Showing Compound Thiocysteine (FDB023203)

Record Information

Version

1.0

Creation date

2011-09-21 00:26:16 UTC

Update date

2015-07-21 06:57:35 UTC

Primary ID

FDB023203

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Thiocysteine

Description

The reactive species in the phosphofructokinase modulation system could be considered thiocysteine (R-S-S-) or cystine trisulfide (R-S-S-S-R) produced from cystine in the presence of gamma-Cystathionase (CST, EC 4.4.1.1). The desulfuration reaction of cystine in vivo produces thiocysteine containing a bound sulfur atom. Persulfide generated from L-cysteine inactivates tyrosine aminotransferase. Thiocysteine is the reactive (unstable) intermediate of thiocystine which functions as a persulfide in transferring its sulfane sulfur to thiophilic acceptors. Thiocystine conversion to unstable thiocysteine is accelerated by sulfhydryl compounds, or reagents that cleave sulfur-sulfur bonds to yield sulfhydryl groups. Thiocystine is proposed as the storage form of sulfane sulfur in biological systems. Liver cytosols contain factors that produce an inhibitor of tyrosine aminotransferase in 3 steps: initial oxidation of cysteine to form cystine; desulfurization of cystine catalyzed by cystathionase to form the persulfide, thiocysteine; and reaction of thiocysteine (or products of its decomposition) with proteins to form protein-bound sulfane. (PMID: 2903161, 454618, 7287665) [HMDB]

CAS Number

5652-32-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S)-2-Amino-3-disulfanylpropanoate	HMDB
(2S)-2-Amino-3-disulphanylpropanoate	HMDB
(2S)-2-Amino-3-disulphanylpropanoic acid	HMDB
3-(Thiosulfeno)-alanine	HMDB
3-(thiosulfeno)-Alanine	hmdb
3-Disulfanyl-L-alanine	HMDB

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	14.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.04	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.99 m³·mol⁻¹	ChemAxon
Polarizability	14.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H7NO2S2

IUPAC name

(2S)-2-amino-3-disulfanylpropanoic acid

InChI Identifier

InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1

InChI Key

XBKONSCREBSMCS-UWTATZPHSA-N

Isomeric SMILES

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

Average Molecular Weight

153.223

Monoisotopic Molecular Weight

152.991819853

Classification

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
D-alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
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

Not Available

Ontology

Disposition

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Thiocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002f-9200000000-2698595247d44144b386	Spectrum
Predicted GC-MS	Thiocysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9300000000-df6a4d15744f12f2dc0f	Spectrum
Predicted GC-MS	Thiocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-5900000000-cebf11d68c2df85b1cc8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-5900000000-9adeada6729d7a30cbb0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c9351f3fcc5c9de3b7e3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-9700000000-8561e1934a1ae7f329e1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fni-9200000000-df6a2ea2c3d324acdedb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-a4fc4e46a9085d75f7e5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-9500000000-ad5cda072821948874e7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-5754d7edf423fce93e4d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-bda92f13cfa445b06160	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-7414a6c098c4cecae0f6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9500000000-da0c13ae52cf2b812c28	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-df2fb47319062974eb55	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C01962

Pubchem Compound ID

439614

Pubchem Substance ID

Not Available

ChEBI ID

28839

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03585

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

38786

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB