Bovine Metabolome Database: Showing metabocard for Cysteic acid (BMDB0002757)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:01:33 UTC

Update Date

2020-05-21 16:26:59 UTC

BMDB ID

BMDB0002757

Secondary Accession Numbers

BMDB02757

Metabolite Identification

Common Name

Cysteic acid

Description

Cysteic acid, also known as cysteic acid or Cysteic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Cysteic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Cysteic acid exists in all living species, ranging from bacteria to humans. Cysteic acid participates in a number of enzymatic reactions, within cattle. In particular, Cysteic acid can be converted into taurine through the action of the enzyme cysteine sulfinic acid decarboxylase. In addition, Cysteic acid can be converted into taurine; which is catalyzed by the enzyme glutamate decarboxylase 1. In cattle, cysteic acid is involved in the metabolic pathway called the taurine and hypotaurine metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Sulfoalanine	ChEBI
beta-Sulfoalanine	ChEBI
Cysteine sulfonic acid	ChEBI
3-Sulphoalanine	Generator
b-Sulfoalanine	Generator
b-Sulphoalanine	Generator
beta-Sulphoalanine	Generator
Β-sulfoalanine	Generator
Β-sulphoalanine	Generator
Cysteine sulfonate	Generator
Cysteine sulphonate	Generator
Cysteine sulphonic acid	Generator
Cysteate	Generator
2-Amino-3-sulfopropanoate	HMDB
2-Amino-3-sulfopropanoic acid	HMDB
2-Amino-3-sulfopropionate	HMDB
2-Amino-3-sulfopropionic acid	HMDB
Cepteate	HMDB
Cepteic acid	HMDB
Cipteate	HMDB
Cipteic acid	HMDB
Cysteinate	HMDB
Cysteinesulfonate	HMDB
Cysteinesulfonic acid	HMDB
Cysteinic acid	HMDB
Cysterate	HMDB
Cysteric acid	HMDB
L-Cysteate	HMDB
L-Cysteic acid	HMDB
3 Sulfoalanine	HMDB
Acid, cysteic	HMDB
beta Sulfoalanine	HMDB

Chemical Formula

C₃H₇NO₅S

Average Molecular Weight

169.156

Monoisotopic Molecular Weight

169.004493029

IUPAC Name

2-amino-3-sulfopropanoic acid

Traditional Name

cysteic acid

CAS Registry Number

498-40-8

SMILES

NC(CS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)

InChI Key

XVOYSCVBGLVSOL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:21260 )
amino sulfonic acid (CHEBI:21260 )
alanine derivative (CHEBI:21260 )
carboxyalkanesulfonic acid (CHEBI:21260 )
cysteine derivative (CHEBI:21260 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Mitochondria

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-3	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.44 m³·mol⁻¹	ChemAxon
Polarizability	13.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-4987d9a40ecc2c214dc3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9200000000-63aac0a32cfc85b50ddd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-e495810d64e3e38da2bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uxr-0900000000-02df293f7975b82ac3b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-47bca80f8407522228fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-45eccf44b0be54ef5703	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-9800000000-32b77b0eb11d32fe32bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-47bca80f8407522228fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6103b341ba1eeaf705ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-b3cbcae68d66f83d26cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0159-9800000000-c9f345d26f9e3b45c607	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-e31af2162892af224283	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-d763c2e7d917148c530c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-0158ea55e5c9dfde9dc7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0089-9000000000-510d6054b2f3b09e2920	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cfa2835cc0b2b29ec110	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-aa53bbb90f5cdd3a6d83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-3900000000-0626b1961d0517861451	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-29ef424c41f3119ec633	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cc1dd155bb25f8c9a20f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-2900000000-8fc583c963f43919bf50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-1900000000-00b8a4b9bbedfa9bf252	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9800000000-18c40d4b99159222b563	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-7a313e5ca76d5a55eb56	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-5900000000-967c249c15d798909745	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9200000000-c02c1daafa3bc2cec519	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-80973e7856292311a36d	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Taurine and Hypotaurine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002757

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023061

KNApSAcK ID

Not Available

Chemspider ID

23942

KEGG Compound ID

C00506

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

21260

References

Synthesis Reference

Zhao, Chong-tao; Wang, Qing-ping; Lin, Wan-zhen; Chen, Ping. Synthesis of L-cysteic acid by indirect electrooxidation. Jingxi Huagong (2003), 20(4), 237-238, 253.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Glutamate decarboxylase 1

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the production of GABA.
Gene Name:: GAD1
Uniprot ID:: Q0VCA1
Molecular weight:: 66784.0

Reactions

Cysteic acid → Taurine + Carbon dioxide	details

Enzyme Details

2. Acidic amino acid decarboxylase GADL1

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the decarboxylation of L-aspartate, 3-sulfino-L-alanine (cysteine sulfinic acid), and L-cysteate to beta-alanine, hypotaurine and taurine, respectively. The preferred substrate is L-aspartate. Does not exhibit any decarboxylation activity toward glutamate.
Gene Name:: GADL1
Uniprot ID:: A6QM00
Molecular weight:: 59380.0

Reactions

Cysteic acid → Taurine + Carbon dioxide	details

Showing metabocard for Cysteic acid (BMDB0002757)

Structure for BMDB0002757 (Cysteic acid)

Enzymes

Reactions

Reactions