Showing metabocard for 3-Sulfinoalanine (BMDB0000996)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:39 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0000996
Secondary Accession Numbers
  • BMDB00996
Metabolite Identification
Common Name3-Sulfinoalanine
Description3-Sulfinoalanine, also known as cysteine-S-dioxide or cysteine sulfinate, 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. 3-Sulfinoalanine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-Sulfinoalanine exists in all living species, ranging from bacteria to humans. 3-Sulfinoalanine participates in a number of enzymatic reactions, within cattle. In particular, 3-Sulfinoalanine can be biosynthesized from L-cysteine; which is mediated by the enzyme cysteine dioxygenase type 1. Furthermore, 3-Sulfinoalanine can be converted into hypotaurine through the action of the enzyme cysteine sulfinic acid decarboxylase. Furthermore, 3-Sulfinoalanine and oxoglutaric acid can be converted into 3-sulfinylpyruvic acid and L-glutamic acid through its interaction with the enzyme aspartate aminotransferase, cytoplasmic. Finally, 3-Sulfinoalanine can be biosynthesized from L-cysteine through its interaction with the enzyme cysteine dioxygenase type 1. In cattle, 3-sulfinoalanine is involved in a couple of metabolic pathways, which include the taurine and hypotaurine metabolism pathway and the cysteine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3.8ChemAxon
logS-0.7ALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000996
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
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)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

Enzyme Details
1. Aspartate aminotransferase, cytoplasmic
General function:
Amino acid transport and metabolism
Specific function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain (By similarity).
Gene Name:
GOT1
Uniprot ID:
P33097
Molecular weight:
46399.0
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + L-Glutamic aciddetails
Enzyme Details
2. Cysteine dioxygenase type 1
General function:
Involved in cysteine dioxygenase activity
Specific function:
Not Available
Gene Name:
CDO1
Uniprot ID:
Q3SZU4
Molecular weight:
23013.0
Reactions
L-Cysteine + Oxygen → 3-Sulfinoalaninedetails
Enzyme Details
3. 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
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
Enzyme Details
4. 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
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails