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Record Information
Version2.0
Created at2020-12-09 01:40:39 UTC
Updated at2021-07-15 16:48:29 UTC
NP-MRD IDNP0004185
Secondary Accession NumbersNone
Natural Product Identification
Common NameParasitenone
Provided ByNPAtlasNPAtlas Logo
Description(1S,5S,6S)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]Hept-3-en-2-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Parasitenone is found in Aspergillus parasiticus. Parasitenone was first documented in 2002 (PMID: 12027772). Based on a literature review very few articles have been published on (1S,5S,6S)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]Hept-3-en-2-one.
Structure
Data?1624574035
SynonymsNot Available
Chemical FormulaC7H8O4
Average Mass156.1370 Da
Monoisotopic Mass156.04226 Da
IUPAC Name(1S,5S,6S)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
Traditional Name(1S,5S,6S)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
CAS Registry NumberNot Available
SMILES
OCC1=CC(=O)[C@H]2O[C@H]2[C@H]1O
InChI Identifier
InChI=1S/C7H8O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,5-8,10H,2H2/t5-,6+,7-/m0/s1
InChI KeyRZGZRGXCPXHJFW-XVMARJQXSA-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
Aspergillus parasiticusNPAtlas
Species Where Detected
Species NameSourceReference
Ascochyta chrysanthemiKNApSAcK Database
Mycosphaerella ligulicolaKNApSAcK Database
Penicillium claviformeKNApSAcK Database
Penicillium griseofulvumKNApSAcK Database
Phoma chrysanthemiKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • 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
logP-1.5ALOGPS
logP-1.3ChemAxon
logS0.44ALOGPS
pKa (Strongest Acidic)13.25ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.95 m³·mol⁻¹ChemAxon
Polarizability14.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA019119
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID552488
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound636767
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Son BW, Choi JS, Kim JC, Nam KW, Kim DS, Chung HY, Kang JS, Choi HD: Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus. J Nat Prod. 2002 May;65(5):794-5. doi: 10.1021/np010450k. [PubMed:12027772 ]