Cannabis Compound Database: Showing Compound Card for L-Cystine (CDB000129)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1)transporters (4) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:25:51 UTC

Updated at

2020-12-07 19:07:08 UTC

CannabisDB ID

CDB000129

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

L-Cystine

Description

Cystine is an oxidized dimeric form of cysteine, an amino acid. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. This organosulfur compound has the formula (SCH2CH(NH2) CO2H)2. It is a colorless solid that melts at 247-249 ¬∞C. It was discovered in 1810 by William Hyde Wollaston but was not recognized as being derived of proteins until it was isolated from the horn of a cow in 1899. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Cystine also functions in redox reactions. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions, is partially responsible for the formation of the gluten matrix in bread. Cystine is found in high concentrations in the cells of the immune system, skeletal and connective tissues, skin, digestive enzymes, and in hair. It is found largely withing nonreducing organelles within cells such as the Golgi, ER, lysosomes and vesicles while cysteine is found in the reducing environment of the cytoplasm and the extracellular space. Cystine is the preferred form of cysteine for the synthesis of glutathione (a tripeptide consisting of cysteine, glutamate and glycine) 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. Cystine naturally occurs as a deposit in the urine and can form a calculus (hard mineral formation) when deposited in the kidney. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc. Cystine is also found in Cannabis plants (PMID: 6991645 ).

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

240.0238

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

Physiological effect

Health effect:

Observation:

Acute seizures

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Essential amino acid

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000x-9000000000-ae0f516d71e6a49fe52f	2015-03-01	View Spectrum
GC-MS	L-Cystine, 4 TMS, GC-MS Spectrum	splash10-00kb-0950000000-a803bc05843192dd737d	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-00kb-0940000000-f82b905ef9e7c9e47552	Spectrum
GC-MS	L-Cystine, 4 TMS, GC-MS Spectrum	splash10-00di-9850000000-49b9a52a8387d6d6f272	Spectrum
GC-MS	L-Cystine, 4 TMS, GC-MS Spectrum	splash10-014j-1970000000-9576699202733d4fd7ed	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-00kb-0950000000-a803bc05843192dd737d	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-00di-9850000000-49b9a52a8387d6d6f272	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-014j-1970000000-9576699202733d4fd7ed	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-7cb336c3f272fd0fcd6b	Spectrum
GC-MS	L-Cystine, non-derivatized, GC-MS Spectrum	splash10-00kb-0920000000-1c414573da4bbe4a66dd	Spectrum
Predicted GC-MS	L-Cystine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0076-9400000000-211575093fd775db5d54	Spectrum
Predicted GC-MS	L-Cystine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0076-9112000000-ee49e3b674a4f8bb9ecd	Spectrum
Predicted GC-MS	L-Cystine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystine, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0890000000-51a32ee40240e45646bc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9700000000-4054924ddfb90f120e67	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9100000000-085d45702e61de0f8e4d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-9710000000-9321541af2ad89bd0478	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0090000000-041bfa55cb183f42f454	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-0190000000-3611e8b6715129842130	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0190000000-dbafdd64edad14af9281	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-0290000000-6b80d283287249ba4b87	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-000i-0390000000-c091ce388dfcbd339e3f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0079-0690000000-c808ac294a0bc182c5eb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0079-0970000000-36297b29c4ef45c658e3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-00dr-0940000000-a8c735a0f9082cfd7c7c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1920000000-9d55705325536cca5eb2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-00di-1910000000-cd18de2585913152e907	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-00di-1900000000-3118609f8682bee472c6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-00di-2900000000-213ccc3c067486ff9444	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-00di-3900000000-df68db23afd937a9a75d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-00di-4900000000-b46d26f57a194d2ff648	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-00di-6900000000-5535cccb24de733cada3	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-2970000000-b80e0aef184b74ce7a36	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00re-4910000000-a09277c5a6bfc432eb79	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xu-9600000000-0518bfcaab380952c123	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3590000000-aa667d3c092c5af3ae7f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-5910000000-122bd251359ca80b184c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9300000000-bbb14e684ff7c06e7916	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
B(0,+)-type amino acid transporter 1	SLC7A9	19q13.1	P82251	details
Cystine/glutamate transporter	SLC7A11	4q28-q32	Q9UPY5	details
Neutral amino acid transporter A	SLC1A4	2p15-p13	P43007	details
Monocarboxylate transporter 10	SLC16A10	6q21-q22	Q8TF71	details

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000192

DrugBank ID

DB00138

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

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

Transporters

Enzyme Details

1. B(0,+)-type amino acid transporter 1

General function:: Involved in transport
Specific function:: Involved in the high-affinity, sodium-independent transport of cystine and neutral and dibasic amino acids (system b(0,+)-like activity). Thought to be responsible for the high- affinity reabsorption of cystine in the kidney tubule
Gene Name:: SLC7A9
Uniprot ID:: P82251
Molecular weight:: 53480.8

Enzyme Details

2. Cystine/glutamate transporter

General function:: Involved in transport
Specific function:: Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name:: SLC7A11
Uniprot ID:: Q9UPY5
Molecular weight:: 55422.44

Enzyme Details

3. Neutral amino acid transporter A

General function:: Involved in sodium:dicarboxylate symporter activity
Specific function:: Transporter for alanine, serine, cysteine, and threonine. Exhibits sodium dependence
Gene Name:: SLC1A4
Uniprot ID:: P43007
Molecular weight:: 55722.5

Enzyme Details

4. Monocarboxylate transporter 10

General function:: Involved in transmembrane transport
Specific function:: Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:: SLC16A10
Uniprot ID:: Q8TF71
Molecular weight:: 55492.1

Showing Compound Card for L-Cystine (CDB000129)

Structure for CDB000129 (L-Cystine)

Enzymes

Transporters