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Record Information
Version1.0
Created at2020-12-09 03:27:37 UTC
Updated at2021-07-15 16:54:49 UTC
NP-MRD IDNP0006448
Secondary Accession NumbersNone
Natural Product Identification
Common NameTAN-950 A
Provided ByNPAtlasNPAtlas Logo
Description3-(5-Oxoisoxazolin-4-yl)-L-alanine zwitterion is also known as beta-(isoxazolin-5-on-4-yl)-L-alanine. TAN-950 A is found in Streptomyces platensis A-136 (IFO 14603 FERM BP-1786) and Streptomyces sp.. It was first documented in 1991 (PMID: 1680709). Based on a literature review very few articles have been published on 3-(5-oxoisoxazolin-4-yl)-L-alanine zwitterion (PMID: 8889043) (PMID: 34380192) (PMID: 34380191) (PMID: 34380190).
Structure
Data?1624574715
Synonyms
ValueSource
3-(5-Oxoisoxazolin-4-yl)-L-alanineChEBI
beta-(Isoxazolin-5-on-4-yl)-L-alanineChEBI
b-(Isoxazolin-5-on-4-yl)-L-alanineGenerator
Β-(isoxazolin-5-on-4-yl)-L-alanineGenerator
2-Amino-3-(2,5-dihydro-5-oxo-4-isoxazolyl)propanoic acidMeSH
TAN-950aMeSH
Tan 950 aMeSH
Chemical FormulaC6H8N2O4
Average Mass172.1400 Da
Monoisotopic Mass172.04841 Da
IUPAC Name(2S)-2-amino-3-(5-oxo-2,5-dihydro-1,2-oxazol-4-yl)propanoic acid
Traditional Name(2S)-2-amino-3-(5-oxo-2H-1,2-oxazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CC1=CNOC1=O)C(O)=O
InChI Identifier
InChI=1S/C6H8N2O4/c7-4(5(9)10)1-3-2-8-12-6(3)11/h2,4,8H,1,7H2,(H,9,10)/t4-/m0/s1
InChI KeyLVNJBTYSYFSYFG-BYPYZUCNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces platensis A-136 (IFO 14603 FERM BP-1786)Bacteria
Streptomyces sp.NPAtlas
Chemical Taxonomy
ClassificationNot classified
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-2.8ALOGPS
logP-3.4ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.65 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.07 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA003782
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8351825
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10176320
PDB IDNot Available
ChEBI ID76856
Good Scents IDNot Available
References
General References
  1. Iwama T, Nagai Y, Tamura N, Harada S, Nagaoka A: A novel glutamate agonist, TAN-950 A, isolated from streptomycetes. Eur J Pharmacol. 1991 May 17;197(2-3):187-92. doi: 10.1016/0014-2999(91)90520-z. [PubMed:1680709 ]
  2. Ikegami F, Kamiya M, Kuo YH, Lambein F, Murakoshi I: Enzymatic synthesis of two isoxazolylalanine isomers by cysteine synthases in Lathyrus species. Biol Pharm Bull. 1996 Sep;19(9):1214-5. doi: 10.1248/bpb.19.1214. [PubMed:8889043 ]
  3. Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
  4. Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
  5. Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]