Livestock Metabolome Database: Showing metabocard for L-Cystine (LMDB00086)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:03 UTC

Update Date

2016-07-20 20:23:20 UTC

Lmdb

LMDB00086

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-Cystine

Description

Cystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. Cystine is found in high concentrations in the cells of the immune system, skeletal and connective tissues, skin, digestive enzymes, and in hair. Hair and skin are 10-14% cystine. Cystine is the preferred form of cysteine for the synthesis of glutathione in cells involved in the immune function including macrophages and astrocytes. Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand. (http://en.wikipedia.org/wiki/Cystine).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)	ChEBI
(R-(R,r))-3,3'-dithiobis(2-aminopropanoic acid)	ChEBI
3,3'-Dithiobis-L-alanine	ChEBI
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide	ChEBI
beta,Beta'-dithiodialanine	ChEBI
Bis(beta-amino-beta-carboxyethyl) disulfide	ChEBI
e921	ChEBI
L-alpha-Diamino-beta-dithiolactic acid	ChEBI
L-Dicysteine	ChEBI
Oxidized L-cysteine	ChEBI
(R,R)-3,3'-Dithiobis(2-aminopropanoate)	Generator
(R-(R,r))-3,3'-dithiobis(2-aminopropanoate)	Generator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide	Generator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide	Generator
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide	Generator
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide	Generator
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide	Generator
b,Beta'-dithiodialanine	Generator
Β,beta'-dithiodialanine	Generator
Bis(b-amino-b-carboxyethyl) disulfide	Generator
Bis(b-amino-b-carboxyethyl) disulphide	Generator
Bis(beta-amino-beta-carboxyethyl) disulphide	Generator
Bis(β-amino-β-carboxyethyl) disulfide	Generator
Bis(β-amino-β-carboxyethyl) disulphide	Generator
L-a-Diamino-b-dithiolactate	Generator
L-a-Diamino-b-dithiolactic acid	Generator
L-alpha-Diamino-beta-dithiolactate	Generator
L-Α-diamino-β-dithiolactate	Generator
L-Α-diamino-β-dithiolactic acid	Generator
(-)-Cystine	HMDB
(R-(R,r))-3,3'-dithiobis	HMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate	HMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid	HMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate	HMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid	HMDB
3,3'-Dithiobis	HMDB
3,3'-Dithiobis[2-amino-[R-(r,r)]-propanoate	HMDB
3,3'-Dithiobis[2-amino-[R-(r,r)]-propanoic acid	HMDB
3,3'-Dithiodialanine	HMDB
b,B'-diamino-b,b'-dicarboxydiethyl disulfide	HMDB
b,B'-dithiodialanine	HMDB
beta,Beta'-dithiobisalanine	HMDB
Bis(b-amino-beta-carboxyethyl) disulfide	HMDB
Cysteine disulfide	HMDB
Cystin	HMDB
Cystine	HMDB
Cystine acid	HMDB
D(+)-3,3'-Dithiobis(2-aminopropanoate	HMDB
D(+)-3,3'-Dithiobis(2-aminopropanoic acid	HMDB
Dicysteine	HMDB
Gelucystine	HMDB
L-(-)-Cystine	HMDB
L-Cysteine disulfide	HMDB
L-Cystin	HMDB
[R-(R,r)]-3,3'-dithiobis	HMDB
L Cystine	HMDB
Copper cystinate	HMDB
L-Cystine	KEGG

Chemical Formula

C₆H₁₂N₂O₄S₂

Average Molecular Weight

240.3

Monoisotopic Molecular Weight

240.023848262

IUPAC Name

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

Traditional Name

L-cystine

CAS Registry Number

56-89-3

SMILES

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

InChI Identifier

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

InChI Key

LEVWYRKDKASIDU-IMJSIDKUSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	-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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Plasma	Detected and Quantified	15.22 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	17.07 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	17.83 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	23.96 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	23 +/- 2-18+/-2 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	36 +/- 4-38+/-11 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	41 +/- 8-28+/-4 uM	Not Available	Porcine	22513987	details