ECMDB: 3-Sulfinoalanine (ECMDB00996) (M2MDB000218)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (562)

Record Information

Version

2.0

Creation Date

2012-05-31 13:03:03 -0600

Update Date

2015-09-13 12:56:09 -0600

Secondary Accession Numbers

ECMDB00996

Identification

Name:

3-Sulfinoalanine

Description

3-Sulfinoalanine or cysteinesulfinic acid is a N-methyl-D-aspartate agonist. It is a prodcut of cysteine dioxygenase or CDO [EC 1.13.11.20]. 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 SDF PDB SMILES InChI

Synonyms:

3-Sulfino- Alanine
3-Sulfino-L-alanine
3-Sulphino- Alanine
3-Sulphino-L-alanine
3-Sulphinoalanine
Alanine 3-sulfinate
Alanine 3-sulfinic acid
Alanine 3-sulphinate
Alanine 3-sulphinic acid
Cysteine hydrogen sulfite ester
Cysteine hydrogen sulphite ester
Cysteine sulfinate
Cysteine sulfinic acid
Cysteine sulphinate
Cysteine sulphinic acid
Cysteine-sulfinate
Cysteine-sulfinic acid
Cysteine-sulphinate
Cysteine-sulphinic acid
L-Cysteine sulfinate
L-Cysteine sulfinic acid
L-Cysteine sulphinate
L-Cysteine sulphinic acid
L-Cysteinesulfinate
L-Cysteinesulfinic acid
L-Cysteinesulphinate
L-Cysteinesulphinic acid

Chemical Formula:

C₃H₇NO₄S

Weight:

Average: 153.157
Monoisotopic: 153.009578407

InChI Key:

WVMUCBHSEHBMKA-REOHCLBHSA-N

InChI:

InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2,9H,1,4H2,(H,5,6)/t2-/m0/s1

CAS number:

1115-65-7

IUPAC Name:

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional IUPAC Name:

udp-α-D-glucose

SMILES:

N[C@@H](CS(=O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Lactam
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-D-glucose (CHEBI:46229 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	291.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	45.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

3-Sulfinoalanine + 2 Hydrogen ion > L-Alanine + Sulfur dioxide
3-Sulfinoalanine <> Hypotaurine + Carbon dioxide
3-Sulfinoalanine + alpha-Ketoglutarate <> 3-Sulfinylpyruvic acid + L-Glutamate
3-Sulfinoalanine + Water Hydrogen ion + L-Alanine + Sulfite
3-Sulfinoalanine > Hypotaurine + Carbon dioxide + Hypotaurine

SMPDB Pathways:

Not Available

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Taurine and hypotaurine metabolism ec00430

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054k-3933570000-89f658b2d26ff158d84c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-4942706000-3a83736296429f83adee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucose,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0000090000-1692ab5f5dad1cf7e436	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-015a-0439510000-69e7cd4c2c365a24706b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0109-5753970000-03f34041208ba93ef87a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00fr-9257000000-73b85a465d99ce92467d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00ba-9333000000-b57dc1340555f1a997b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00fr-9257000000-ba1e6c754b8f04d5b659	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-9bd63595c19dbe18d143	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-4b94aa10fd96d2d9c505	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-996cd4acdaa34c877460	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-4b81825405869909992e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-6fd09254750e77963110	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-03a2a98eb0aa84737530	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4901260000-8396a090c14de7f2d708	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-8907020000-94410556a0288cb8167b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5901000000-10132c85ad33464d4eef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0000960000-6404d8d944e1ae6f30e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07e1-2322960000-6af539ce21752f9023ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-9732000000-b0c81adc41b1d799e1e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-8cab8f2bc0fb9e9e8ba9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057j-9203870000-d60681ff91f741bdb867	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3519000000-67ca2f9355ef7f94a47d	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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)

Links

External Links:

Resource	Link
CHEBI ID	16345
HMDB ID	HMDB00996
Pubchem Compound ID	109
Kegg ID	C00606
ChemSpider ID	16743745
Wikipedia ID	Uridine_diphosphate_glucose
BioCyc ID	3-SULFINOALANINE
EcoCyc ID	3-SULFINOALANINE
Ligand Expo	CSW

Enzymes

Protein Details

1. Aspartate aminotransferase

General function:: Involved in transferase activity
Specific function:: L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name:: aspC
Uniprot ID:: P00509
Molecular weight:: 43573

Reactions

L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate.

Protein Details

2. Glutamate decarboxylase alpha

General function:: Involved in glutamate decarboxylase activity
Specific function:: Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:: gadA
Uniprot ID:: P69908
Molecular weight:: 52685

Reactions

L-glutamate = 4-aminobutanoate + CO(2).

Protein Details

3. Glutamate decarboxylase beta

General function:: Involved in glutamate decarboxylase activity
Specific function:: Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:: gadB
Uniprot ID:: P69910
Molecular weight:: 52668

Reactions

L-glutamate = 4-aminobutanoate + CO(2).

Protein Details

4. Cysteine sulfinate desulfinase

General function:: Involved in metabolic process
Specific function:: Catalyzes the removal of elemental sulfur and selenium atoms from L-cysteine, L-cystine, L-selenocysteine, and L- selenocystine to produce L-alanine. L-cysteine sulfinic acid is the best substrate. Functions as a selenium delivery protein in the pathway for the biosynthesis of selenophosphate
Gene Name:: csdA
Uniprot ID:: Q46925
Molecular weight:: 43234

3-Sulfinoalanine (ECMDB00996) (M2MDB000218)

Structure for #<Compound:0xae44b070>

Enzymes

Reactions

Reactions

Reactions