MiMeDB: Showing metabocard for D-Cystine (MMDBc0033156)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:36:59 UTC

Update Date

2022-08-31 22:26:49 UTC

Metabolite ID

MMDBc0033156

Metabolite Identification

Common Name

D-Cystine

Description

Cystine is an oxidized dimeric form of the amino acid cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions is partially responsible for the formation of the gluten matrix in bread.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222382D          

 14 13  0  0  1  0            999 V2000
    2.5076    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -0.2350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5076    1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -1.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221   -0.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.1775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4937   -1.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    0.1775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082    0.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  1  6  0  0  0
  2  6  1  0  0  0  0
  5  6  1  0  0  0  0
  7  1  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  6  0  0  0
  9 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14  8  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033156

> <DATABASE_NAME>
MIME

> <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-/m1/s1

> <INCHI_KEY>
LEVWYRKDKASIDU-QWWZWVQMSA-N

> <FORMULA>
C6H12N2O4S2

> <MOLECULAR_WEIGHT>
240.3

> <EXACT_MASS>
240.023848262

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.42620638472798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-{[(2S)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

> <ALOGPS_LOGP>
-3.16

> <JCHEM_LOGP>
-5.897687960059564

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.267408279723485

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.55642310919034

> <JCHEM_PKA_STRONGEST_BASIC>
9.34214059674757

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
54.87179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-cystine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.681   0.331   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.347  -0.439   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.681   1.871   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.347  -1.979   0.000  0.00  0.00           N+0
HETATM    5  S   UNK     0       0.680  -0.439   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       2.014   0.331   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.015  -0.439   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.655  -0.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.321   0.331   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.655  -1.979   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.321   1.871   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0      -0.654   0.331   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      -1.988  -0.439   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.989   0.331   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    6   12                                                       
CONECT    6    2    5                                                       
CONECT    7    1                                                            
CONECT    8    9   10   14                                                  
CONECT    9    8   11   13                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12   13    5                                                       
CONECT   13    9   12                                                       
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
(2S,2's)-3,3'-Dithiobis(2-aminopropanoic acid)	ChEBI
Cystine D-form	ChEBI
(2S,2's)-3,3'-Dithiobis(2-aminopropanoate)	Generator
Copper cystinate	MeSH
L Cystine	MeSH
L-Cystine	MeSH
Cystine	MeSH

Molecular Formula

C₆H₁₂N₂O₄S₂

Average Mass

240.3

Monoisotopic Mass

240.023848262

IUPAC Name

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

Traditional Name

D-cystine

CAS Registry Number

349-46-2

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-/m1/s1

InChI Key

LEVWYRKDKASIDU-QWWZWVQMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
D-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

cystine (CHEBI:35494 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	16.8 g/L	ALOGPS
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	22.43 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-9400000000-211575093fd775db5d54	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-2970000000-b80e0aef184b74ce7a36	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00re-4910000000-a09277c5a6bfc432eb79	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xu-9600000000-0518bfcaab380952c123	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3590000000-aa667d3c092c5af3ae7f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-5910000000-122bd251359ca80b184c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9300000000-bbb14e684ff7c06e7916	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cystine

METLIN ID

Not Available

PubChem Compound

6857538

PDB ID

Not Available

ChEBI ID

35494

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for D-Cystine (MMDBc0033156)

MOL for #<Metabolite:0x00007feccc31f5b8>

3D MOL for #<Metabolite:0x00007feccc31f5b8>

3D SDF for #<Metabolite:0x00007feccc31f5b8>

3D-SDF for #<Metabolite:0x00007feccc31f5b8>

PDB for #<Metabolite:0x00007feccc31f5b8>

3D PDB for #<Metabolite:0x00007feccc31f5b8>

SMILES for #<Metabolite:0x00007feccc31f5b8>

INCHI for #<Metabolite:0x00007feccc31f5b8>

Structure for #<Metabolite:0x00007feccc31f5b8>

3D Structure for #<Metabolite:0x00007feccc31f5b8>