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Record Information
Version2.0
Created at2021-06-21 00:24:40 UTC
Updated at2021-06-30 00:18:11 UTC
NP-MRD IDNP0042846
Secondary Accession NumbersNone
Natural Product Identification
Common Nametuberostemoline B
Provided ByJEOL DatabaseJEOL Logo
DescriptionTuberostemoline B belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. tuberostemoline B is found in Stemona tuberosa. tuberostemoline B was first documented in 2014 (Gao, Y., et al.). Based on a literature review very few articles have been published on Tuberostemoline B.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H25NO5
Average Mass323.3890 Da
Monoisotopic Mass323.17327 Da
IUPAC Name(1S,4R,5S,6R,7S)-7-ethyl-6-hydroxy-4-methyl-2-oxa-13-azatricyclo[11.2.1.0^{1,5}]hexadecane-3,8,16-trione
Traditional Name(1S,4R,5S,6R,7S)-7-ethyl-6-hydroxy-4-methyl-2-oxa-13-azatricyclo[11.2.1.0^{1,5}]hexadecane-3,8,16-trione
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])[C@]2([H])[C@]([H])(C(=O)O[C@]22C(=O)N(C([H])([H])C2([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)[C@@]1([H])C([H])([H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C17H25NO5/c1-3-11-12(19)6-4-5-8-18-9-7-17(16(18)22)13(14(11)20)10(2)15(21)23-17/h10-11,13-14,20H,3-9H2,1-2H3/t10-,11-,13+,14+,17+/m1/s1
InChI KeyVZKGMGRBYGXXIX-RTDVULAYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Stemona tuberosaJEOL database
    • Gao, Y., et al. J. Tetrahedron 70, 967 (2014)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Oxolane
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Cyclic ketone
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactam
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • 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
logP0.91ALOGPS
logP0.72ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.91 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.17 m³·mol⁻¹ChemAxon
Polarizability33.15 ųChemAxon
Number of Rings3ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102126218
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Gao, Y., et al. (2014). Gao, Y., et al. J. Tetrahedron 70, 967 (2014). J. Tetrahedron.