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Record Information
Version1.0
Created at2020-12-09 00:40:09 UTC
Updated at2021-07-15 16:46:20 UTC
NP-MRD IDNP0003400
Secondary Accession NumbersNone
Natural Product Identification
Common NameLuminacin D
Provided ByNPAtlasNPAtlas Logo
Description3-(Butan-2-yl)-5-{2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]Octan-6-yl]-3-methylbutanoyl}-2,6-dihydroxybenzaldehyde belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Luminacin D is found in Streptomyces sp. and Streptomyces sp. Mer-VD1207. It was first documented in 2000 (PMID: 10966073). Based on a literature review very few articles have been published on 3-(butan-2-yl)-5-{2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]Octan-6-yl]-3-methylbutanoyl}-2,6-dihydroxybenzaldehyde.
Structure
Data?1624573810
SynonymsNot Available
Chemical FormulaC24H34O8
Average Mass450.5280 Da
Monoisotopic Mass450.22537 Da
IUPAC Name3-[(2R)-butan-2-yl]-5-[(2S)-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutanoyl]-2,6-dihydroxybenzaldehyde
Traditional Name3-[(2R)-butan-2-yl]-5-[(2S)-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutanoyl]-2,6-dihydroxybenzaldehyde
CAS Registry NumberNot Available
SMILES
CCC(C)C1=C(O)C(C=O)=C(O)C(=C1)C(=O)C(C(C)C)[C@H]1C[C@@H](O)[C@@]2(O[C@H]2CC)[C@H](O)O1
InChI Identifier
InChI=1S/C24H34O8/c1-6-12(5)13-8-14(21(28)15(10-25)20(13)27)22(29)19(11(3)4)16-9-17(26)24(23(30)31-16)18(7-2)32-24/h8,10-12,16-19,23,26-28,30H,6-7,9H2,1-5H3/t12?,16-,17-,18+,19?,23-,24+/m1/s1
InChI KeyKJXVOXDWWAXZJY-QLYMQFIGSA-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
Streptomyces sp. Mer-VD1207Bacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Phenylpropane
  • Hydroxybenzaldehyde
  • Benzaldehyde
  • Benzoyl
  • Resorcinol
  • Aryl alkyl ketone
  • Phenol
  • Aryl-aldehyde
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Hemiacetal
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP2.81ALOGPS
logP5.27ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.31ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity117.81 m³·mol⁻¹ChemAxon
Polarizability48.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA004441
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78436759
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139584321
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Naruse N, Kageyama-Kawase R, Funahashi Y, Wakabayashi T: Luminacins: a family of capillary tube formation inhibitors from Streptomyces sp. I. Taxomony, fermentation, isolation, physico-chemical properties and structure elucidation. J Antibiot (Tokyo). 2000 Jun;53(6):579-90. doi: 10.7164/antibiotics.53.579. [PubMed:10966073 ]