine
  • Trialkyl amine oxide
  • Tertiary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Trisubstituted n-oxide
  • Carboxylic acid derivative
  • N-oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP-0.33ALOGPS
logP-0.048ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)3.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.49 m³·mol⁻¹ChemAxon
Polarizability29.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007758
Chemspider ID29273181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxymatrine
METLIN IDNot Available
PubChem Compound24864132
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hu D, Chen X, Li D, Zhang H, Duan Y, Huang Y: Sustained Release of Co-Amorphous Matrine-Type Alkaloids and Resveratrol with Anti-COVID-19 Potential. Pharmaceutics. 2022 Mar 10;14(3). pii: pharmaceutics14030603. doi: 10.3390/pharmaceutics14030603. [PubMed:35335977 ]
  2. Kikuchi T, Ogawa M, Okamura T, Gee AD, Zhang MR: Rapid 'on-column' preparation of hydrogen [(11)C]cyanide from [(11)C]methyl iodide via [(11)C]formaldehyde. Chem Sci. 2022 Mar 8;13(12):3556-3562. doi: 10.1039/d1sc07033a. eCollection 2022 Mar 24. [PubMed:35432866 ]
  3. Aryal B, Raut BK, Bhattarai S, Bhandari S, Tandan P, Gyawali K, Sharma K, Ranabhat D, Thapa R, Aryal D, Ojha A, Devkota HP, Parajuli N: Potential Therapeutic Applications of Plant-Derived Alkaloids against Inflammatory and Neurodegenerative Diseases. Evid Based Complement Alternat Med. 2022 Mar 9;2022:7299778. doi: 10.1155/2022/7299778. eCollection 2022. [PubMed:35310033 ]
  4. Li S, Feng G, Zhang M, Zhang X, Lu J, Feng C, Zhu F: Oxymatrine attenuates TNBS-induced colinutis in rats through TLR9/Myd88/NF-kappaB signal pathway. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221078866. doi: 10.1177/09603271221078866. [PubMed:35290143 ]
  5. Das A, Kashyap O, Singh A, Shree J, Namdeo KP, Bodakhe SH: Oxymatrine Protects TGFbeta1-Induced Retinal Fibrosis in an Animal Model of Glaucoma. Front Med (Lausanne). 2022 Feb 18;8:750342. doi: 10.3389/fmed.2021.750342. eCollection 2021. [PubMed:35252223 ]