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Record Information
Version2.0
Created at2024-03-21 17:32:58 UTC
Updated at2025-12-21 21:41:03 UTC
NP-MRD IDNP0332707
Natural Product DOIhttps://doi.org/10.57994/1967
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenazinolin D
DescriptionPhenazinolin 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. phenazinolin D was first documented in 2023 (PMID: 37463274). Based on a literature review a small amount of articles have been published on phenazinolin D (PMID: 38517947) (PMID: 36640042).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H16N4O6
Average Mass468.4250 Da
Monoisotopic Mass468.10698 Da
IUPAC Name(1R,17S,29S)-6,21,29-trihydroxy-16-oxa-4,11,19,26-tetraazaheptacyclo[15.11.1.0^{2,15}.0^{3,12}.0^{5,10}.0^{18,27}.0^{20,25}]nonacosa-2,4,6,8,10,12,14,18,20(25),21,23,26-dodecaene-13-carboxylic acid
Traditional Name(1R,17S,29S)-6,21,29-trihydroxy-16-oxa-4,11,19,26-tetraazaheptacyclo[15.11.1.0^{2,15}.0^{3,12}.0^{5,10}.0^{18,27}.0^{20,25}]nonacosa-2,4,6,8,10,12,14,18,20(25),21,23,26-dodecaene-13-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@@H]2CC3=NC4=C(N=C3[C@@H]1OC1=CC(C(O)=O)=C3N=C5C=CC=C(O)C5=NC3=C21)C(O)=CC=C4
InChI Identifier
InChI=1S/C25H16N4O6/c30-14-5-1-3-11-19(14)28-21-13(26-11)7-9-17-16(35-24(21)23(9)32)8-10(25(33)34)18-22(17)29-20-12(27-18)4-2-6-15(20)31/h1-6,8-9,23-24,30-32H,7H2,(H,33,34)/t9-,23+,24+/m1/s1
InChI KeyQKUOMBQMSVMPAK-ILWJZNQRSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)[email protected]The University of QueenslandSarani Kankanamge2024-03-21View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)[email protected]The University of QueenslandSarani Kankanamge2024-03-21View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)[email protected]The University of QueenslandSarani Kankanamge2024-03-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)[email protected]The University of QueenslandSarani Kankanamge2024-03-21View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces virginiae
      Not Available
Chemical Taxonomy
DescriptionThis compound 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
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Quinonimine
  • O-quinonimine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Heterocyclic fatty acid
  • Branched fatty acid
  • Alkyl aryl ether
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Pyrazine
  • Oxane
  • Heteroaromatic compound
  • Secondary ketimine
  • Cyclic alcohol
  • Secondary alcohol
  • Ketimine
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Alcohol
  • 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
logP2.41ChemAxon
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)2.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity118.02 m³·mol⁻¹ChemAxon
Polarizability26.42 ųChemAxon
Number of Rings7ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kankanamge S, Khalil ZG, Capon RJ: Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091. J Nat Prod. 2024 Apr 26;87(4):1084-1091. doi: 10.1021/acs.jnatprod.4c00042. Epub 2024 Mar 22. [PubMed:38517947 ]
  2. Zhuang Y, Yang F, Menon A, Song JM, Espinoza RV, Schultz PJ, Garner AL, Tripathi A: An ECD and NMR/DP4+ Computational Pipeline for Structure Revision and Elucidation of Diphenazine-Based Natural Products. J Nat Prod. 2023 Jul 28;86(7):1801-1814. doi: 10.1021/acs.jnatprod.3c00306. Epub 2023 Jul 18. [PubMed:37463274 ]
  3. Huang Z, Tang W, Jiang T, Xu X, Kong K, Shi S, Zhang S, Cao W, Zhang Y: Structural characterization, derivatization and antibacterial activity of secondary metabolites produced by termite-associated Streptomyces showdoensis BYF17. Pest Manag Sci. 2023 May;79(5):1800-1808. doi: 10.1002/ps.7359. Epub 2023 Jan 25. [PubMed:36640042 ]
  4. DOI: 10.1021/acs.jnatprod.4c00042
  5. PMID: 38517947