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Record Information
Version2.0
Created at2022-09-01 21:50:48 UTC
Updated at2022-09-01 21:50:48 UTC
NP-MRD IDNP0143153
Secondary Accession NumbersNone
Natural Product Identification
Common Name(8s)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0¹,¹¹.0²,⁷]pentadeca-9,11-dien-13-one
DescriptionPhyllanthine belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. (8s)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0¹,¹¹.0²,⁷]pentadeca-9,11-dien-13-one is found in Margaritaria indica, Phyllanthus amarus and Phyllanthus niruri. (8s)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0¹,¹¹.0²,⁷]pentadeca-9,11-dien-13-one was first documented in 1984 (PMID: 17340265). Based on a literature review a small amount of articles have been published on Phyllanthine (PMID: 11052071) (PMID: 10649387).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H17NO3
Average Mass247.2940 Da
Monoisotopic Mass247.12084 Da
IUPAC Name(8S)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadeca-9,11-dien-13-one
Traditional Name(8S)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadeca-9,11-dien-13-one
CAS Registry NumberNot Available
SMILES
COC1CCN2[C@H]3CC4(OC(=O)C=C4C=C3)C2C1
InChI Identifier
InChI=1S/C14H17NO3/c1-17-11-4-5-15-10-3-2-9-6-13(16)18-14(9,8-10)12(15)7-11/h2-3,6,10-12H,4-5,7-8H2,1H3/t10-,11?,12?,14?/m1/s1
InChI KeyYKLWRYOORWTCQQ-YAJDGLSUSA-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
Margaritaria indicaLOTUS Database
Phyllanthus amarusLOTUS Database
Phyllanthus niruriLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndolizidines
Sub ClassNot Available
Direct ParentIndolizidines
Alternative Parents
Substituents
  • Indolizidine
  • Azepine
  • N-alkylpyrrolidine
  • Piperidine
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Pyrrolidine
  • Dihydrofuran
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactone
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • 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
logP1.1ALOGPS
logP0.52ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.65 m³·mol⁻¹ChemAxon
Polarizability25.8 ųChemAxon
Number of Rings4ChemAxon
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 IDC00038277
Chemspider ID32819287
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122236592
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Han G, LaPorte MG, Folmer JJ, Werner KM, Weinreb SM: Total syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (-)-norsecurinine, and phyllanthine. J Org Chem. 2000 Oct 6;65(20):6293-306. doi: 10.1021/jo000260z. [PubMed:11052071 ]
  2. Han G, LaPorte MG, Folmer JJ, Werner KM, Weinreb SM: A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (-)-Norsecurinine and Phyllanthine. Angew Chem Int Ed Engl. 2000 Jan;39(1):237-240. doi: 10.1002/(sici)1521-3773(20000103)39:1<237::aid-anie237>3.0.co;2-b. [PubMed:10649387 ]
  3. Mulchandani NB, Hassarajani SA: 4-Methoxy-nor-Securinine, a New Alkaloid from Phyllanthus niruri. Planta Med. 1984 Feb;50(1):104-5. doi: 10.1055/s-2007-969635. [PubMed:17340265 ]
  4. LOTUS database [Link]