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Record Information
Version2.0
Created at2022-09-05 17:21:09 UTC
Updated at2022-09-05 17:21:09 UTC
NP-MRD IDNP0217118
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione
DescriptionIsoprekinamycin belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. 1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione is found in Streptomyces murayamaensis. 1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione was first documented in 2007 (PMID: 17585773). Based on a literature review a small amount of articles have been published on Isoprekinamycin (PMID: 30656941) (PMID: 30465587) (PMID: 28044443) (PMID: 21048414).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H10N2O4
Average Mass318.2880 Da
Monoisotopic Mass318.06406 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=C2C3=C(C4=C(O)C=CC=C4C3=O)C(=O)C(=[N+]=[N-])C2=C1
InChI Identifier
InChI=1S/C18H10N2O4/c1-7-5-9-13(11(22)6-7)14-15(18(24)16(9)20-19)12-8(17(14)23)3-2-4-10(12)21/h2-6,21-22H,1H3
InChI KeyOWPHUUBRUYFHMJ-UHFFFAOYSA-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
Streptomyces murayamaensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Fluorene
  • 1-naphthol
  • Naphthalene
  • Aryl ketone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Diazo compound
  • Organic diazonium salt
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28284299
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16748289
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tang SQ, Bricard J, Schmitt M, Bihel F: Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP. Org Lett. 2019 Feb 1;21(3):844-848. doi: 10.1021/acs.orglett.9b00031. Epub 2019 Jan 18. [PubMed:30656941 ]
  2. Guo J, Peng X, Wang X, Xie F, Zhang X, Liang G, Sun Z, Liu Y, Cheng M, Liu Y: A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes. Org Biomol Chem. 2018 Dec 5;16(47):9147-9151. doi: 10.1039/c8ob02582g. [PubMed:30465587 ]
  3. Kawamura M, Kamo S, Azuma S, Kubo K, Sasamori T, Tokitoh N, Kuramochi K, Tsubaki K: Skeletal Rearrangements of Polycyclic alpha-Ketols. Org Lett. 2017 Jan 20;19(2):301-303. doi: 10.1021/acs.orglett.6b03541. Epub 2017 Jan 3. [PubMed:28044443 ]
  4. Kumamoto T: [Synthetic studies on kinamycin antibiotics]. Yakugaku Zasshi. 2010 Nov;130(11):1535-41. doi: 10.1248/yakushi.130.1535. [PubMed:21048414 ]
  5. Liu W, Buck M, Chen N, Shang M, Taylor NJ, Asoud J, Wu X, Hasinoff BB, Dmitrienko GI: Total synthesis of isoprekinamycin: structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells. Org Lett. 2007 Jul 19;9(15):2915-8. doi: 10.1021/ol0712374. Epub 2007 Jun 22. [PubMed:17585773 ]
  6. LOTUS database [Link]