L-Cystine (YMDB00886)

Identification

YMDB ID

YMDB00886

Name

L-Cystine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Cystine is an oxidized dimeric form of the amino acid cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions is partially responsible for the formation of the gluten matrix in bread.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-Cystine
(R-(R*,R*))-3,3'-Dithiobis
[R-(R*,R*)]-3,3'-Dithiobis
2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate
2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid
3,3'-Dithiobis
3,3'-dithiobis-L-Alanine
3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoate
3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid
3,3'-Dithiodialanine
b,b'-Diamino-b,b'-dicarboxydiethyl disulfide
b,b'-Dithiodialanine
beta,beta'-Dithiobisalanine
beta,beta'-Dithiodialanine
Bis(b-amino-b-carboxyethyl) disulfide
Bis(b-amino-beta-carboxyethyl) disulfide
Cysteine disulfide
Cystin
Cystine
Cystine acid
D(+)-3,3'-Dithiobis(2-aminopropanoate
D(+)-3,3'-Dithiobis(2-aminopropanoic acid
Dicysteine
Gelucystine
L-(-)-Cystine
L-Cysteine disulfide
L-Cystin
l-Cystine
Oxidized L-cysteine
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide
Bis(beta-amino-beta-carboxyethyl) disulfide
e921
L-alpha-Diamino-beta-dithiolactic acid
L-Dicysteine
(R,R)-3,3'-Dithiobis(2-aminopropanoate)
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide
b,Beta'-dithiodialanine
Β,beta'-dithiodialanine
Bis(b-amino-b-carboxyethyl) disulphide
Bis(beta-amino-beta-carboxyethyl) disulphide
Bis(β-amino-β-carboxyethyl) disulfide
Bis(β-amino-β-carboxyethyl) disulphide
L-a-Diamino-b-dithiolactate
L-a-Diamino-b-dithiolactic acid
L-alpha-Diamino-beta-dithiolactate
L-Α-diamino-β-dithiolactate
L-Α-diamino-β-dithiolactic acid
L Cystine
Copper cystinate

CAS number

56-89-3

Weight

Average: 240.3
Monoisotopic: 240.023848262

InChI Key

LEVWYRKDKASIDU-IMJSIDKUSA-N

InChI

InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

IUPAC Name

(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

Traditional IUPAC Name

L-cystine

Chemical Formula

C₆H₁₂N₂O₄S₂

SMILES

[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])SSC([H])([H])[C@]([H])(N([H])[H])C(=O)O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-cysteine-S-conjugates

Alternative Parents

Substituents

L-cysteine-s-conjugate
Alpha-amino acid
L-alpha-amino acid
Dicarboxylic acid or derivatives
Organic disulfide
Dialkyldisulfide
Amino acid
Sulfenyl compound
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:16283 )
L-cysteine derivative (CHEBI:16283 )
cystine (CHEBI:16283 )

Physical Properties

State

Solid

Charge

Melting point

260.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.19 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-5.08 [CHMELIK,J ET AL. (1991)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	16.8 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-5.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.87 m³·mol⁻¹	ChemAxon
Polarizability	22.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

vacuole
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Cysteine and methionine metabolism

ec00270

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00kb-0950000000-a803bc05843192dd737d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00kb-0940000000-f82b905ef9e7c9e47552	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9850000000-49b9a52a8387d6d6f272	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014j-1970000000-9576699202733d4fd7ed	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0950000000-a803bc05843192dd737d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9850000000-49b9a52a8387d6d6f272	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014j-1970000000-9576699202733d4fd7ed	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0930000000-7cb336c3f272fd0fcd6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0920000000-1c414573da4bbe4a66dd	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-9400000000-211575093fd775db5d54	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0076-9112000000-ee49e3b674a4f8bb9ecd	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0890000000-51a32ee40240e45646bc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9700000000-4054924ddfb90f120e67	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9100000000-085d45702e61de0f8e4d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-9710000000-9321541af2ad89bd0478	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0090000000-041bfa55cb183f42f454	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0190000000-3611e8b6715129842130	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0190000000-dbafdd64edad14af9281	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0290000000-6b80d283287249ba4b87	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-000i-0390000000-c091ce388dfcbd339e3f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0079-0690000000-c808ac294a0bc182c5eb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0079-0970000000-36297b29c4ef45c658e3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-00dr-0940000000-a8c735a0f9082cfd7c7c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1920000000-9d55705325536cca5eb2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1910000000-cd18de2585913152e907	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-00di-1900000000-3118609f8682bee472c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-00di-2900000000-213ccc3c067486ff9444	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-00di-3900000000-df68db23afd937a9a75d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-00di-4900000000-b46d26f57a194d2ff648	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-00di-6900000000-5535cccb24de733cada3	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-2970000000-b80e0aef184b74ce7a36	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00re-4910000000-a09277c5a6bfc432eb79	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xu-9600000000-0518bfcaab380952c123	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3590000000-aa667d3c092c5af3ae7f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-5910000000-122bd251359ca80b184c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9300000000-bbb14e684ff7c06e7916	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-000x-9000000000-ae0f516d71e6a49fe52f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16283
HMDB ID	HMDB00192
Pubchem Compound ID	67678
Kegg ID	C00491
ChemSpider ID	60997
FOODB ID	FDB012672
Wikipedia	Cystine
BioCyc ID	CYSTINE

Transporters

Protein Details

1. Cystine transporter

General function:: Involved in L-cystine transmembrane transporter activity
Specific function:: Transport cystine out of vacuoles/endodomes
Gene Name:: ERS1
Uniprot ID:: P17261
Molecular weight:: 30116.0

Structure for #<Compound:0xa85200f0>

Transporters