Cystine

Details

• Internal ID: a3f96374-83e7-4387-a3b8-f46b580c1534
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Cysteine and derivatives > L-cysteine-S-conjugates
• IUPAC Name: (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
• SMILES (Canonical): C(C(C(=O)O)N)SSCC(C(=O)O)N
• SMILES (Isomeric): C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)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
• InChI Key: LEVWYRKDKASIDU-IMJSIDKUSA-N
• Popularity: 24,814 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₂N₂O₄S₂
• Molecular Weight: 240.30 g/mol
• Exact Mass: 240.02384922 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: -6.30
• Atomic LogP (AlogP): -0.81
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 56-89-3
• cystine
• L-Cystin
• L-Dicysteine
• Cysteine disulfide
• Cystin
• beta,beta'-Dithiodialanine
• L-Cysteine disulfide
• 1-Cystine
• 3,3'-Dithiodialanine
• Cystine, L-
• Dicysteine
• Cystine (L)-
• Cystine acid
• (H-Cys-OH)2
• Alanine, 3,3'-dithiodi-
• Alanine, 3,3'-dithiobis-
• beta,beta'-Dithioalanine, L-
• L-Alanine, 3,3'-dithiobis-
• 3,3'-Dithiobis(2-aminopropanoic acid)
• Cystine (VAN)
• Cystine [USAN]
• Cystin (VAN)
• L-(-)-Cystine
• (-)-Cystine
• Gelucystine
• CCRIS 5822
• L-alpha-Diamino-beta-dithiolactic acid
• Cystine,d
• Bis(beta-amino-beta-carboxyethyl)disulfide
• UNII-48TCX9A1VT
• 3,3'-Dithiobis-L-alanine
• EINECS 200-296-3
• (R-(R*,R*))-3,3'-Dithiobis(2-aminopropanoic acid)
• 48TCX9A1VT
• NSC 13203
• beta,beta'-Diamino-beta,beta'-dicarboxydiethyl disulfide
• BRN 1728094
• DTXSID2046418
• CHEBI:16283
• AI3-09064
• beta,beta'-Diamino-beta,beta'-dicarboxydiethyldisulfide
• Cystine [USAN:INN]
• (2R,2'R)-3,3'-disulfanediylbis(2-aminopropanoic acid)
• 3,3'-Dithiobis(2-aminopropanoic acid), (R-(R*,R*))-
• Propanoic acid, 3,3'-dithiobis(2-amino-, (R-(R*,R*))-
• NSC-13203
• S-CYSTEINYL CYSTEINE
• Bis(beta-amino-beta-carboxyethyl) disulfide
• DTXCID0026418
• EC 200-296-3
• (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
• 4-04-00-03155 (Beilstein Handbook Reference)
• Cystine (L-Cystine)
• C6H12N2O4S2
• E921
• CYSTINE (MART.)
• CYSTINE [MART.]
• CYSTINE (USP-RS)
• CYSTINE [USP-RS]
• (R,R)-3,3'-dithiobis(2-aminopropanoic acid)
• S-(((R)-2-amino-2-carboxyethyl)thio)cysteine
• cistina
• Zystin
• cystin-
• CYSTINE (EP MONOGRAPH)
• CYSTINE [EP MONOGRAPH]
• 3,3-DISULFANEDIYLBIS((2R)-2-AMINOPROPANOIC ACID)
• 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid
• L-Cystin-
• alpha-Diamino-beta-dithiolactic acid
• (R-(R*,R*))-3,3'-Dithiobis
• [R-(R*,R*)]-3,3'-Dithiobis
• MFCD00064228
• L Cystine
• (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
• CAS-56-89-3
• 2079930-29-1
• TYROSINE IMPURITY C (EP IMPURITY)
• TYROSINE IMPURITY C [EP IMPURITY]
• (R,R)-3,3'-Dithiobis(2-aminopropionicacid)
• ACETYLCYSTEINE IMPURITY A (EP IMPURITY)
• ACETYLCYSTEINE IMPURITY A [EP IMPURITY]
• 24645-67-8
• [R-(R*,R*)]-3,3'-dithiobis[2-aminopropanoic acid]
• cystinum
• DTXSID50859005
• C6-H12-N2-O4-S2
• NCGC00164531-01
• IYY
• 3,3'-Dithiobis
• b,b'-Dithiodialanine
• L-Cystine (9CI)
• Cystine (USAN/INN)
• L-Cystine (JP17)
• CYSTINE [VANDF]
• CYSTINE [INCI]
• CYSTINE [INN]
• CYSTINE [MI]
• L-CYSTINE [FCC]
• L-CYSTINE [JAN]
• Cystine, L- (8CI)
• CYSTINE [WHO-DD]
• bmse000035
• D0V1CP
• (2R)-2-amino-3-[[(2R)-2-amino-2-carboxy-ethyl]disulfanyl]propanoic acid
• beta,beta'-Dithiobisalanine
• SCHEMBL10226
• L-Cystine, non-animal source
• CHEMBL590540
• GTPL5413
• (H-Cys-OH)2 (Disulfide bond)
• DTXCID60210087
• HY-N0394
• Tox21_112162
• CCG-36355
• L-Cystine, >=99.7% (TLC)
• s4808
• Bis(b-amino-b-carboxyethyl) disulfide
• Cystine, NIST(R) SRM(R) 143d
• AKOS015898645
• Tox21_112162_1
• AM81644
• DB00138
• (2R)-2-azanyl-3-[[(2R)-2-azanyl-3-oxidanyl-3-oxidanylidene-propyl]disulfanyl]propanoic acid
