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Record Information
Version1.0
Created at2022-09-07 19:32:16 UTC
Updated at2022-09-07 19:32:16 UTC
NP-MRD IDNP0255146
Secondary Accession NumbersNone
Natural Product Identification
Common Nameparomomycin ii
DescriptionNeomycin F belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions. Neomycin F is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. paromomycin ii is found in Streptomyces fradiae. It was first documented in 2020 (PMID: 33320045). Based on a literature review a significant number of articles have been published on Neomycin F (PMID: 34313097) (PMID: 33134875) (PMID: 33091215) (PMID: 32586265).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H45N5O14
Average Mass615.6340 Da
Monoisotopic Mass615.29630 Da
IUPAC Name(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol
Traditional Name(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol
CAS Registry NumberNot Available
SMILES
NC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7-,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChI KeyUOZODPSAJZTQNH-VZXHOKRSSA-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 fradiaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent4,5-disubstituted 2-deoxystreptamines
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Cyclitol or derivatives
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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
logP-8.3ChemAxon
pKa (Strongest Acidic)12.23ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area347.32 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity134.24 m³·mol⁻¹ChemAxon
Polarizability60.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2303594
KEGG Compound IDC17712
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3040200
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sahan Yapicier O, Sababoglu E, Ozturk D, Turutoglu H, Pehlivanoglu F, Kaya M: Lancefield classification and antimicrobial resistance of hemolytic streptococci isolated from bovine mastitis. Vet Ital. 2021 May 11;57(1):41-47. doi: 10.12834/VetIt.1855.9879.3. [PubMed:34313097 ]
  2. Namsi A, Rabaoui A, Masiello M, Moretti A, Othmani A, Gargouri S, Gdoura R, Werbrouck SPO: First report of Leaf Wilt caused by Fusarium proliferatum and F. brachygibbosum on Date Palm (Phoenix dactylifera) in Tunisia. Plant Dis. 2020 Dec 15. doi: 10.1094/PDIS-08-20-1791-PDN. [PubMed:33320045 ]
  3. Park S, Lee JW, Jerez Bogota K, Francis D, Gonzalez-Vega JC, Htoo JK, Woyengo TA: Growth performance and gut health of Escherichia coli-challenged weaned pigs fed diets supplemented with a Bacillus subtilis direct-fed microbial. Transl Anim Sci. 2020 Sep 12;4(3):txaa172. doi: 10.1093/tas/txaa172. eCollection 2020 Jul. [PubMed:33134875 ]
  4. Kaczorek-Lukowska E, Sowinska P, Franaszek A, Dziewulska D, Malaczewska J, Stenzel T: Can domestic pigeon be a potential carrier of zoonotic Salmonella? Transbound Emerg Dis. 2021 Jul;68(4):2321-2333. doi: 10.1111/tbed.13891. Epub 2020 Nov 4. [PubMed:33091215 ]
  5. Yao H, Fan C, Lu Y, Fan X, Xia L, Li P, Wang R, Tang T, Wang Y, Qi K: Alteration of gut microbiota affects expression of adiponectin and resistin through modifying DNA methylation in high-fat diet-induced obese mice. Genes Nutr. 2020 Jun 26;15(1):12. doi: 10.1186/s12263-020-00671-3. [PubMed:32586265 ]
  6. LOTUS database [Link]