Np mrd loader

Record Information
Version2.0
Created at2022-09-04 07:32:52 UTC
Updated at2022-09-04 07:32:53 UTC
NP-MRD IDNP0190806
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol
DescriptionCodonopsinine belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol is found in Codonopsis clematidea. (2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol was first documented in 2015 (PMID: 25710030). Based on a literature review a small amount of articles have been published on Codonopsinine (PMID: 31347622) (PMID: 30777662) (PMID: 26883393) (PMID: 26771920).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC13H19NO3
Average Mass237.2990 Da
Monoisotopic Mass237.13649 Da
IUPAC Name(2R,3R,4R,5R)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol
Traditional Name(2R,3R,4R,5R)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1)[C@@H]1[C@@H](O)[C@H](O)[C@@H](C)N1C
InChI Identifier
InChI=1S/C13H19NO3/c1-8-12(15)13(16)11(14(8)2)9-4-6-10(17-3)7-5-9/h4-8,11-13,15-16H,1-3H3/t8-,11-,12-,13-/m1/s1
InChI KeyGJZNAEFHIYPPEM-HUXSOILUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Codonopsis clematideaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
Alternative Parents
Substituents
  • 2-phenylpyrrolidine
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrole
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • 1,2-diol
  • Tertiary amine
  • Azacycle
  • Ether
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.8ChemAxon
pKa (Strongest Acidic)13.22ChemAxon
pKa (Strongest Basic)8.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.11 m³·mol⁻¹ChemAxon
Polarizability26.03 ųChemAxon
Number of Rings2ChemAxon
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 IDNot Available
Chemspider ID9065209
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10889945
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pandey G, Laha R, Mondal PK: Heterocyclization involving benzylic C(sp(3))-H functionalization enabled by visible light photoredox catalysis. Chem Commun (Camb). 2019 Aug 21;55(65):9689-9692. doi: 10.1039/c9cc04287c. Epub 2019 Jul 26. [PubMed:31347622 ]
  2. El-Nezhawy AOH, Alrobaian M, Khames A, El-Badawy MF, Abdelwahab SF: Design and total synthesis of (-)-codonopsinine, (-)-codonopsine and codonopsinine analogues by O-(2-oxopyrrolidin-5-yl)trichloroacetimidate as amidoalkylating agent with improved antimicrobial activity via solid lipid nanoparticle formulations. Bioorg Med Chem. 2019 Apr 1;27(7):1263-1273. doi: 10.1016/j.bmc.2019.02.021. Epub 2019 Feb 13. [PubMed:30777662 ]
  3. Yamaguchi M, Itagaki D, Ueda H, Tokuyama H: Total syntheses of codonopsinine and 4-epi-codonopsinine via gold-mediated tandem-catalyzed pyrrole synthesis. J Antibiot (Tokyo). 2016 Apr;69(4):253-8. doi: 10.1038/ja.2016.13. Epub 2016 Feb 17. [PubMed:26883393 ]
  4. Lingamurthy M, Jagadeesh Y, Ramakrishna K, Rao BV: DDQ-Promoted Benzylic/Allylic sp(3) C-H Activation for the Stereoselective Intramolecular C-N Bond Formation: Applications to the Total Synthesis of (-)-Codonopsinine, (+)-5-epi-Codonopsinine, (+)-Radicamine B, and (-)-Codonopsinol. J Org Chem. 2016 Feb 19;81(4):1367-77. doi: 10.1021/acs.joc.5b02275. Epub 2016 Jan 29. [PubMed:26771920 ]
  5. Johari SA, Mohtar M, Mohammad SA, Sahdan R, Shaameri Z, Hamzah AS, Mohammat MF: In vitro inhibitory and cytotoxic activity of MFM 501, a novel codonopsinine derivative, against Methicillin-Resistant Staphylococcus aureus clinical isolates. Biomed Res Int. 2015;2015:823829. doi: 10.1155/2015/823829. Epub 2015 Feb 1. [PubMed:25710030 ]
  6. LOTUS database [Link]