<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4381</id>
  <title>T3D4327</title>
  <common-name>L-Homocystine</common-name>
  <description>Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfide account for &gt;98% of total homocysteine in plasma from healthy individuals.  Oxidation of low-density lipoprotein (LDL) is thought to be a major factor in the pathophysiology of atherosclerosis. Elevated plasma homocysteine is an accepted risk factor for atherosclerosis, and may act through LDL oxidation, although this is controversial. However, the major thiol in plasma is cysteine, which is present at concentrations approximately 10 times greater than homocysteine; therefore homocystine in plasma is insignificant, and consequently homocystine is unlikely to influence LDL oxidation in vivo.  Increasing evidence supports a role for an elevation of homocysteine in schizophrenia. It has been demonstrated that neural tube defects are related to a genetic defect in homocysteine metabolism. Sufficient intake of folic acid is believed to reduce this risk by enhancing methylation of homocysteine and its conversion to methionine, thereby compensating for this genetic defect. Plasma homocysteine levels are elevated when folate levels are in the lower half of the normal range.  (A3414, A3415, A3416).</description>
  <cas>626-72-2</cas>
  <pubchem-id>69382</pubchem-id>
  <chemical-formula>C8H16N2O4S2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>300°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>0.2 mg/mL at 25°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:27:34Z</created-at>
  <updated-at type="dateTime">2026-04-02T23:59:27Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C01817</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>17485</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NC(CCSSCC[C@H](N)C(O)=O)C(O)=O</moldb-smiles>
  <moldb-formula>C8H16N2O4S2</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>ZTVZLYBCZNMWCF-ZBHICJROSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">268.354</moldb-average-mass>
  <moldb-mono-mass type="decimal">268.05514839</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00676</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>62590</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003287</chemdb-id>
  <dsstox-id>DTXSID001019905</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00014871</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>126.64</moldb-polar-surface-area>
  <moldb-refractivity>64.38180000000001</moldb-refractivity>
  <moldb-polarizability>26.91822397662728</moldb-polarizability>
  <moldb-rotatable-bond-count>9</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.8009555846997536</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.80244167200791</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-4.15</moldb-alogps-logp>
  <moldb-alogps-logs>-1.78</moldb-alogps-logs>
  <moldb-alogps-solubility>4.50e+00 g/l</moldb-alogps-solubility>
</compound>
