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Record Information
Version1.0
Created at2022-09-05 21:16:11 UTC
Updated at2022-09-05 21:16:12 UTC
NP-MRD IDNP0220065
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4r,5e,7s,10s)-4,7-dihydroxy-10-nonyl-3,4,7,8,9,10-hexahydrooxecin-2-one
DescriptionSeimatopolide B belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. (4r,5e,7s,10s)-4,7-dihydroxy-10-nonyl-3,4,7,8,9,10-hexahydrooxecin-2-one is found in Seimatosporium discosioides. It was first documented in 2013 (PMID: 23563244). Based on a literature review very few articles have been published on Seimatopolide B.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H32O4
Average Mass312.4500 Da
Monoisotopic Mass312.23006 Da
IUPAC Name(4R,7S,10S)-4,7-dihydroxy-10-nonyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-one
Traditional Name(4R,7S,10S)-4,7-dihydroxy-10-nonyl-3,4,7,8,9,10-hexahydrooxecin-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCC[C@H]1CC[C@H](O)\C=C\[C@H](O)CC(=O)O1
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-9-17-13-12-15(19)10-11-16(20)14-18(21)22-17/h10-11,15-17,19-20H,2-9,12-14H2,1H3/b11-10+/t15-,16+,17+/m1/s1
InChI KeyXPIVIEHYRXZHSQ-SRXSTOJXSA-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
Seimatosporium discosioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxocins
Sub ClassNot Available
Direct ParentOxocins
Alternative Parents
Substituents
  • Oxocin
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP3.76ChemAxon
pKa (Strongest Acidic)14.44ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.46 m³·mol⁻¹ChemAxon
Polarizability37.28 ųChemAxon
Number of Rings1ChemAxon
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 ID28522727
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57409556
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Reddy CR, Dilipkumar U, Reddy MD, Rao NN: Total synthesis and revision of the absolute configuration of seimatopolide B. Org Biomol Chem. 2013 May 28;11(20):3355-64. doi: 10.1039/c3ob27518c. [PubMed:23563244 ]
  2. LOTUS database [Link]