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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:22 UTC

HMDB ID

HMDB0000996

Secondary Accession Numbers

HMDB0060179
HMDB00996
HMDB60179

Metabolite Identification

Common Name

3-Sulfinoalanine

Description

3-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R)-2-Amino-3-sulfinopropanoic acid	ChEBI
3-Sulphino-L-alanine	ChEBI
L-Cysteinesulfinic acid	ChEBI
(2R)-2-Amino-3-sulfinopropanoate	Generator
(2R)-2-Amino-3-sulphinopropanoate	Generator
(2R)-2-Amino-3-sulphinopropanoic acid	Generator
3-Sulfino-L-alanine	Generator
L-Cysteinesulfinate	Generator
L-Cysteinesulphinate	Generator
L-Cysteinesulphinic acid	Generator
3-Sulphinoalanine	Generator
3-Sulfinato-L-alaninic acid	HMDB
3-Sulphinato-L-alaninate	HMDB
3-Sulphinato-L-alaninic acid	HMDB
Cysteine hydrogen sulfite ester	HMDB
Alanine 3-sulfinic acid	HMDB
Cysteine sulfinate	HMDB
Cysteine sulfinic acid	HMDB
3-Sulfinato-L-alaninate	HMDB
Alanine-3-sulfinic acid	HMDB
Alaninesulfinic acid	HMDB
Cysteinesulfinate	HMDB
Cysteinesulfinic acid	HMDB
L-2-Amino-3-sulfinopropionic acid	HMDB
3-Sulfinoalanine	ChEBI