• Bis(b-amino-beta-carboxyethyl) disulfide
• NCGC00166006-01
• NCGC00166006-02
• AC-11189
• AS-12654
• D(+)-3,3'-Dithiobis(2-aminopropanoate
• L-Cystine, >=98% (TLC), crystalline
• L-Cystine, BioUltra, >=99.5% (T)
• LS-59051
• L-Cystine, SAJ special grade, >=99.0%
• L-Cystine, Vetec(TM) reagent grade, 98%
• ACETYLCYSTEINE IMPURITY A (L-CYSTINE)
• b,b'-Diamino-b,b'-dicarboxydiethyl disulfide
• CS-0008930
• D(+)-3,3'-Dithiobis(2-aminopropanoic acid
• (R,R)-3,3'-Dithiobis(2-aminopropionic Acid)
• C00491
• D03636
• EN300-174654
• M06021
• Q408626
• 3,3'-Disulfanediylbis((2R)-2-aminopropanoic acid)
• 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoate
• 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate
• L-Cystine, certified reference material, TraceCERT(R)
• 3,3'-dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid
• Cystine, European Pharmacopoeia (EP) Reference Standard
• Z1269145231
• 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate
• 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid
• DD82F461-3F8F-4624-9E2C-0272A9FA79ED
• Cystine, United States Pharmacopeia (USP) Reference Standard
• L-Cystine, Cell Culture Reagent (H-L-Cys(1)-OH.H-L-Cys(1)-OH)
• L-Cystine, Pharmaceutical Secondary Standard; Certified Reference Material
• L-Cystine, produced by Wacker Chemie AG, Burghausen, Germany, >=98.5%
• L-Cystine, from non-animal source, meets EP testing specifications, suitable for cell culture, 98.5-101.0%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7278	72.78%
Caco-2	-	0.8669	86.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5274	52.74%
OATP2B1 inhibitior	-	0.8493	84.93%
OATP1B1 inhibitior	+	0.9692	96.92%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9338	93.38%
P-glycoprotein inhibitior	-	0.9584	95.84%
P-glycoprotein substrate	-	0.9916	99.16%
CYP3A4 substrate	-	0.7991	79.91%
CYP2C9 substrate	-	0.6009	60.09%
CYP2D6 substrate	-	0.8172	81.72%
CYP3A4 inhibition	-	0.6103	61.03%
CYP2C9 inhibition	-	0.8968	89.68%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9149	91.49%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	-	0.9893	98.93%
CYP inhibitory promiscuity	-	0.9950	99.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5300	53.00%
Carcinogenicity (trinary)	Non-required	0.6211	62.11%
Eye corrosion	-	0.9583	95.83%
Eye irritation	-	0.8217	82.17%
Skin irritation	-	0.8722	87.22%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	+	0.7022	70.22%
Human Ether-a-go-go-Related Gene inhibition	-	0.7035	70.35%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	-	0.8556	85.56%
Reproductive toxicity	-	0.6889	68.89%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.7373	73.73%
Acute Oral Toxicity (c)	III	0.6711	67.11%
Estrogen receptor binding	-	0.7895	78.95%
Androgen receptor binding	-	0.6615	66.15%
Thyroid receptor binding	-	0.7675	76.75%
Glucocorticoid receptor binding	-	0.5196	51.96%
Aromatase binding	-	0.8516	85.16%
PPAR gamma	-	0.5460	54.60%
Honey bee toxicity	-	0.9204	92.04%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	+	0.6586	65.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.20%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.69%	96.09%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.93%	92.29%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.71%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.15%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	82.63%	90.17%

Plants that contains it

• Allium sativum
• Antirrhinum majus
• Arabidopsis thaliana
• Cannabis sativa
• Glycine max
• Laburnum anagyroidis
• Panax ginseng
• Psophocarpus tetragonolobus
• Senna obtusifolia
• Thymus transcaucasicus

Cross-Links

• PubChem: 67678
• NPASS: NPC185755
• ChEMBL: CHEMBL590540
• LOTUS: LTS0192149
• wikiData: Q408626