Bovine Metabolome Database: Showing metabocard for L-Cystine (BMDB0000192)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:32 UTC

Update Date

2020-06-04 21:10:52 UTC

BMDB ID

BMDB0000192

Secondary Accession Numbers

BMDB00192

Metabolite Identification

Common Name

L-Cystine

Description

Cystine, also known as L-dicysteine or E921, 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. Cystine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Cystine exists in all living species, ranging from bacteria to humans. Cystine has been found to be associated with several diseases known as molybdenum cofactor deficiency, schizophrenia, parkinson's disease, and colorectal cancer; also cystine has been linked to the inborn metabolic disorders including fumarase deficiency.

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

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	260.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.19 mg/mL	Not Available
LogP	-5.08	CHMELIK,J ET AL. (1991)

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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00kb-0950000000-a803bc05843192dd737d	View in 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	View in 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	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014j-1970000000-9576699202733d4fd7ed	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0950000000-a803bc05843192dd737d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9850000000-49b9a52a8387d6d6f272	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014j-1970000000-9576699202733d4fd7ed	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0930000000-7cb336c3f272fd0fcd6b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0920000000-1c414573da4bbe4a66dd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-9400000000-211575093fd775db5d54	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0076-9112000000-ee49e3b674a4f8bb9ecd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0890000000-51a32ee40240e45646bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9700000000-4054924ddfb90f120e67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9100000000-085d45702e61de0f8e4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-9710000000-9321541af2ad89bd0478	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0090000000-041bfa55cb183f42f454	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0190000000-3611e8b6715129842130	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0190000000-dbafdd64edad14af9281	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0290000000-6b80d283287249ba4b87	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-000i-0390000000-c091ce388dfcbd339e3f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0079-0690000000-c808ac294a0bc182c5eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0079-0970000000-36297b29c4ef45c658e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-00dr-0940000000-a8c735a0f9082cfd7c7c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1920000000-9d55705325536cca5eb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1910000000-cd18de2585913152e907	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-00di-1900000000-3118609f8682bee472c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-00di-2900000000-213ccc3c067486ff9444	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-00di-3900000000-df68db23afd937a9a75d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-00di-4900000000-b46d26f57a194d2ff648	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-00di-6900000000-5535cccb24de733cada3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-2970000000-b80e0aef184b74ce7a36	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00re-4910000000-a09277c5a6bfc432eb79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xu-9600000000-0518bfcaab380952c123	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3590000000-aa667d3c092c5af3ae7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-5910000000-122bd251359ca80b184c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9300000000-bbb14e684ff7c06e7916	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-000x-9000000000-ae0f516d71e6a49fe52f	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

All Tissues
Liver
Mammary Gland
Milk
Placenta
Semen
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Milk	Detected and Quantified	1123.596 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1123.596 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1123.596 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1123.596 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1081.981 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1081.981 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1081.981 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details
Testis	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000192

DrugBank ID

DB00138

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16283

References

Synthesis Reference

Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry (2002), 67(24), 8625-8630.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for L-Cystine (BMDB0000192)

Structure for BMDB0000192 (L-Cystine)