U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H12N2O4S2
Molecular Weight 240.3
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYSTINE

SMILES

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

InChI

InChIKey=LEVWYRKDKASIDU-IMJSIDKUSA-N
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

HIDE SMILES / InChI

Molecular Formula C6H12N2O4S2
Molecular Weight 240.3
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7276953 | https://www.ncbi.nlm.nih.gov/pubmed/27306219 | https://www.ncbi.nlm.nih.gov/pubmed/28297659

Cystine is the oxidized dimer form of the amino acid cysteine. Cystine serves two biological functions, a site of redox reactions and a mechanical linkage that allows proteins to retain their 3-dimensional structure. It is common in many foods such as eggs, meat, dairy products, and whole grains as well as skin, horns and hair. Human hair and skin contain approximately 10–14% cystine by mass. Cysteine supplements are sometimes marketed as anti-aging products with claims of improved skin elasticity. Cysteine is more easily absorbed by the body than cystine, so most supplements contain cysteine rather than cystine. N-acetyl-cysteine (NAC) is better absorbed than other cysteine or cystine supplements.

Originator

Sources: Journal of the American Chemical Society Volume 19, Issue 5, Pages382-4, Journal , 1897

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Infrared analysis of urinary calculi by a single reflection accessory and a neural network interpretation algorithm.
2001
Capture and identification of folding intermediates of cystinyl proteins by cyanylation and mass spectrometry.
2001
Blood glutathione and cysteine concentrations in twin children.
2001 Apr
Histological and histochemical observations in the stomach of the Senegal sole, Solea senegalensis.
2001 Apr
Determination by liquid chromatography of free and total cysteine in human urine in the form of its S-quinolinium derivative.
2001 Apr 13
xCt cystine transporter expression in HEK293 cells: pharmacology and localization.
2001 Apr 20
Hounsfield unit density in the determination of urinary stone composition.
2001 Aug
An efficient refolding method for the preparation of recombinant human prethrombin-2 and characterization of the recombinant-derived alpha-thrombin.
2001 Aug
Urinary sulfur compounds in Down syndrome.
2001 Aug
Solid phase assay of urine cystine supersaturation in the presence of cystine binding drugs.
2001 Aug
Identification and characterization of a new mammalian glutaredoxin (thioltransferase), Grx2.
2001 Aug 10
The activation of dopamine D4 receptors inhibits oxidative stress-induced nerve cell death.
2001 Aug 15
Location and mechanism of alpha 2,6-sialyltransferase dimer formation. Role of cysteine residues in enzyme dimerization, localization, activity, and processing.
2001 Aug 3
Solution structure of the satiety factor, CART, reveals new functionality of a well-known fold.
2001 Aug 7
A DNA polymerase with specificity for five base pairs.
2001 Feb 28
The amino acid transport system b(o,+) and cystinuria.
2001 Jan-Mar
Thermosipho geolei sp. nov., a thermophilic bacterium isolated from a continental petroleum reservoir in Western Siberia.
2001 Jul
Laminar distribution of nicotinic receptor subtypes in cortical regions in schizophrenia.
2001 Jul
Medical and surgical therapy of the cystine stone patient.
2001 Jul
Metabolism of S-nitrosoglutathione by endothelial cells.
2001 Jul
Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells.
2001 Jul 1
Role of the cystine-knot motif at the C-terminus of rat mucin protein Muc2 in dimer formation and secretion.
2001 Jul 1
Hyperglycemia in diabetic rats reduces the glutathione content in the aortic tissue.
2001 Jul 20
Cystinuria in the dog: clinical studies during 14 years of medical treatment.
2001 Jul-Aug
Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide.
2001 Jul-Aug
Configuration and racemization determination of cysteine residues in peptides by chiral derivatization and HPLC: application to oxytocin peptides.
2001 Jun
Effect of fudosteine, a new cysteine derivative, on mucociliary transport.
2001 Jun
Estimation of the total sulfur amino acid requirement and the effect of betaine in diets deficient in total sulfur amino acids for the weanling pig.
2001 Jun
Partial restoration of lutropin activity by an intersubunit disulfide bond: implications for structure/function studies.
2001 Jun
How does hexachlorobenzene treatment affect liver uroporphyrinogen decarboxylase?
2001 Jun
The molecular bases of cystinuria and lysinuric protein intolerance.
2001 Jun
Cystine calculi in children: the results of a metabolic evaluation and response to medical therapy.
2001 Jun
Self-assembling, cystine-derived, fused nanotubes based on spirane architecture: design, synthesis, and crystal structure of cystinospiranes.
2001 Jun 20
Monitoring of the subtraction process in solid-phase representational difference analysis: characterization of a candidate drug.
2001 Jun 27
Human cystine/glutamate transporter: cDNA cloning and upregulation by oxidative stress in glioma cells.
2001 Jun 6
Folding screening assayed by proteolysis: application to various cystine deletion mutants of vascular endothelial growth factor.
2001 Mar
Role of stone analysis in metabolic evaluation and medical treatment of nephrolithiasis.
2001 Mar
Molecular cloning of preproinsulin cDNAs from several osteoglossomorphs and a cyprinid.
2001 Mar 28
[Leber's hereditary optic neuropathy].
2001 Mar-Apr
Evaluation of urinary carnitine and taurine excretion in 5 cystinuric dogs with carnitine and taurine deficiency.
2001 Mar-Apr
Extracorporeal shock wave lithotripsy in children. Efficacy, complications and long-term follow-up.
2001 May
A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid.
2001 May
The metabolism of sulphur in relation to the biochemistry of cystine and cysteine: its fundamental importance in biology. A cyclic interchange between their mono- and di-sulphides is the unique reaction creating life and intelligence.
2001 May
Energy utilization of low-protein diets in growing pigs.
2001 May
Synthetic peptides derived from the beta2-beta3 loop of Raphanus sativus antifungal protein 2 that mimic the active site.
2001 May
Evolution and classification of cystine knot-containing hormones and related extracellular signaling molecules.
2001 May
Human cystinuria-related transporter: localization and functional characterization.
2001 May
Design of Gram-negative selective antimicrobial peptides.
2001 May 15
Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis.
2001 May 18
Pediatric urolithiasis in Armenia: a study of 198 patients observed from 1991 to 1999.
2001 Sep
Patents

