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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:57:07 UTC
Update Date2023-02-21 17:28:37 UTC
HMDB IDHMDB0041280
Secondary Accession Numbers
  • HMDB41280
Metabolite Identification
Common NameRaphanusamic acid
DescriptionRaphanusamic acid, also known as raphanusamate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Raphanusamic acid has been detected, but not quantified in, brassicas. This could make raphanusamic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Raphanusamic acid.
Structure
Data?1677000516
Synonyms
ValueSource
RaphanusamateGenerator
(4R)-(-)-2-thioxo-4-Thiazolidinecarboxylic acidHMDB
(R)-(-)-2-thioxo-4-Thiazolidinecarboxylic acidHMDB
2-Sulfanyl-4,5-dihydro-1,3-thiazole-4-carboxylateGenerator
2-Sulphanyl-4,5-dihydro-1,3-thiazole-4-carboxylateGenerator
2-Sulphanyl-4,5-dihydro-1,3-thiazole-4-carboxylic acidGenerator
Chemical FormulaC4H5NO2S2
Average Molecular Weight163.218
Monoisotopic Molecular Weight162.976169789
IUPAC Name2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid
Traditional Name2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid
CAS Registry Number98169-56-3
SMILES
OC(=O)C1CSC(=S)N1
InChI Identifier
InChI=1S/C4H5NO2S2/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)
InChI KeySQUOCHQOQMZGQP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Thiazolidinethione
  • Cyclic dithiocarbamic acid ester
  • Thiazolidine
  • Dithiocarbamic acid ester
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.25 g/LALOGPS
logP-0.23ALOGPS
logP0.72ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.34 m³·mol⁻¹ChemAxon
Polarizability14.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.99831661259
DarkChem[M-H]-126.26431661259
DeepCCS[M+H]+133.29830932474
DeepCCS[M-H]-131.03730932474
DeepCCS[M-2H]-167.29830932474
DeepCCS[M+Na]+142.30630932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.332859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-131.932859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Raphanusamic acidOC(=O)C1CSC(=S)N13145.0Standard polar33892256
Raphanusamic acidOC(=O)C1CSC(=S)N11496.2Standard non polar33892256
Raphanusamic acidOC(=O)C1CSC(=S)N11980.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Raphanusamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1CSC(=S)N11762.7Semi standard non polar33892256
Raphanusamic acid,1TMS,isomer #2C[Si](C)(C)N1C(=S)SCC1C(=O)O1784.9Semi standard non polar33892256
Raphanusamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CSC(=S)N1[Si](C)(C)C1783.2Semi standard non polar33892256
Raphanusamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CSC(=S)N1[Si](C)(C)C1786.2Standard non polar33892256
Raphanusamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSC(=S)N11972.8Semi standard non polar33892256
Raphanusamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=S)SCC1C(=O)O2020.2Semi standard non polar33892256
Raphanusamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSC(=S)N1[Si](C)(C)C(C)(C)C2216.2Semi standard non polar33892256
Raphanusamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSC(=S)N1[Si](C)(C)C(C)(C)C2322.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Raphanusamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-6900000000-8fca1e7c9fe934fb781c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Raphanusamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-014i-8910000000-da94e7c4071ab3f72bde2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Raphanusamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Raphanusamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 10V, Positive-QTOFsplash10-03dj-1900000000-299dc6ceac35c33928342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 20V, Positive-QTOFsplash10-02vj-1900000000-ac1b58d4228b8ba40ca32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 40V, Positive-QTOFsplash10-05fu-9000000000-b16d155561352d59e4952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 10V, Negative-QTOFsplash10-03di-0900000000-0f862f0871e44247ef052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 20V, Negative-QTOFsplash10-0a6r-9800000000-9bf9ade05e26c2d7bfd12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 40V, Negative-QTOFsplash10-0a4i-9100000000-97dae24deaaae1e8ffbe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 10V, Negative-QTOFsplash10-0a4i-9600000000-5c227d97f8b4f80bca532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 20V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-5321eec86325f32e6b782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 10V, Positive-QTOFsplash10-03xr-0900000000-1415617271138eb9dc752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 20V, Positive-QTOFsplash10-014i-1900000000-681eee89fa3a2456d1742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raphanusamic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-e893506aede7f851f4ec2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021196
KNApSAcK IDC00057720
Chemspider ID2299167
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3034757
PDB IDNot Available
ChEBI ID166452
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .