Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 00:53:44 UTC

Update Date

2023-02-21 17:16:45 UTC

HMDB ID

HMDB0003585

Secondary Accession Numbers

HMDB0006337
HMDB03585
HMDB06337

Metabolite Identification

Common 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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(Thiosulfeno)-alanine	HMDB
3-Disulfanyl-L-alanine	HMDB
(2S)-2-Amino-3-disulfanylpropanoate	HMDB
(2S)-2-Amino-3-disulphanylpropanoate	HMDB
(2S)-2-Amino-3-disulphanylpropanoic acid	HMDB

Chemical Formula

C₃H₇NO₂S₂

Average Molecular Weight

153.223

Monoisotopic Molecular Weight

152.991819853

IUPAC Name

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

Traditional Name

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

CAS Registry Number

5652-32-4

SMILES

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

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

Chemical Taxonomy

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

Not Available

Exogenous (HMDB: HMDB0003585)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0003585)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.917	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.431	31661259
DarkChem	[M-H]-	126.528	31661259
DeepCCS	[M+H]+	126.385	30932474
DeepCCS	[M-H]-	123.408	30932474
DeepCCS	[M-2H]-	159.963	30932474
DeepCCS	[M+Na]+	134.949	30932474
AllCCS	[M+H]+	134.5	32859911
AllCCS	[M+H-H2O]+	130.6	32859911
AllCCS	[M+NH4]+	138.2	32859911
AllCCS	[M+Na]+	139.2	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	0.66 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4031 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	365.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	634.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	48.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	233.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	284.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	236.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	794.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	614.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	36.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	754.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	608.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	367.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiocysteine	N[C@H](CSS)C(O)=O	2534.9	Standard polar	33892256
Thiocysteine	N[C@H](CSS)C(O)=O	1382.6	Standard non polar	33892256
Thiocysteine	N[C@H](CSS)C(O)=O	1677.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiocysteine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](N)CSS	1528.0	Semi standard non polar	33892256
Thiocysteine,1TMS,isomer #2	C[Si](C)(C)SSC[C@@H](N)C(=O)O	1629.5	Semi standard non polar	33892256
Thiocysteine,1TMS,isomer #3	C[Si](C)(C)N[C@H](CSS)C(=O)O	1599.1	Semi standard non polar	33892256
Thiocysteine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C	1656.7	Semi standard non polar	33892256
Thiocysteine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C	1706.7	Standard non polar	33892256
Thiocysteine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C	2409.9	Standard polar	33892256
Thiocysteine,2TMS,isomer #2	C[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C	1651.9	Semi standard non polar	33892256
Thiocysteine,2TMS,isomer #2	C[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C	1596.4	Standard non polar	33892256
Thiocysteine,2TMS,isomer #2	C[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C	2141.0	Standard polar	33892256
Thiocysteine,2TMS,isomer #3	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O	1716.6	Semi standard non polar	33892256
Thiocysteine,2TMS,isomer #3	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O	1667.3	Standard non polar	33892256
Thiocysteine,2TMS,isomer #3	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O	2331.9	Standard polar	33892256
Thiocysteine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C	1760.7	Semi standard non polar	33892256
Thiocysteine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C	1623.7	Standard non polar	33892256
Thiocysteine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C	2376.4	Standard polar	33892256
Thiocysteine,3TMS,isomer #1	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O[Si](C)(C)C	1760.2	Semi standard non polar	33892256
Thiocysteine,3TMS,isomer #1	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O[Si](C)(C)C	1752.7	Standard non polar	33892256
Thiocysteine,3TMS,isomer #1	C[Si](C)(C)N[C@H](CSS[Si](C)(C)C)C(=O)O[Si](C)(C)C	1962.9	Standard polar	33892256
Thiocysteine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C)[Si](C)(C)C	1808.7	Semi standard non polar	33892256
Thiocysteine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C)[Si](C)(C)C	1762.7	Standard non polar	33892256
Thiocysteine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C)[Si](C)(C)C	2106.2	Standard polar	33892256
Thiocysteine,3TMS,isomer #3	C[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1871.5	Semi standard non polar	33892256
Thiocysteine,3TMS,isomer #3	C[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1824.0	Standard non polar	33892256
Thiocysteine,3TMS,isomer #3	C[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2108.7	Standard polar	33892256
Thiocysteine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1903.5	Semi standard non polar	33892256
Thiocysteine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1881.1	Standard non polar	33892256
Thiocysteine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1881.3	Standard polar	33892256
Thiocysteine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CSS	1777.1	Semi standard non polar	33892256
Thiocysteine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SSC[C@@H](N)C(=O)O	1878.5	Semi standard non polar	33892256
Thiocysteine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CSS)C(=O)O	1869.0	Semi standard non polar	33892256
Thiocysteine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C(C)(C)C	2181.8	Semi standard non polar	33892256
Thiocysteine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C(C)(C)C	2180.8	Standard non polar	33892256
Thiocysteine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CSS[Si](C)(C)C(C)(C)C	2448.6	Standard polar	33892256
Thiocysteine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C(C)(C)C	2134.1	Semi standard non polar	33892256
Thiocysteine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C(C)(C)C	2050.4	Standard non polar	33892256
Thiocysteine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](CSS)C(=O)O[Si](C)(C)C(C)(C)C	2353.1	Standard polar	33892256
Thiocysteine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O	2254.6	Semi standard non polar	33892256
Thiocysteine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O	2127.2	Standard non polar	33892256
Thiocysteine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O	2392.2	Standard polar	33892256
Thiocysteine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C(C)(C)C	2249.3	Semi standard non polar	33892256
Thiocysteine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C(C)(C)C	2078.7	Standard non polar	33892256
Thiocysteine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CSS)C(=O)O)[Si](C)(C)C(C)(C)C	2422.9	Standard polar	33892256
Thiocysteine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2485.7	Semi standard non polar	33892256
Thiocysteine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2395.6	Standard non polar	33892256
Thiocysteine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CSS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2301.4	Standard polar	33892256
Thiocysteine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2499.0	Semi standard non polar	33892256
Thiocysteine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2406.9	Standard non polar	33892256
Thiocysteine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2374.4	Standard polar	33892256
Thiocysteine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2601.0	Semi standard non polar	33892256
Thiocysteine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2452.8	Standard non polar	33892256
Thiocysteine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SSC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2362.8	Standard polar	33892256
Thiocysteine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2836.6	Semi standard non polar	33892256
Thiocysteine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2682.1	Standard non polar	33892256
Thiocysteine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CSS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2343.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiocysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9200000000-2698595247d44144b386	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiocysteine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-df6a4d15744f12f2dc0f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiocysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

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

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023203

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01962

BioCyc ID

Not Available

BiGG ID

38786

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439614

PDB ID

Not Available

ChEBI ID

28839

Food Biomarker Ontology

Not Available

VMH ID

THCYS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hargrove JL: Persulfide generated from L-cysteine inactivates tyrosine aminotransferase. Requirement for a protein with cysteine oxidase activity and gamma-cystathionase. J Biol Chem. 1988 Nov 25;263(33):17262-9. [PubMed:2903161 ]
Abdolrasulnia R, Wood JL: Transfer of persulfide sulfur from thiocystine to rhodanese. Biochim Biophys Acta. 1979 Mar 16;567(1):135-43. [PubMed:454618 ]
Yamanishi T, Tuboi S: The mechanism of the L-cystine cleavage reaction catalyzed by rat liver gamma-cystathionase. J Biochem. 1981 Jun;89(6):1913-21. [PubMed:7287665 ]

Enzymes

Enzyme Details

1. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Reactions

L-Cystine + Water → Pyruvic acid + Ammonia + Thiocysteine	details

Showing metabocard for Thiocysteine (HMDB0003585)

MOL for HMDB0003585 (Thiocysteine)

3D MOL for HMDB0003585 (Thiocysteine)

3D SDF for HMDB0003585 (Thiocysteine)

3D-SDF for HMDB0003585 (Thiocysteine)

PDB for HMDB0003585 (Thiocysteine)

3D PDB for HMDB0003585 (Thiocysteine)

SMILES for HMDB0003585 (Thiocysteine)

INCHI for HMDB0003585 (Thiocysteine)

Structure for HMDB0003585 (Thiocysteine)

3D Structure for HMDB0003585 (Thiocysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions