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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:41:40 UTC
HMDB IDHMDB0000575
Secondary Accession Numbers
  • HMDB00575
Metabolite Identification
Common NameDL-Homocystine
DescriptionHomocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98% of total homocysteine in plasma from healthy individuals (PMID 11592966 ). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706 ). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596 )
Structure
Data?1582752141
Synonyms
ValueSource
4,4'-Dithiobis(2-aminobutyric acid)ChEBI
HomocystineKegg
4,4'-Dithiobis(2-aminobutyrate)Generator
4,4'-DithiobisHMDB
Chemical FormulaC8H16N2O4S2
Average Molecular Weight268.354
Monoisotopic Molecular Weight268.05514839
IUPAC Name2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid
Traditional Namehomocystine
CAS Registry Number870-93-9
SMILES
NC(CCSSCCC(N)C(O)=O)C(O)=O
InChI Identifier
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)
InChI KeyZTVZLYBCZNMWCF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Organic disulfide
  • Amino acid
  • Dialkyldisulfide
  • Sulfenyl compound
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point263 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos157.88830932474
[M+H]+Not Available158.493http://allccs.zhulab.cn/database/detail?ID=AllCCS00000020
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.5 g/LALOGPS
logP10(-4.2) g/LALOGPS
logP10(-5.3) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.38 m³·mol⁻¹ChemAxon
Polarizability26.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.52731661259
DarkChem[M-H]-153.96331661259
AllCCS[M+H]+155.24832859911
AllCCS[M-H]-155.50132859911
DeepCCS[M+H]+151.44830932474
DeepCCS[M-H]-147.42630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DL-HomocystineNC(CCSSCCC(N)C(O)=O)C(O)=O3629.9Standard polar33892256
DL-HomocystineNC(CCSSCCC(N)C(O)=O)C(O)=O2148.6Standard non polar33892256
DL-HomocystineNC(CCSSCCC(N)C(O)=O)C(O)=O2724.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DL-Homocystine,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O2464.0Semi standard non polar33892256
DL-Homocystine,1TMS,isomer #2C[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O2553.4Semi standard non polar33892256
DL-Homocystine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O[Si](C)(C)C2439.8Semi standard non polar33892256
DL-Homocystine,2TMS,isomer #2C[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C2484.3Semi standard non polar33892256
DL-Homocystine,2TMS,isomer #3C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O2488.2Semi standard non polar33892256
DL-Homocystine,2TMS,isomer #4C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O)C(=O)O2568.9Semi standard non polar33892256
DL-Homocystine,2TMS,isomer #5C[Si](C)(C)N(C(CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C2665.8Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2490.8Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2544.9Standard non polar33892256
DL-Homocystine,3TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C3748.7Standard polar33892256
DL-Homocystine,3TMS,isomer #2C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2540.9Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #2C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2541.0Standard non polar33892256
DL-Homocystine,3TMS,isomer #2C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O3454.5Standard polar33892256
DL-Homocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2638.2Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2590.6Standard non polar33892256
DL-Homocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C4022.5Standard polar33892256
DL-Homocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2630.2Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2611.1Standard non polar33892256
DL-Homocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3873.9Standard polar33892256
DL-Homocystine,3TMS,isomer #5C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2702.7Semi standard non polar33892256
DL-Homocystine,3TMS,isomer #5C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2595.0Standard non polar33892256
DL-Homocystine,3TMS,isomer #5C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O3613.7Standard polar33892256
DL-Homocystine,4TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2522.8Semi standard non polar33892256
DL-Homocystine,4TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2614.1Standard non polar33892256
DL-Homocystine,4TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2979.9Standard polar33892256
DL-Homocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2613.3Semi standard non polar33892256
DL-Homocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2675.1Standard non polar33892256
DL-Homocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3586.8Standard polar33892256
DL-Homocystine,4TMS,isomer #3C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2655.4Semi standard non polar33892256
DL-Homocystine,4TMS,isomer #3C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2682.4Standard non polar33892256
DL-Homocystine,4TMS,isomer #3C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C3182.3Standard polar33892256
DL-Homocystine,4TMS,isomer #4C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2667.7Semi standard non polar33892256
DL-Homocystine,4TMS,isomer #4C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2660.3Standard non polar33892256
DL-Homocystine,4TMS,isomer #4C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O3223.0Standard polar33892256
DL-Homocystine,4TMS,isomer #5C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2815.9Semi standard non polar33892256
DL-Homocystine,4TMS,isomer #5C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2749.3Standard non polar33892256
DL-Homocystine,4TMS,isomer #5C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C3351.5Standard polar33892256
DL-Homocystine,5TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2626.3Semi standard non polar33892256
DL-Homocystine,5TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2723.2Standard non polar33892256
DL-Homocystine,5TMS,isomer #1C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2838.3Standard polar33892256
DL-Homocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2820.8Semi standard non polar33892256
DL-Homocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2794.6Standard non polar33892256
DL-Homocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3027.4Standard polar33892256
DL-Homocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2802.3Semi standard non polar33892256
DL-Homocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2823.6Standard non polar33892256
DL-Homocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2755.3Standard polar33892256
DL-Homocystine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O2726.8Semi standard non polar33892256
DL-Homocystine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O2782.6Semi standard non polar33892256
DL-Homocystine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C2943.6Semi standard non polar33892256
DL-Homocystine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2991.2Semi standard non polar33892256
DL-Homocystine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2991.8Semi standard non polar33892256
DL-Homocystine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O3053.2Semi standard non polar33892256
DL-Homocystine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C3091.9Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3163.1Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3139.0Standard non polar33892256
DL-Homocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3734.0Standard polar33892256
DL-Homocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O3235.9Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O3120.0Standard non polar33892256
DL-Homocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O3503.5Standard polar33892256
DL-Homocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3315.9Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3162.3Standard non polar33892256
DL-Homocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3907.9Standard polar33892256
DL-Homocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3293.1Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3155.0Standard non polar33892256
DL-Homocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3801.6Standard polar33892256
DL-Homocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3362.6Semi standard non polar33892256
DL-Homocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3135.9Standard non polar33892256
DL-Homocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3619.8Standard polar33892256
DL-Homocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3374.0Semi standard non polar33892256
DL-Homocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3317.7Standard non polar33892256
DL-Homocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3305.7Standard polar33892256
DL-Homocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3482.0Semi standard non polar33892256
DL-Homocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3367.0Standard non polar33892256
DL-Homocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3641.2Standard polar33892256
DL-Homocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3550.0Semi standard non polar33892256
DL-Homocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3341.3Standard non polar33892256
DL-Homocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3403.3Standard polar33892256
DL-Homocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3568.0Semi standard non polar33892256
DL-Homocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3347.7Standard non polar33892256
DL-Homocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3432.0Standard polar33892256
DL-Homocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C3668.4Semi standard non polar33892256
DL-Homocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C3369.6Standard non polar33892256
DL-Homocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C3509.0Standard polar33892256
DL-Homocystine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3700.7Semi standard non polar33892256
DL-Homocystine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3524.3Standard non polar33892256
DL-Homocystine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3267.8Standard polar33892256
DL-Homocystine,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3878.9Semi standard non polar33892256
DL-Homocystine,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3560.3Standard non polar33892256
DL-Homocystine,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3333.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - DL-Homocystine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0920000000-4772adba6d14b0bf412b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - DL-Homocystine GC-EI-TOF (Non-derivatized)splash10-004i-0920000000-4772adba6d14b0bf412b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdo-9610000000-e10491cf3224336e3f4a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9322000000-c71d91c4e21c8dc7e38b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0900000000-5c60c8ff83dddb24602e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9200000000-2895a3e74d847e15c6a12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-0a6bc3cbbfaf644160a32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0190000000-60f50f1524147fa8c11c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-001i-2920000000-bd3949a66bce9cbb215f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-06e9-9720000000-7031c8ff553e104dc6642012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-00di-9210000000-eff737edd376642567452012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00di-9000000000-560f6dc8247244af6cb42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOFsplash10-014i-0190000000-dc9f97c5c65a44240b152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOFsplash10-001i-2920000000-92fb65949be59e1820832017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOFsplash10-06e9-9720000000-7031c8ff553e104dc6642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOFsplash10-00di-9210000000-903e4d0b7abc5500ebf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-560f6dc8247244af6cb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine , negative-QTOFsplash10-01x0-6900000000-d82f9d3a2cbf6b1216f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine 40V, Negative-QTOFsplash10-00di-9000000000-10cb1c86c51258f8a0392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine 20V, Negative-QTOFsplash10-0230-8900000000-e4250a1fffcda8a247322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine 10V, Negative-QTOFsplash10-0089-3910000000-c79d6d7ce56ddb31e44c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine 35V, Negative-QTOFsplash10-0230-6900000000-a3358bbf41fc201a103c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-Homocystine 35V, Positive-QTOFsplash10-00m0-3920000000-d3fa502c6b1e61f23b212021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 10V, Positive-QTOFsplash10-0gi0-0290000000-0d5b5e0ed113894b21342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 20V, Positive-QTOFsplash10-0adi-4940000000-fe801a7a155db92879a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 40V, Positive-QTOFsplash10-000i-9600000000-fa16bd387fed9ef4ae352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 10V, Negative-QTOFsplash10-014i-0590000000-079299cfa664ba6bb1b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 20V, Negative-QTOFsplash10-00lr-2920000000-b1d40f0689b3734318122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-Homocystine 40V, Negative-QTOFsplash10-01bi-9600000000-d4d8be33875dbb26d6412017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.8 +/- 2.8 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.21 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.0 (0.0-5.0) uMAdult (>18 years old)BothMethylmalonic acidemia and homocystinuria details
BloodDetected and Quantified28-34 uMAdult (>18 years old)Male
Methylenetetrahydrofolate reductase deficiency
details
BloodDetected and Quantified122.5 (12.00-233.00) uMChildren (1-13 years old)BothHomocystinuria
    • MetaGene: Metabol...
