Milk Composition Database: Showing metabocard for 3-Sulfinoalanine (BMDB0000996)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:39:39 UTC

Update Date

2020-05-21 16:28:30 UTC

MCDB ID

BMDB0000996

Secondary Accession Numbers

BMDB00996

Metabolite Identification

Common Name

3-Sulfinoalanine

Description

3-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

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

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 )

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	-2.1	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gbi-1940000000-6f5b1dbc8f18bf19a1ba	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uxr-0960000000-763d242d0ca2b186b658	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uy0-0930000000-702fcc20f2a851fa2e6d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-1c518aa1229684a41ad6	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-7900000000-c7e561e94593d4ba17df	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-9b7727f6206fcc55e671	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-1d1369a5e4254a8a3d13	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-2d3ebcfaec61e7e36777	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03dr-9000000000-7b240ef61fb159b7bfaf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-9000000000-c2f11bb7938942651955	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-9000000000-000940516fee7eeb5521	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-9000000000-178c25e031c7d6908256	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9000000000-245b34836035470b4abe	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-4900000000-260a6f39fe371359dc23	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9400000000-25d12760dd813f0fa087	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9300000000-97e345cd50da1d6cff01	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0096-9100000000-b40b8be15e2a1f73f828	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a6r-9000000000-74510742c38b33776349	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-5bea4c5d79e7334083a8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-242d94ad2d408f9da90c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0fki-8900000000-c2c0cb790e021c7e4e88	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03yj-9000000000-3f1105df9c6676560fb5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-c73a90ab623312b8b4a9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-76af07a82e5c1a229cb2	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1900000000-37118160b153b5d34bf8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5l-9800000000-81881a595728a3c4f9e8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b6696507c06f0123a942	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-ac1441828c0aa5b22204	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ik9-9500000000-c214c5e872f8b7db390c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-c766714b455939044f05	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29565828	details

External Links

HMDB ID

HMDB0000996

DrugBank ID

DB02153

Phenol Explorer Compound ID

Not Available

FoodDB 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

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

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 ]

Showing metabocard for 3-Sulfinoalanine (BMDB0000996)

Structure for BMDB0000996 (3-Sulfinoalanine)