Sample Use Guides

The subjects in the C/T group were orally administered an amino acid supplement, which contained 700 mg cystine and 280 mg theanine (total weight, 1.7 g; Ajinomoto, Tokyo, Japan), once a day starting 1 week before and ending at the same time as the administration of S-1 (a total of 35 days)
Route of Administration: Oral
200,000 hTERT-HME cell were plated in 6-well plates and switched to cystine-deprived media for 12 hr prior to FACS analysis. CMDCFDA and C11-BODIPY581/591 (Molecular Probes; Thermo Fisher) were used to detect total and lipid ROS, respectively. Following deprivation of cystine for 12 hr, cells were washed with PBS, loaded with either CMDCFDA (10 mM) or C11 BODIPY (2 mM) in DPBS for 30 min, trypsinized with 0.25% Trypsin-EDTA, resuspended inPBSwith1%FBS, and analyzed using an AttuneNxT flow cytometer (Thermo Fisher). Dyes were excited using a blue 488-nm laser, and emission was recorded on BL1 (530/30) for a minimum of 5,000 cells per sample.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:04:02 UTC 2023
Edited
by admin
on Sat Dec 16 18:04:02 UTC 2023
Record UNII
48TCX9A1VT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYSTINE
EP   INCI   INN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   INCI   USAN  
Official Name English
CYSTINE [EP MONOGRAPH]
Common Name English
ACETYLCYSTEINE IMPURITY A [EP IMPURITY]
Common Name English
S-CYSTEINYL CYSTEINE
Systematic Name English
CYSTINE, L-
Common Name English
L-CYSTINE
FCC  
Systematic Name English
CYSTINE [INCI]
Common Name English
TYROSINE IMPURITY C [EP IMPURITY]
Common Name English
CYSTINE [MI]
Common Name English
3,3-DISULFANEDIYLBIS((2R)-2-AMINOPROPANOIC ACID)
Systematic Name English
L-CYSTINE [FCC]
Common Name English
Cystine [WHO-DD]
Common Name English
cystine [INN]
Common Name English
NSC-13203
Code English
L-CYSTINE [JAN]
Common Name English
CYSTINE [USP-RS]
Common Name English
CYSTINE [USAN]
Common Name English
CYSTINE [VANDF]
Common Name English
CYSTINE [MART.]
Common Name English
Classification Tree Code System Code
LOINC 27027-2
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
LOINC 22687-8
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LOINC 13371-0
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LOINC 12469-3
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DSLD 2409 (Number of products:212)
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LOINC 34278-2
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DSLD 76 (Number of products:12)
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LOINC 2180-8
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NCI_THESAURUS C29596
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LOINC 26843-3
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LOINC 25894-7
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LOINC 32169-5
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LOINC 2179-0
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LOINC 14686-0
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LOINC 33872-3
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LOINC 10969-4
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LOINC 16709-8
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LOINC 13966-7
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LOINC 44312-7
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LOINC 53080-8
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LOINC 27350-8
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LOINC 21056-7
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LOINC 2175-8
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LOINC 32237-0
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LOINC 32238-8
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LOINC 30065-7
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LOINC 32138-0
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LOINC 2177-4
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LOINC 9644-6
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CFR 21 CFR 172.320
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LOINC 56677-8
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LOINC 16711-4
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LOINC 22728-0
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LOINC 2178-2
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LOINC 26962-1
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LOINC 13725-7
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LOINC 2176-6
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LOINC 22672-0
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LOINC 22653-0
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LOINC 13394-2
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Code System Code Type Description
MESH
D003553
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
RS_ITEM_NUM
1161586
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
DRUG BANK
DB00138
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
EVMPD
SUB01541MIG
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID2046418
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
WIKIPEDIA
CYSTINE
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
DRUG CENTRAL
4130
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
NSC
13203
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
MERCK INDEX
m4049
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY Merck Index
CHEBI
16283
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
RXCUI
3036
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PRIMARY RxNorm
SMS_ID
100000091082
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
FDA UNII
48TCX9A1VT
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
DAILYMED
48TCX9A1VT
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
NCI_THESAURUS
C29610
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
CHEBI
17376
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
PUBCHEM
67678
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-296-3
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PRIMARY
EVMPD
SUB41569
Created by admin on Sat Dec 16 18:04:03 UTC 2023 , Edited by admin on Sat Dec 16 18:04:03 UTC 2023
PRIMARY
CHEBI
35491
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PRIMARY
CAS
56-89-3
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PRIMARY
CHEBI
50058
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PRIMARY
ChEMBL
CHEMBL590540
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PRIMARY
INN
7922
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PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
INHIBITOR OF AGGREGATION->TARGET
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Natural substrate for transporter responsible for enhancing the synthesis of GSH by bringing cystine into cell. Inhibition leads ferroptosis.
INHIBITOR -> TARGET
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY