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Record Information
Version1.0
Created at2022-09-04 03:55:50 UTC
Updated at2022-09-04 03:55:50 UTC
NP-MRD IDNP0187709
Secondary Accession NumbersNone
Natural Product Identification
Common Name{[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
Description2-{[2-Amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[5-(4-formyl-2-hydroxy-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. {[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid is found in Streptomyces tendae. 2-{[2-Amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[5-(4-formyl-2-hydroxy-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2-{[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[5-(4-formyl-2-hydroxy-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetateGenerator
Chemical FormulaC21H26N4O10
Average Mass494.4570 Da
Monoisotopic Mass494.16489 Da
IUPAC Name2-[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido]-2-[5-(4-formyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
Traditional Name[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido][5-(4-formyl-2-oxo-3H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CC(C(N)C(=O)NC(C1OC(C(O)C1O)N1C=C(NC1=O)C=O)C(O)=O)C(O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C21H26N4O10/c1-8(14(28)9-2-4-11(27)5-3-9)12(22)18(31)24-13(20(32)33)17-15(29)16(30)19(35-17)25-6-10(7-26)23-21(25)34/h2-8,12-17,19,27-30H,22H2,1H3,(H,23,34)(H,24,31)(H,32,33)
InChI KeyOYYBZOZCMOFKEF-UHFFFAOYSA-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 tendaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP-0.37ALOGPS
logP-4.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)7.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area231.98 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.19 m³·mol⁻¹ChemAxon
Polarizability46.74 ųChemAxon
Number of Rings3ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13856301
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]