Chemical Formula

C₃H₇NO₄S

Average Molecular Weight

153.157

Monoisotopic Molecular Weight

153.009578407

IUPAC Name

(2R)-2-amino-3-[(R)-sulfino]propanoic acid

Traditional Name

3-sulfinoalanine

CAS Registry Number

1115-65-7

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 Key

ADVPTQAUNPRNPO-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted L-cysteine (CHEBI:16345 )
organosulfinic acid (CHEBI:16345 )
Other amino acids (C00606 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	54.6 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.8	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	1.12	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.99 m³·mol⁻¹	ChemAxon
Polarizability	12.95 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.898	31661259
DarkChem	[M-H]-	125.242	31661259
AllCCS	[M+H]+	133.984	32859911
AllCCS	[M-H]-	125.967	32859911
DeepCCS	[M+H]+	122.747	30932474
DeepCCS	[M-H]-	118.88	30932474
DeepCCS	[M-2H]-	156.447	30932474
DeepCCS	[M+Na]+	131.707	30932474
AllCCS	[M+H]+	134.0	32859911
AllCCS	[M+H-H2O]+	130.0	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	126.0	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	131.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	0.61 minutes	32390414
Predicted by Siyang on May 30, 2022	10.184 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	427.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	553.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	376.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	33.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	116.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	226.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	927.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	625.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	745.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	732.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	467.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	489.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Sulfinoalanine	N[C@@H](CS(O)=O)C(O)=O	2532.8	Standard polar	33892256
3-Sulfinoalanine	N[C@@H](CS(O)=O)C(O)=O	1268.3	Standard non polar	33892256
3-Sulfinoalanine	N[C@@H](CS(O)=O)C(O)=O	1780.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Sulfinoalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O	1485.3	Semi standard non polar	33892256
3-Sulfinoalanine,1TMS,isomer #2	C[Si](C)(C)OS(=O)C[C@H](N)C(=O)O	1513.4	Semi standard non polar	33892256
3-Sulfinoalanine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O	1568.1	Semi standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C	1534.7	Semi standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C	1856.2	Standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C	2286.9	Standard polar	33892256
3-Sulfinoalanine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C	1604.6	Semi standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C	1884.9	Standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C	2140.8	Standard polar	33892256
3-Sulfinoalanine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O	1617.4	Semi standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O	1823.0	Standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O	2240.4	Standard polar	33892256
3-Sulfinoalanine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C	1732.6	Semi standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C	1902.9	Standard non polar	33892256
3-Sulfinoalanine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C	2359.0	Standard polar	33892256
3-Sulfinoalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1651.0	Semi standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1953.3	Standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1860.6	Standard polar	33892256
3-Sulfinoalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1745.1	Semi standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2031.1	Standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CS(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1994.6	Standard polar	33892256
3-Sulfinoalanine,3TMS,isomer #3	C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1753.5	Semi standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #3	C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1963.8	Standard non polar	33892256
3-Sulfinoalanine,3TMS,isomer #3	C[Si](C)(C)OS(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2009.6	Standard polar	33892256
3-Sulfinoalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1812.8	Semi standard non polar	33892256
3-Sulfinoalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2066.5	Standard non polar	33892256
3-Sulfinoalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CS(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1788.4	Standard polar	33892256
3-Sulfinoalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O	1744.8	Semi standard non polar	33892256
3-Sulfinoalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)C[C@H](N)C(=O)O	1773.8	Semi standard non polar	33892256
3-Sulfinoalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O	1825.1	Semi standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C	2002.4	Semi standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C	2435.3	Standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CS(=O)O[Si](C)(C)C(C)(C)C	2350.0	Standard polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2052.6	Semi standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2485.8	Standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2263.0	Standard polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2060.3	Semi standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2380.1	Standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CS(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2302.7	Standard polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2195.3	Semi standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2405.4	Standard non polar	33892256
3-Sulfinoalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CS(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2351.3	Standard polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #1	CC(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)C	2292.8	Semi standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #1	CC(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)C	2709.3	Standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #1	CC(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)C	2223.7	Standard polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #2	CC(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)C	2436.2	Semi standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #2	CC(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)C	2803.2	Standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #2	CC(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)C	2291.0	Standard polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #3	CC(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)C	2416.5	Semi standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #3	CC(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)C	2691.9	Standard non polar	33892256
3-Sulfinoalanine,3TBDMS,isomer #3	CC(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)C	2287.4	Standard polar	33892256
3-Sulfinoalanine,4TBDMS,isomer #1	CC(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)C	2669.4	Semi standard non polar	33892256
3-Sulfinoalanine,4TBDMS,isomer #1	CC(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)C	3026.6	Standard non polar	33892256
3-Sulfinoalanine,4TBDMS,isomer #1	CC(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)C	2264.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Sulfinoalanine GC-MS (3 TMS)	splash10-0gbi-1940000000-6f5b1dbc8f18bf19a1ba	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Sulfinoalanine EI-B (Non-derivatized)	splash10-0uxr-0960000000-763d242d0ca2b186b658	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Sulfinoalanine GC-EI-TOF (Non-derivatized)	splash10-0uy0-0930000000-702fcc20f2a851fa2e6d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-1c518aa1229684a41ad6	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-7900000000-c7e561e94593d4ba17df	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Sulfinoalanine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOF	splash10-0udi-2900000000-9b7727f6206fcc55e671	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOF	splash10-000i-9000000000-1d1369a5e4254a8a3d13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOF	splash10-000i-9000000000-2d3ebcfaec61e7e36777	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOF	splash10-03dr-9000000000-7b240ef61fb159b7bfaf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , negative-QTOF	splash10-03di-9000000000-c2f11bb7938942651955	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , negative-QTOF	splash10-000i-9000000000-000940516fee7eeb5521	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , negative-QTOF	splash10-000i-9000000000-178c25e031c7d6908256	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine , negative-QTOF	splash10-000i-9000000000-245b34836035470b4abe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOF	splash10-0udr-4900000000-260a6f39fe371359dc23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOF	splash10-00di-9400000000-25d12760dd813f0fa087	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOF	splash10-00di-9300000000-97e345cd50da1d6cff01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOF	splash10-0096-9100000000-b40b8be15e2a1f73f828	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-QQ , positive-QTOF	splash10-0a6r-9000000000-74510742c38b33776349	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , positive-QTOF	splash10-000i-0900000000-5bea4c5d79e7334083a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine LC-ESI-ITFT , positive-QTOF	splash10-000i-0900000000-242d94ad2d408f9da90c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine , positive-QTOF	splash10-0fki-8900000000-c2c0cb790e021c7e4e88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Negative-QTOF	splash10-03yj-9000000000-3f1105df9c6676560fb5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine 35V, Negative-QTOF	splash10-000i-9000000000-c73a90ab623312b8b4a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Negative-QTOF	splash10-000i-9000000000-76af07a82e5c1a229cb2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 10V, Positive-QTOF	splash10-0pbi-1900000000-37118160b153b5d34bf8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Positive-QTOF	splash10-0a5l-9800000000-81881a595728a3c4f9e8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Positive-QTOF	splash10-0006-9000000000-b6696507c06f0123a942	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 10V, Negative-QTOF	splash10-0udi-3900000000-ac1441828c0aa5b22204	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 20V, Negative-QTOF	splash10-0ik9-9500000000-c214c5e872f8b7db390c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Sulfinoalanine 40V, Negative-QTOF	splash10-03di-9000000000-c766714b455939044f05	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Taurine and Hypotaurine Metabolism
Cysteine Metabolism
Beta-mercaptolactate-cysteine disulfiduria		Not Available
Cystinosis, ocular nonnephropathic		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.38 +/- 0.28 uM	Adult (>18 years old)	Both	Normal	7978266	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	9256122	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.0732 +/- 0.284 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.163 +/- 0.345 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.316 +/- 0.424 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.546 +/- 0.508 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.546 +/- 0.508 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.627 +/- 0.484 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	28.4 +/- 7.7 uM	Children (1-13 years old)	Not Specified	Methotrexate treatment	9256122	details

