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L-Homocystine

PubChem CID
439579
Structure
L-Homocystine_small.png
L-Homocystine_3D_Structure.png
Molecular Formula
Synonyms
  • L-Homocystine
  • 626-72-2
  • Homocystine, L-
  • (H-HoCys-OH)2
  • (2S,2'S)-4,4'-Disulfanediylbis(2-aminobutanoic acid)
Molecular Weight
268.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-11
Description
L,L-homocystine is a homocystine in which both chiral centres have L configuration. It is functionally related to a L-homocysteine. It is a tautomer of a L,L-homocystine zwitterion.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
L-Homocystine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-Hcy(1)-OH.H-Hcy(1)-OH
HELM
PEPTIDE1{[Hcy]}|PEPTIDE2{[Hcy]}$PEPTIDE1,PEPTIDE2,1:R3-1:R3$$$
IUPAC
L-homocysteine (1->1')-disulfide compound with L-homocysteine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S)-2-amino-4-[[(3S)-3-amino-3-carboxypropyl]disulfanyl]butanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

ZTVZLYBCZNMWCF-WDSKDSINSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C(CSSCC[C@@H](C(=O)O)N)[C@@H](C(=O)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C8H16N2O4S2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 DSSTox Substance ID

3.3.6 KEGG ID

3.3.7 Metabolomics Workbench ID

3.3.8 Nikkaji Number

3.3.9 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
268.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-5.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
268.05514934 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
268.05514934 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
177 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
216
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Dissociation Constants

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 2
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Retention Time
571.564 sec
Top 5 Peaks

73 100

128 87.49

160 29.13

278 21.32

129 12.01

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License
CC BY-SA
2 of 2
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Retention Time
606.301 sec
Top 5 Peaks

73 100

128 73.37

160 22.82

278 16.62

100 10.81

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License
CC BY-SA

5.2.2 MS-MS

NIST Number
1053636
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
269.0624
Total Peaks
20
m/z Top Peak
136.1
m/z 2nd Highest
118.1
m/z 3rd Highest
269.4
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5.2.3 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
269.06295
Instrument
UPLC Q-Tof Premier, Waters
Instrument Type
LC-ESI-QTOF
Ionization
ESI
Ionization Mode
positive
Collision Energy
Ramp 5-60 V
Top 5 Peaks

88.0241 87.71

136.0471 68.88

134.0311 52.82

90.0398 48.55

98.9878 13.74

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License
CC BY-SA
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
269.062438964844
Instrument
Agilent 6550 iFunnel
Instrument Type
LC-ESI-QTOF
Ionization
ESI
Ionization Mode
positive
Collision Energy
40
Retention Time
10.58
Top 5 Peaks

88.02295 100

56.05053 22.68

90.03699 19.58

44.04995 6.69

73.01087 3.29

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License
CC-BY

5.2.4 Other MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
269.25
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
10
Top 5 Peaks

269 100

136 70.60

135 6.14

268 3.18

Thumbnail
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2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
269.25
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
20
Top 5 Peaks

136 100

134 43.31

133 12.29

90 10.98

132 3.11

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5.3 IR Spectra

5.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
General Biochemicals, Chagrin Falls, Ohio
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Butanoic acid, 4,4'-dithiobis[2-amino-, (2S,2'S)-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports. Pictograms displayed are for < 0.1% (0 of 3) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 3 of 3 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 3 of 3 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 3 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Not Classified

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Nature Journal References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Classification

12.1 ChEBI Ontology

12.2 ChemIDplus

12.3 UN GHS Classification

12.4 EPA DSSTox Classification

12.5 EPA TSCA and CDR Classification

12.6 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    Butanoic acid, 4,4'-dithiobis[2-amino-, (2S,2'S)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    [S-(R*,R*)]-4,4'-dithiobis[2-aminobutyric] acid (EC: 210-962-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/85105
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEBI
  8. IUPAC Digitized pKa Dataset
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  11. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  12. Metabolomics Workbench
  13. Nature Chemical Biology
  14. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  15. SpectraBase
    L-4,4'-dithiobis[2-aminobutyric acid]
    https://spectrabase.com/spectrum/6mq7KedIqxR
    L-4,4'-DITHIOBIS[2-AMINOBUTRYIC ACID]
    https://spectrabase.com/spectrum/L72fLlgcpHi
  16. Springer Nature
  17. Wikidata
  18. PubChem
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
  22. NCBI
CONTENTS