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Record Information
Version2.0
Created at2022-09-10 05:13:43 UTC
Updated at2022-09-10 05:13:43 UTC
NP-MRD IDNP0295940
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3e)-4-[(1r,4r,6s)-1-hydroxy-2,2,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one
Description(3E)-4-[(1R,4R,6S)-1-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (3e)-4-[(1r,4r,6s)-1-hydroxy-2,2,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one is found in Boscia salicifolia. Based on a literature review very few articles have been published on (3E)-4-[(1R,4R,6S)-1-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H32O8
Average Mass388.4570 Da
Monoisotopic Mass388.20972 Da
IUPAC Name(3E)-4-[(1R,4R,6S)-1-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one
Traditional Name(3E)-4-[(1R,4R,6S)-1-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@H](CC(C)(C)[C@]1(O)\C=C\C(C)=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C19H32O8/c1-10-7-12(8-18(3,4)19(10,25)6-5-11(2)21)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-6,10,12-17,20,22-25H,7-9H2,1-4H3/b6-5+/t10-,12+,13+,14+,15-,16+,17+,19-/m0/s1
InChI KeyISXANBIHUVHPID-OESQVIGSSA-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
Boscia salicifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Ionone derivative
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Cyclohexanol
  • Monosaccharide
  • Oxane
  • Acryloyl-group
  • Cyclic alcohol
  • Enone
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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
logP-0.36ChemAxon
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.62 m³·mol⁻¹ChemAxon
Polarizability40.97 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14564105
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]