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Record Information
Version2.0
Created at2022-04-28 10:04:01 UTC
Updated at2022-04-28 10:04:01 UTC
NP-MRD IDNP0065869
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3S,5R,6S)-5,6-Epoxy-5,6,7,8-tetrahydro-3-hydroxy-8-oxo-10'-apo-beta,psi-carotenal
Description(2E,4E,6E,8E,10E,12E)-15-[(1S,4S,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]Heptan-1-yl]-4,9,13-trimethyl-14-oxopentadeca-2,4,6,8,10,12-hexaenal belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (3S,5R,6S)-5,6-Epoxy-5,6,7,8-tetrahydro-3-hydroxy-8-oxo-10'-apo-beta,psi-carotenal is found in Phaeodactylum tricornutum. Based on a literature review very few articles have been published on (2E,4E,6E,8E,10E,12E)-15-[(1S,4S,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]Heptan-1-yl]-4,9,13-trimethyl-14-oxopentadeca-2,4,6,8,10,12-hexaenal.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H36O4
Average Mass424.5810 Da
Monoisotopic Mass424.26136 Da
IUPAC Name(2E,4E,6E,8E,10E,12E)-15-[(1S,4S,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-4,9,13-trimethyl-14-oxopentadeca-2,4,6,8,10,12-hexaenal
Traditional Name(2E,4E,6E,8E,10E,12E)-15-[(1S,4S,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-4,9,13-trimethyl-14-oxopentadeca-2,4,6,8,10,12-hexaenal
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)C[C@@]12O[C@@]1(C)C[C@@H](O)CC2(C)C
InChI Identifier
InChI=1S/C27H36O4/c1-20(11-7-8-12-21(2)14-10-16-28)13-9-15-22(3)24(30)19-27-25(4,5)17-23(29)18-26(27,6)31-27/h7-16,23,29H,17-19H2,1-6H3/b8-7+,13-9+,14-10+,20-11+,21-12+,22-15+/t23-,26-,27-/m0/s1
InChI KeyHQQUWEPSOVTLND-OTEXYFMMSA-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
Phaeodactylum tricornutumChromalveolata
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Oxepane
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Alpha,beta-unsaturated ketone
  • Enone
  • Enal
  • Cyclic alcohol
  • Alpha,beta-unsaturated aldehyde
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • 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
logP5.41ALOGPS
logP4.44ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)15.09ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity132.04 m³·mol⁻¹ChemAxon
Polarizability50.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 Compound162972644
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available