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Record Information
Version2.0
Created at2020-12-09 06:48:02 UTC
Updated at2021-07-15 17:03:10 UTC
NP-MRD IDNP0009409
Secondary Accession NumbersNone
Natural Product Identification
Common NameLucknolide A
Provided ByNPAtlasNPAtlas Logo
Description(1S,3S,4S,7R,10S,11S)-3,10-dihydroxy-10-(hydroxymethyl)-2,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undec-5-en-8-one belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Lucknolide A is found in Streptomyces sp. Lucknolide A was first documented in 2010 (PMID: 20704312). Based on a literature review very few articles have been published on (1S,3S,4S,7R,10S,11S)-3,10-dihydroxy-10-(hydroxymethyl)-2,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undec-5-en-8-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H12O6
Average Mass228.2000 Da
Monoisotopic Mass228.06339 Da
IUPAC Name(1S,3S,4S,7R,10S,11S)-3,10-dihydroxy-10-(hydroxymethyl)-2,9-dioxatricyclo[5.3.1.0^{4,11}]undec-5-en-8-one
Traditional Name(1S,3S,4S,7R,10S,11S)-3,10-dihydroxy-10-(hydroxymethyl)-2,9-dioxatricyclo[5.3.1.0^{4,11}]undec-5-en-8-one
CAS Registry NumberNot Available
SMILES
OC[C@]1(O)OC(=O)[C@@H]2C=C[C@@H]3[C@@H](O)O[C@H]1[C@H]23
InChI Identifier
InChI=1S/C10H12O6/c11-3-10(14)7-6-4(8(12)15-7)1-2-5(6)9(13)16-10/h1-2,4-8,11-12,14H,3H2/t4-,5+,6-,7-,8-,10-/m0/s1
InChI KeyWFOADYFXGWWIRB-JXVPXHAGSA-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
Streptomyces sp.NPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFuropyrans
Sub ClassNot Available
Direct ParentFuropyrans
Alternative Parents
Substituents
  • Furopyran
  • Delta valerolactone
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Furan
  • Oxolane
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary 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-1.8ALOGPS
logP-1.2ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)10.22ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.64 m³·mol⁻¹ChemAxon
Polarizability20.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA018998
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28288042
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46933683
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yadav PP, Nair V, Dittrich B, Schuffler A, Laatsch H: Lucknolides A and B, tricyclic ketal-lactone metabolites from a terrestrial Streptomyces sp. Org Lett. 2010 Sep 3;12(17):3800-3. doi: 10.1021/ol1014703. [PubMed:20704312 ]