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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0000996
Secondary Accession Numbers
  • HMDB0060179
  • HMDB00996
  • HMDB60179
Metabolite Identification
Common Name3-Sulfinoalanine
Description3-Sulfinoalanine or cysteinesulfinic acid is an N-methyl-D-aspartate agonist. It is a product of cysteine dioxygenase or CDO (EC 1.13.11.20). In humans, cysteine catabolism is tightly regulated via regulation of cysteine dioxygenase (CDO) levels in the liver, with the turnover of CDO protein being dramatically decreased when intracellular cysteine levels increase. This occurs in response to changes in the intracellular cysteine concentration via changes in the rate of CDO ubiquitination and degradation. Expressed at high levels in the liver with lower levels in the kidney, brain, and lung, cysteine dioxygenase catalyzes the addition of molecular oxygen to the sulfhydryl group of cysteine, yielding cysteinesulfinic acid. The oxidative catabolism of cysteine to cysteinesulfinate by CDO represents an irreversible loss of cysteine from the free amino acid pool. Once generated, cysteinesulfinate is shuttled into several pathways including hypotaurine/taurine synthesis, sulfite/sulfate production, and the generation of pyruvate.
Structure
Data?1582752169
Synonyms
ValueSource
(2R)-2-Amino-3-sulfinopropanoic acidChEBI
3-Sulphino-L-alanineChEBI
L-Cysteinesulfinic acidChEBI
(2R)-2-Amino-3-sulfinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoic acidGenerator
3-Sulfino-L-alanineGenerator
L-CysteinesulfinateGenerator
L-CysteinesulphinateGenerator
L-Cysteinesulphinic acidGenerator
3-SulphinoalanineGenerator
3-Sulfinato-L-alaninic acidHMDB
3-Sulphinato-L-alaninateHMDB
3-Sulphinato-L-alaninic acidHMDB
Cysteine hydrogen sulfite esterHMDB
Alanine 3-sulfinic acidHMDB
Cysteine sulfinateHMDB
Cysteine sulfinic acidHMDB
3-Sulfinato-L-alaninateHMDB
Alanine-3-sulfinic acidHMDB
Alaninesulfinic acidHMDB
CysteinesulfinateHMDB
Cysteinesulfinic acidHMDB
L-2-Amino-3-sulfinopropionic acidHMDB
3-SulfinoalanineChEBI
Chemical FormulaC3H7NO4S
Average Molecular Weight153.157
Monoisotopic Molecular Weight153.009578407
IUPAC Name(2R)-2-amino-3-[(R)-sulfino]propanoic acid
Traditional Name3-sulfinoalanine
CAS Registry Number1115-65-7
SMILES
N[C@@H](CS(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
InChI KeyADVPTQAUNPRNPO-REOHCLBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Sulfinic acid
  • Sulfinic acid derivative
  • Alkanesulfinic acid or derivatives
  • Alkanesulfinic acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
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 Solubility54.6 g/LALOGPS
logP10(-2.1) g/LALOGPS
logP10(-3.8) g/LChemAxon
logS10(-0.7) g/LALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.99 m³·mol⁻¹ChemAxon
Polarizability12.95 ųChemAxon
Number of Rings0ChemAxon
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]+133.89831661259
DarkChem[M-H]-125.24231661259
AllCCS[M+H]+133.98432859911
AllCCS[M-H]-125.96732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-SulfinoalanineN[C@@H](CS(O)=O)C(O)=O2532.8Standard polar33892256
3-SulfinoalanineN[C@@H](CS(O)=O)C(O)=O1268.3Standard non polar33892256
3-SulfinoalanineN[C@@H](CS(O)=O)C(O)=O1780.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Sulfinoalanine,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O1485.3Semi standard non polar33892256
3-Sulfinoalanine,1TMS,isomer #2C[Si](C)(C)OS(=O)C[C@H](N)C(=O)O1513.4Semi standard non polar33892256
3-Sulfinoalanine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O1568.1Semi standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C1534.7Semi standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C1856.2Standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C2286.9Standard polar33892256
3-Sulfinoalanine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C1604.6Semi standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C1884.9Standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C2140.8Standard polar33892256
3-Sulfinoalanine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O1617.4Semi standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O1823.0Standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O2240.4Standard polar33892256
3-Sulfinoalanine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C1732.6Semi standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C1902.9Standard non polar33892256
3-Sulfinoalanine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C2359.0Standard polar33892256
3-Sulfinoalanine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1651.0Semi standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1953.3Standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1860.6Standard polar33892256
3-Sulfinoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C1745.1Semi standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C2031.1Standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C1994.6Standard polar33892256
3-Sulfinoalanine,3TMS,isomer #3C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1753.5Semi standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #3C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1963.8Standard non polar33892256
3-Sulfinoalanine,3TMS,isomer #3C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2009.6Standard polar33892256
3-Sulfinoalanine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1812.8Semi standard non polar33892256
3-Sulfinoalanine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2066.5Standard non polar33892256
3-Sulfinoalanine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1788.4Standard polar33892256
3-Sulfinoalanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O1744.8Semi standard non polar33892256
3-Sulfinoalanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)C[C@H](N)C(=O)O1773.8Semi standard non polar33892256
3-Sulfinoalanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O1825.1Semi standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C2002.4Semi standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C2435.3Standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C2350.0Standard polar33892256
3-Sulfinoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2052.6Semi standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2485.8Standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2263.0Standard polar33892256
3-Sulfinoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2060.3Semi standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2380.1Standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2302.7Standard polar33892256
3-Sulfinoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2195.3Semi standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2405.4Standard non polar33892256
3-Sulfinoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2351.3Standard polar33892256
