NP-MRD: Showing NP-Card for cystine (NP0266538)

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Record Information

Version

2.0

Created at

2022-09-08 10:54:41 UTC

Updated at

2023-04-28 19:00:54 UTC

NP-MRD ID

NP0266538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cystine

Description

cystine is found in Antirrhinum majus, Claviceps purpurea and Glycine max. cystine was first documented in 2008 (PMID: 18608550).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305221920212D          

 14 13  0  0  0  0            999 V2000
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CSSCC(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)

> <INCHI_KEY>
LEVWYRKDKASIDU-UHFFFAOYSA-N

> <FORMULA>
C6H12N2O4S2

> <MOLECULAR_WEIGHT>
240.3

> <EXACT_MASS>
240.023848262

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.782797923268646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-[(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>
1.5564231091903382

> <JCHEM_PKA_STRONGEST_BASIC>
9.342140596747571

> <JCHEM_POLAR_SURFACE_AREA>
126.64

> <JCHEM_REFRACTIVITY>
54.87180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cystine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.185  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.518  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.852  -1.334   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.850  -2.874   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      10.518   0.976   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       1.183  -1.334   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.516   0.976   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      13.186  -0.564   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.852  -2.874   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       6.517  -1.334   0.000  0.00  0.00           S+0
HETATM   14  S   UNK     0       7.851  -0.564   0.000  0.00  0.00           S+0
CONECT    1    3   13                                                       
CONECT    2    4   14                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    6    8                                                  
CONECT    5    3    9   10                                                  
CONECT    6    4   11   12                                                  
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    1   14                                                       
CONECT   14    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
3,3'-Dithiobis(2-aminopropanoic acid)	ChEBI
alpha-Diamino-beta-dithiolactic acid	ChEBI
Cistina	ChEBI
Cystin	ChEBI
Dicysteine	ChEBI
Zystin	ChEBI
3,3'-Dithiobis(2-aminopropanoate)	Generator
a-Diamino-b-dithiolactate	Generator
a-Diamino-b-dithiolactic acid	Generator
alpha-Diamino-beta-dithiolactate	Generator
Α-diamino-β-dithiolactate	Generator
Α-diamino-β-dithiolactic acid	Generator
Copper cystinate	MeSH
Cystine	MeSH
L-Cystine	MeSH
L Cystine	MeSH

Chemical Formula

C₆H₁₂N₂O₄S₂

Average Mass

240.3000 Da

Monoisotopic Mass

240.02385 Da

IUPAC Name

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

Traditional Name

cystine

CAS Registry Number

Not Available

SMILES

NC(CSSCC(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)

InChI Key

LEVWYRKDKASIDU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2023-04-28	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antirrhinum majus	LOTUS Database	35616633
Claviceps purpurea	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Organic disulfide
Dialkyldisulfide
Amino acid
Sulfenyl compound
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic disulfide (CHEBI:17376 )
sulfur-containing amino acid (CHEBI:17376 )
cysteine derivative (CHEBI:17376 )
Other amino acids (C01420 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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	22.78 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012672

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01420

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cystine

METLIN ID

Not Available

PubChem Compound

595

PDB ID

Not Available

ChEBI ID

17376

Good Scents ID

Not Available

References

General References

Liu S, Yang F, Li J, Zhang C, Ji H, Hong P: Physical and chemical analysis of Passiflora seeds and seed oil from China. Int J Food Sci Nutr. 2008 Nov-Dec;59(7-8):706-15. doi: 10.1080/09637480801931128. [PubMed:18608550 ]
Masotti A, Laurenzi C, Boenzi S, Pastore A, Taranta A, Bellomo F, Muraca M, Dionisi-Vici C, Bertucci P, Dello Strologo L, Emma F: Gender-related effects on urine L-cystine metastability. Amino Acids. 2014 Feb;46(2):415-27. doi: 10.1007/s00726-013-1631-9. Epub 2013 Dec 11. [PubMed:24327171 ]
Prencipe G, Caiello I, Cherqui S, Whisenant T, Petrini S, Emma F, De Benedetti F: Inflammasome activation by cystine crystals: implications for the pathogenesis of cystinosis. J Am Soc Nephrol. 2014 Jun;25(6):1163-9. doi: 10.1681/ASN.2013060653. Epub 2014 Feb 13. [PubMed:24525029 ]
Gaide Chevronnay HP, Janssens V, Van Der Smissen P, N'Kuli F, Nevo N, Guiot Y, Levtchenko E, Marbaix E, Pierreux CE, Cherqui S, Antignac C, Courtoy PJ: Time course of pathogenic and adaptation mechanisms in cystinotic mouse kidneys. J Am Soc Nephrol. 2014 Jun;25(6):1256-69. doi: 10.1681/ASN.2013060598. Epub 2014 Feb 13. [PubMed:24525030 ]
Shen L, Sun X, Zhu H, Cong X, Ning B: Comparison of renal function and metabolic abnormalities of cystine stone patients and calcium oxalate stone patients in China. World J Urol. 2013 Oct;31(5):1219-23. doi: 10.1007/s00345-012-0886-1. Epub 2012 May 24. [PubMed:22622395 ]
LOTUS database [Link]

Showing NP-Card for cystine (NP0266538)

MOL for NP0266538 (cystine)

3D MOL for NP0266538 (cystine)

3D SDF for NP0266538 (cystine)

3D-SDF for NP0266538 (cystine)

PDB for NP0266538 (cystine)

3D PDB for NP0266538 (cystine)

SMILES for NP0266538 (cystine)

INCHI for NP0266538 (cystine)

Structure for NP0266538 (cystine)

3D Structure for NP0266538 (cystine)