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Record Information
Version2.0
Created at2022-09-12 12:37:43 UTC
Updated at2022-09-12 12:37:43 UTC
NP-MRD IDNP0328815
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3s,4s,5e,7s)-7-butoxy-3-hydroxy-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione
DescriptionCHEMBL518881 belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. (1r,3s,4s,5e,7s)-7-butoxy-3-hydroxy-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione is found in Penicillium chrysogenum. Based on a literature review very few articles have been published on CHEMBL518881.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H28O5
Average Mass348.4390 Da
Monoisotopic Mass348.19367 Da
IUPAC Name(1R,3S,4S,5E,7S)-7-butoxy-3-hydroxy-5-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione
Traditional Name(1R,3S,4S,5E,7S)-7-butoxy-3-hydroxy-5-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione
CAS Registry NumberNot Available
SMILES
CCCCO[C@H]1C[C@H]2\C(=C(/O)\C=C\C=C\C)C(=O)[C@]1(C)C(=O)[C@@]2(C)O
InChI Identifier
InChI=1S/C20H28O5/c1-5-7-9-10-14(21)16-13-12-15(25-11-8-6-2)19(3,17(16)22)18(23)20(13,4)24/h5,7,9-10,13,15,21,24H,6,8,11-12H2,1-4H3/b7-5+,10-9+,16-14+/t13-,15-,19+,20-/m0/s1
InChI KeySSIULBZZANASKU-JMHWJZGWSA-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
Penicillium chrysogenumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAcyloins
Alternative Parents
Substituents
  • Acyloin
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Ether
  • Enol
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.34ChemAxon
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.61 m³·mol⁻¹ChemAxon
Polarizability38.59 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 ID24717906
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44584010
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]