3-Sulfinoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2292.8Semi standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2709.3Standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2223.7Standard polar33892256
3-Sulfinoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2436.2Semi standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2803.2Standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2291.0Standard polar33892256
3-Sulfinoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2416.5Semi standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2691.9Standard non polar33892256
3-Sulfinoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2287.4Standard polar33892256
3-Sulfinoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2669.4Semi standard non polar33892256
3-Sulfinoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3026.6Standard non polar33892256
3-Sulfinoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2264.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Sulfinoalanine GC-MS (3 TMS)splash10-0gbi-1940000000-6f5b1dbc8f18bf19a1ba2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Sulfinoalanine EI-B (Non-derivatized)splash10-0uxr-0960000000-763d242d0ca2b186b6582017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Sulfinoalanine GC-EI-TOF (Non-derivatized)splash10-0uy0-0930000000-702fcc20f2a851fa2e6d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-1c518aa1229684a41ad62017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7900000000-c7e561e94593d4ba17df2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOFsplash10-0udi-2900000000-9b7727f6206fcc55e6712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-1d1369a5e4254a8a3d132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-2d3ebcfaec61e7e367772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOFsplash10-03dr-9000000000-7b240ef61fb159b7bfaf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOFsplash10-03di-9000000000-c2f11bb79389426519552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , negative-QTOFsplash10-000i-9000000000-000940516fee7eeb55212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , negative-QTOFsplash10-000i-9000000000-178c25e031c7d69082562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine , negative-QTOFsplash10-000i-9000000000-245b34836035470b4abe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOFsplash10-0udr-4900000000-260a6f39fe371359dc232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOFsplash10-00di-9400000000-25d12760dd813f0fa0872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOFsplash10-00di-9300000000-97e345cd50da1d6cff012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOFsplash10-0096-9100000000-b40b8be15e2a1f73f8282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOFsplash10-0a6r-9000000000-74510742c38b337763492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-5bea4c5d79e7334083a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-242d94ad2d408f9da90c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine , positive-QTOFsplash10-0fki-8900000000-c2c0cb790e021c7e4e882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Negative-QTOFsplash10-03yj-9000000000-3f1105df9c6676560fb52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine 35V, Negative-QTOFsplash10-000i-9000000000-c73a90ab623312b8b4a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Negative-QTOFsplash10-000i-9000000000-76af07a82e5c1a229cb22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 10V, Positive-QTOFsplash10-0pbi-1900000000-37118160b153b5d34bf82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Positive-QTOFsplash10-0a5l-9800000000-81881a595728a3c4f9e82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Positive-QTOFsplash10-0006-9000000000-b6696507c06f0123a9422017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 10V, Negative-QTOFsplash10-0udi-3900000000-ac1441828c0aa5b222042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Negative-QTOFsplash10-0ik9-9500000000-c214c5e872f8b7db390c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Negative-QTOFsplash10-03di-9000000000-c766714b455939044f052017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.38 +/- 0.28 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0732 +/- 0.284 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.163 +/- 0.345 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.316 +/- 0.424 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.546 +/- 0.508 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.546 +/- 0.508 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.627 +/- 0.484 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified28.4 +/- 7.7 uMChildren (1-13 years old)Not SpecifiedMethotrexate treatment details
Associated Disorders and Diseases
Disease References
Methotrexate treatment
  1. Quinn CT, Griener JC, Bottiglieri T, Hyland K, Farrow A, Kamen BA: Elevation of homocysteine and excitatory amino acid neurotransmitters in the CSF of children who receive methotrexate for the treatment of cancer. J Clin Oncol. 1997 Aug;15(8):2800-6. [PubMed:9256122 ]
Associated OMIM IDsNone
DrugBank IDDB02153
Phenol Explorer Compound IDNot Available
FooDB IDFDB022358
KNApSAcK IDNot Available
Chemspider ID1266065
KEGG Compound IDC00606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCysteine_sulfinic_acid
METLIN IDNot Available
PubChem Compound1549098
PDB IDCSD
ChEBI ID16345
Food Biomarker OntologyNot Available
VMH ID3SALA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKissman, Henry M.; Baker, B. R. Preparation of various amides of p-methoxy-L-phenylalanine. Journal of Medicinal & Pharmaceutical Chemistry (1960), 2 415-23.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lin SY, Nui DM, Tu CP, Cheng YD, Lin HL: Evidence of L-cysteinesulfinic acid in PKU neonatal hair roots, with disappearance after dietary control. Ultrastruct Pathol. 2000 Sep-Oct;24(5):351-2. [PubMed:11071575 ]
  2. Hoeltzli SD, Kelley LK, Moe AJ, Smith CH: Anionic amino acid transport systems in isolated basal plasma membrane of human placenta. Am J Physiol. 1990 Jul;259(1 Pt 1):C47-55. [PubMed:1973601 ]
  3. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD2
Uniprot ID:
Q05329
Molecular weight:
65410.77
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q99259
Molecular weight:
66896.065
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
Reactions
3-Sulfinoalanine → Hypotaurine + CO(2)details
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in iron ion binding
Specific function:
Initiates several important metabolic pathways related to pyruvate and several sulfurate compounds including sulfate, hypotaurine and taurine. Critical regulator of cellular cysteine concentrations. Has an important role in maintaining the hepatic concentation of intracellular free cysteine within a proper narrow range.
Gene Name:
CDO1
Uniprot ID:
Q16878
Molecular weight:
22971.745
Reactions
L-Cysteine + Oxygen → 3-Sulfinoalaninedetails
General function:
Involved in iron ion binding
Specific function:
L-CYSTEINE + O(2) = 3-SULFINOALANINE
Gene Name:
CDO-1
Uniprot ID:
Q16857
Molecular weight:
6589.4