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Record Information
Version1.0
Created at2022-09-05 23:25:26 UTC
Updated at2022-09-05 23:25:26 UTC
NP-MRD IDNP0221764
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid
DescriptionUK-3A, also known as uk 3A, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. UK-3A 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. It was first documented in 1997 (PMID: 9510913). Based on a literature review a small amount of articles have been published on UK-3A (PMID: 9711246) (PMID: 20621723).
Structure
Thumb
Synonyms
ValueSource
(3S,6S,7R,8R)-8-Benzyl-3-{[(3-hydroxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoateChEBI
(3S,6S,7R,8R)-8-Benzyl-3-{[(3-hydroxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoic acidGenerator
UK 3aMeSH
Chemical FormulaC25H28N2O8
Average Mass484.5050 Da
Monoisotopic Mass484.18457 Da
IUPAC NameN-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid
Traditional NameN-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@H](COC(=O)[C@@H]1CC1=CC=CC=C1)N=C(O)C1=NC=CC=C1O
InChI Identifier
InChI=1S/C25H28N2O8/c1-14(2)23(30)35-21-15(3)34-25(32)18(27-22(29)20-19(28)10-7-11-26-20)13-33-24(31)17(21)12-16-8-5-4-6-9-16/h4-11,14-15,17-18,21,28H,12-13H2,1-3H3,(H,27,29)/t15-,17+,18-,21-/m0/s1
InChI KeyLATFDMCUVSRKNK-DKXUYOFUSA-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 n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Tricarboxylic acid or derivatives
  • 2-heteroaryl carboxamide
  • Hydroxypyridine
  • Monocyclic benzene moiety
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Lactone
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen 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
logP4.5ChemAxon
pKa (Strongest Acidic)5.94ChemAxon
pKa (Strongest Basic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area144.61 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity122.19 m³·mol⁻¹ChemAxon
Polarizability48.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID416802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound474760
PDB IDNot Available
ChEBI ID66341
Good Scents IDNot Available
References
General References
  1. Ueki M, Kusumoto A, Hanafi M, Shibata K, Tanaka T, Taniguchi M: UK-3A, a novel antifungal antibiotic from Streptomyces sp. 517-02: fermentation, isolation, structural elucidation and biological properties. J Antibiot (Tokyo). 1997 Jul;50(7):551-5. doi: 10.7164/antibiotics.50.551. [PubMed:9711246 ]
  2. Arsianti A, Hanafi M, Saepudin E, Morimoto T, Kakiuchi K: Synthesis and biological activity of 2-hydroxynicotinoyl-serine-butyl esters related to antibiotic UK-3A. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4018-20. doi: 10.1016/j.bmcl.2010.05.104. Epub 2010 Jun 2. [PubMed:20621723 ]
  3. Ueki M, Taniguchi M: The mode of action of UK-2A and UK-3A, novel antifungal antibiotics from Streptomyces sp. 517-02. J Antibiot (Tokyo). 1997 Dec;50(12):1052-7. doi: 10.7164/antibiotics.50.1052. [PubMed:9510913 ]
  4. LOTUS database [Link]