Associated Disorders and Diseases

Disease References

Methotrexate treatment
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 IDs

None

External Links

DrugBank ID

DB02153

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022358

KNApSAcK ID

Not Available

Chemspider ID

1266065

KEGG Compound ID

C00606

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cysteine_sulfinic_acid

METLIN ID

Not Available

PubChem Compound

1549098

PDB ID

CSD

ChEBI ID

16345

Food Biomarker Ontology

Not Available

VMH ID

3SALA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kissman, 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

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 ]
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 ]
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 ]
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

Enzyme Details

1. Aspartate aminotransferase, cytoplasmic

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 + Glutamic acid	details

Enzyme Details

2. Aspartate aminotransferase, mitochondrial

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 + Glutamic acid	details

Enzyme Details

3. Glutamate decarboxylase 2

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 dioxide	details

Enzyme Details

4. Glutamate decarboxylase 1

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 dioxide	details

Enzyme Details

5. Cysteine sulfinic acid decarboxylase

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 dioxide	details

Enzyme Details

6. Cysteine dioxygenase type 1

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-Sulfinoalanine	details

Enzyme Details

7. Cysteine dioxygenase

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

Showing metabocard for 3-Sulfinoalanine (HMDB0000996)

MOL for HMDB0000996 (3-Sulfinoalanine)

3D MOL for HMDB0000996 (3-Sulfinoalanine)

3D SDF for HMDB0000996 (3-Sulfinoalanine)

3D-SDF for HMDB0000996 (3-Sulfinoalanine)

PDB for HMDB0000996 (3-Sulfinoalanine)

3D PDB for HMDB0000996 (3-Sulfinoalanine)

SMILES for HMDB0000996 (3-Sulfinoalanine)

INCHI for HMDB0000996 (3-Sulfinoalanine)

Structure for HMDB0000996 (3-Sulfinoalanine)

3D Structure for HMDB0000996 (3-Sulfinoalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

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