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Record Information
Version2.0
Created at2022-09-10 13:45:06 UTC
Updated at2022-09-10 13:45:06 UTC
NP-MRD IDNP0301027
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol
Description(R)-goitrin, also known as ba 51-090278 or epigoitrin, belongs to the class of organic compounds known as oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds (R)-goitrin 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. (5r)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol is found in Brassica napus, Brassica oleracea and Crambe kotschyana. (5r)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol was first documented in 2020 (PMID: 32416341). Based on a literature review very few articles have been published on (R)-goitrin (PMID: 34543684).
Structure
Thumb
Synonyms
ValueSource
(5R)-5-Vinyl-1,3-oxazolidine-2-thioneChEBI
(R)-5-Ethenyl-2-oxazolidinethioneChEBI
(R)-5-Vinyl-2-oxazolidinethioneChEBI
BA 51-090278ChEBI
D-GoitrinChEBI
EpigoitrinChEBI
Chemical FormulaC5H7NOS
Average Mass129.1800 Da
Monoisotopic Mass129.02484 Da
IUPAC Name(5R)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol
Traditional Name(5R)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol
CAS Registry NumberNot Available
SMILES
SC1=NC[C@H](O1)C=C
InChI Identifier
InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m1/s1
InChI KeyUZQVYLOFLQICCT-SCSAIBSYSA-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
Brassica napusLOTUS Database
Brassica oleraceaLOTUS Database
Crambe kotschyanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassOxazolidines
Direct ParentOxazolidines
Alternative Parents
Substituents
  • Thiocarbamic acid ester
  • Oxazolidine
  • Thiocarbamic acid derivative
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP1.73ChemAxon
pKa (Strongest Acidic)6.72ChemAxon
pKa (Strongest Basic)2.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.77 m³·mol⁻¹ChemAxon
Polarizability13.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2297322
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10370
PDB IDNot Available
ChEBI ID183228
Good Scents IDNot Available
References
General References
  1. Chen J, Zhu Z, Gao T, Chen Y, Yang Q, Fu C, Zhu Y, Wang F, Liao W: Isatidis Radix and Isatidis Folium: A systematic review on ethnopharmacology, phytochemistry and pharmacology. J Ethnopharmacol. 2022 Jan 30;283:114648. doi: 10.1016/j.jep.2021.114648. Epub 2021 Sep 20. [PubMed:34543684 ]
  2. Xu Y, Li J, Shi Y, Yang L, Wang Z, Han H, Wang R: Stereoselective pharmacokinetic study of epiprogoitrin and progoitrin in rats with UHPLC-MS/MS method. J Pharm Biomed Anal. 2020 Aug 5;187:113356. doi: 10.1016/j.jpba.2020.113356. Epub 2020 May 7. [PubMed:32416341 ]
  3. LOTUS database [Link]