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Record Information
Version1.0
Created at2020-12-09 04:29:56 UTC
Updated at2021-07-15 16:58:15 UTC
NP-MRD IDNP0007682
Secondary Accession NumbersNone
Natural Product Identification
Common NameStreptophenazine D
Provided ByNPAtlasNPAtlas Logo
DescriptionStreptophenazine D belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring. Streptophenazine D is found in Streptomyces sp. It was first documented in 2008 (PMID: 18396903). Based on a literature review very few articles have been published on Streptophenazine D (PMID: 28923323).
Structure
Data?1624575149
Synonyms
ValueSource
Methyl 6-(3-hydroxy-1-methoxy-6-methyl-1-oxoheptan-2-yl)phenazine-1-carboxylic acidGenerator
Chemical FormulaC23H26N2O5
Average Mass410.4700 Da
Monoisotopic Mass410.18417 Da
IUPAC Namemethyl 6-[(2R,3S)-3-hydroxy-1-methoxy-6-methyl-1-oxoheptan-2-yl]phenazine-1-carboxylate
Traditional Namemethyl 6-[(2R,3S)-3-hydroxy-1-methoxy-6-methyl-1-oxoheptan-2-yl]phenazine-1-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C(C(O)CCC(C)C)C1=CC=CC2=NC3=C(C=CC=C3N=C12)C(=O)OC
InChI Identifier
InChI=1S/C23H26N2O5/c1-13(2)11-12-18(26)19(23(28)30-4)14-7-5-9-16-20(14)24-17-10-6-8-15(21(17)25-16)22(27)29-3/h5-10,13,18-19,26H,11-12H2,1-4H3
InChI KeyLKJADGCHDSZYKE-UHFFFAOYSA-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 phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentPhenazines and derivatives
Alternative Parents
Substituents
  • Phenazine
  • Beta-hydroxy acid
  • Fatty acid ester
  • Hydroxy acid
  • Pyrazine
  • Benzenoid
  • Fatty acyl
  • Methyl ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
logP3.69ALOGPS
logP4.22ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.51ChemAxon
pKa (Strongest Basic)-0.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area98.61 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity110.3 m³·mol⁻¹ChemAxon
Polarizability44.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA000906
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00040395
Chemspider ID24706803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24879155
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mitova MI, Lang G, Wiese J, Imhoff JF: Subinhibitory concentrations of antibiotics induce phenazine production in a marine Streptomyces sp. J Nat Prod. 2008 May;71(5):824-7. doi: 10.1021/np800032a. Epub 2008 Apr 9. [PubMed:18396903 ]
  2. Zhang X, Chen L, Chai W, Lian XY, Zhang Z: A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP-2216E. Phytochemistry. 2017 Dec;144:119-126. doi: 10.1016/j.phytochem.2017.09.010. Epub 2017 Sep 17. [PubMed:28923323 ]