MiMeDB: Showing metabocard for 3-Sulfinoalanine (MMDBc0000381)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:31 UTC

Update Date

2024-10-15 19:42:23 UTC

Metabolite ID

MMDBc0000381

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 SDF PDB SMILES InChI

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

Molecular Formula

C₃H₇NO₄S

Average Mass

153.157

Monoisotopic Mass

153.009578407

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Saliva

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191953	Aspartate aminotransferase, cytoplasmic	Enzyme	P17174	Homo sapiens
MMDBp0191954	Aspartate aminotransferase, mitochondrial	Enzyme	P00505	Homo sapiens
MMDBp0192341	Glutamate decarboxylase 2	Enzyme	Q05329	Homo sapiens
MMDBp0192342	Glutamate decarboxylase 1	Enzyme	Q99259	Homo sapiens
MMDBp0192554	Cysteine sulfinic acid decarboxylase	Enzyme	Q9Y600	Homo sapiens
MMDBp0192566	Cysteine dioxygenase type 1	Unknown	Q16878	Homo sapiens
MMDBp0196284	Cysteine dioxygenase	Enzyme	Q16857	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000081	3-Sulfinoalanine	Hypotaurine	cysteine sulfinic acid decarboxylase	VMH	30371894
MMDBr0000082	3-Sulfinoalanine	Cysteic acid	Not Available	VMH	30371894
MMDBr0000083	3-Sulfinoalanine	3-Sulfinylpyruvic acid	glutamic-oxaloacetic transaminase 1, soluble	VMH	3346220
MMDBr0000084	3-Sulfinoalanine	3-Sulfinylpyruvic acid	glutamic-oxaloacetic transaminase 2, mitochondrial	VMH	3346220
MMDBr0000565	L-Cysteine	3-Sulfinoalanine	cysteine dioxygenase type 1	VMH; KEGG	14514920

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human stool; Human ; Human urine; Human feces; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	nah	1
Archaea/Archaea	Euryarchaeota	1
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	28.4	7.7	uM	Children (1-13 years old)	Not Specified	Methotrexate treatment	HMDB	9256122
Human Blood	Detected and Quantified	1.38	0.28	uM	Adult (>18 years old)	Both	Normal	HMDB	7978266
Human Saliva	Detected and Quantified	0.0732	0.284	uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.163	0.345	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.316	0.424	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.546	0.508	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.546	0.508	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.627	0.484	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Cerebrospinal fluid (csf)	Detected but not Quantified				Children (1-13 years old)	Not Specified	Normal	HMDB	9256122
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000996

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

References

Synthesis Reference

Not Available

General 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. doi: 10.1152/ajpcell.1990.259.1.C47. [PubMed:1973601 ]
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. doi: 10.1080/019131200750035094. [PubMed:11071575 ]
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 ]

Showing metabocard for 3-Sulfinoalanine (MMDBc0000381)

MOL for #<Metabolite:0x00007fdafabd0790>

3D MOL for #<Metabolite:0x00007fdafabd0790>

3D SDF for #<Metabolite:0x00007fdafabd0790>

3D-SDF for #<Metabolite:0x00007fdafabd0790>

PDB for #<Metabolite:0x00007fdafabd0790>

3D PDB for #<Metabolite:0x00007fdafabd0790>

SMILES for #<Metabolite:0x00007fdafabd0790>

INCHI for #<Metabolite:0x00007fdafabd0790>

Structure for #<Metabolite:0x00007fdafabd0790>

3D Structure for #<Metabolite:0x00007fdafabd0790>