details
UrineDetected and Quantified22.73 (1-44.47) umol/mmol creatinineChildren (1-13 years old)BothHomocystinuria
    • MetaGene: Metabol...
details
Associated Disorders and Diseases
Disease References
Methylmalonic acidemia
  1. Andersson HC, Shapira E: Biochemical and clinical response to hydroxocobalamin versus cyanocobalamin treatment in patients with methylmalonic acidemia and homocystinuria (cblC). J Pediatr. 1998 Jan;132(1):121-4. [PubMed:9470012 ]
Methylmalonic acidemia and homocystinuria
  1. Andersson HC, Shapira E: Biochemical and clinical response to hydroxocobalamin versus cyanocobalamin treatment in patients with methylmalonic acidemia and homocystinuria (cblC). J Pediatr. 1998 Jan;132(1):121-4. [PubMed:9470012 ]
Homocystinuria
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Methylenetetrahydrofolate reductase deficiency
  1. Haworth JC, Dilling LA, Surtees RA, Seargeant LE, Lue-Shing H, Cooper BA, Rosenblatt DS: Symptomatic and asymptomatic methylenetetrahydrofolate reductase deficiency in two adult brothers. Am J Med Genet. 1993 Mar 1;45(5):572-6. [PubMed:8456826 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
  • 251000 (Methylmalonic acidemia)
  • 236200 (Homocystinuria)
  • 236250 (Methylenetetrahydrofolate reductase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022123
KNApSAcK IDNot Available
Chemspider ID9616
KEGG Compound IDC01817
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5557
PubChem Compound10010
PDB IDNot Available
ChEBI ID17485
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLang, K.; Keller, C. Effect of the cyclophorase system on sulfur-containing amino acids. Biochemische Zeitschrift (1955), 327 202-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Wilcken DE, Gupta VJ: Sulphr containing amino acids in chronic renal failure with particular reference to homocystine and cysteine-homocysteine mixed disulphide. Eur J Clin Invest. 1979 Aug;9(4):301-7. [PubMed:118020 ]
  3. Sengupta S, Wehbe C, Majors AK, Ketterer ME, DiBello PM, Jacobsen DW: Relative roles of albumin and ceruloplasmin in the formation of homocystine, homocysteine-cysteine-mixed disulfide, and cystine in circulation. J Biol Chem. 2001 Dec 14;276(50):46896-904. Epub 2001 Oct 9. [PubMed:11592966 ]
  4. Nakano E, Williamson MP, Williams NH, Powers HJ: Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation. Biochim Biophys Acta. 2004 Jan 20;1688(1):33-42. [PubMed:14732479 ]
  5. Brown AS, Susser ES: Homocysteine and schizophrenia: from prenatal to adult life. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Sep;29(7):1175-80. [PubMed:16143442 ]
  6. Heydrick SJ, Weiss N, Thomas SR, Cap AP, Pimentel DR, Loscalzo J, Keaney JF Jr: L-Homocysteine and L-homocystine stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells. Free Radic Biol Med. 2004 Mar 1;36(5):632-40. doi: 10.1016/j.freeradbiomed.2003.12.001. [PubMed:14980706 ]
  7. Wilcken B, Turner B: Homocystinuria. Reduced folate levels during pyridoxine treatment. Arch Dis Child. 1973 Jan;48(1):58-62. doi: 10.1136/adc.48.1.58. [PubMed:4685596 ]