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Record Information
Version2.0
Created at2022-09-03 21:30:23 UTC
Updated at2022-09-03 21:30:23 UTC
NP-MRD IDNP0182726
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3z,6z)-3-(2-methylpropylidene)-6-(phenylmethylidene)pyrazine-2,5-diol
DescriptionAlbonoursin belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Albonoursin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3z,6z)-3-(2-methylpropylidene)-6-(phenylmethylidene)pyrazine-2,5-diol was first documented in 2009 (PMID: 19430487). Based on a literature review a small amount of articles have been published on albonoursin (PMID: 30901830) (PMID: 35722152) (PMID: 31175189) (PMID: 25048158).
Structure
Thumb
Synonyms
ValueSource
3-Benzylidene-6-isobutylidene-2,5-dioxopiperazineChEBI
Cyclo(dehydroleucyl-dehydrophenylalanyl)ChEBI
Cyclo(dehydrophenylalanyl-dehydroleucyl)ChEBI
Cyclo(deltaleu-deltaphe)ChEBI
Cyclo(deltaphe-deltaleu)ChEBI
(3Z,6Z)-3-Benzylidene-6-(2-methylpropylidene)piperazine-2,5-dioneKegg
Chemical FormulaC15H16N2O2
Average Mass256.3050 Da
Monoisotopic Mass256.12118 Da
IUPAC Name(3Z,6Z)-3-(2-methylpropylidene)-6-(phenylmethylidene)-3,6-dihydropyrazine-2,5-diol
Traditional Name(3Z,6Z)-3-(2-methylpropylidene)-6-(phenylmethylidene)pyrazine-2,5-diol
CAS Registry NumberNot Available
SMILES
CC(C)\C=C1/N=C(O)\C(=C\C2=CC=CC=C2)\N=C1O
InChI Identifier
InChI=1S/C15H16N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-10H,1-2H3,(H,16,19)(H,17,18)/b12-8-,13-9-
InChI KeyLCIIOYPBHIZBOD-JMVBYTIWSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Benzenoid
  • Pyrazine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP3.74ChemAxon
pKa (Strongest Acidic)5.63ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.18 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.07 m³·mol⁻¹ChemAxon
Polarizability28.32 ųChemAxon
Number of Rings2ChemAxon
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 ID4812367
KEGG Compound IDC20520
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6109346
PDB IDNot Available
ChEBI ID71609
Good Scents IDNot Available
References
General References
  1. Xu X, Han J, Lin R, Polyak SW, Song F: Two New Piperazine-Triones from a Marine-Derived Streptomycetes sp. Strain SMS636. Mar Drugs. 2019 Mar 21;17(3). pii: md17030186. doi: 10.3390/md17030186. [PubMed:30901830 ]
  2. Gondry M, Sauguet L, Belin P, Thai R, Amouroux R, Tellier C, Tuphile K, Jacquet M, Braud S, Courcon M, Masson C, Dubois S, Lautru S, Lecoq A, Hashimoto S, Genet R, Pernodet JL: Cyclodipeptide synthases are a family of tRNA-dependent peptide bond-forming enzymes. Nat Chem Biol. 2009 Jun;5(6):414-20. doi: 10.1038/nchembio.175. [PubMed:19430487 ]
  3. Saleem S, Bibi S, Yousafi Q, Hassan T, Khan MS, Hasan MM, Chopra H, Moustafa M, Al-Shehri M, Khalid M, Kabra A: Identification of Effective and Nonpromiscuous Antidiabetic Drug Molecules from Penicillium Species. Evid Based Complement Alternat Med. 2022 Jun 8;2022:7040547. doi: 10.1155/2022/7040547. eCollection 2022. [PubMed:35722152 ]
  4. Aubry C, Pernodet JL, Lautru S: Modular and Integrative Vectors for Synthetic Biology Applications in Streptomyces spp. Appl Environ Microbiol. 2019 Aug 1;85(16):e00485-19. doi: 10.1128/AEM.00485-19. Print 2019 Aug 15. [PubMed:31175189 ]
  5. Li Y, Lai YM, Lu Y, Yang YL, Chen S: Analysis of the biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba. Arch Microbiol. 2014 Nov;196(11):765-74. doi: 10.1007/s00203-014-1015-x. Epub 2014 Jul 22. [PubMed:25048158 ]
  6. LOTUS database [Link]