Record Information
Version1.0
Created at2020-04-17 19:13:40 UTC
Updated at2020-12-07 19:11:40 UTC
CannabisDB IDCDB005143
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Cystathionine
DescriptionL-Cystathionine belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. L-Cystathionine is a very strong basic compound (based on its pKa). L-Cystathionine exists in all living species, ranging from bacteria to humans. Within humans, L-cystathionine participates in a number of enzymatic reactions. In particular, L-cystathionine can be converted into L-cysteine and 2-ketobutyric acid; which is mediated by the enzyme cystathionine gamma-lyase. In addition, L-cystathionine can be biosynthesized from L-homoserine and L-serine through its interaction with the enzyme cystathionine beta-synthase. In humans, L-cystathionine is involved in methionine metabolism. L-Cystathionine is a potentially toxic compound. L-Cystathionine, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, alzheimer's disease, and autism; L-cystathionine has also been linked to several inborn metabolic disorders including hypermethioninemia and folate deficiency. A modified amino acid generated by enzymic means from L-homocysteine and L-serine. L-Cystathionine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteineChEBI
L-(+)-CystathionineChEBI
S-(beta-Amino-beta-carboxyethyl)homocysteineChEBI
S-(b-Amino-b-carboxyethyl)homocysteineGenerator
S-(Β-amino-β-carboxyethyl)homocysteineGenerator
CystathionineHMDB
S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteineHMDB
[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoateHMDB
[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoic acidHMDB
Chemical FormulaC7H14N2O4S
Average Molecular Weight222.26
Monoisotopic Molecular Weight222.0674
IUPAC Name(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
Traditional NameL-cystathionine
CAS Registry Number56-88-2
SMILES
N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
InChI KeyILRYLPWNYFXEMH-WHFBIAKZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Dialkylthioether
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point312 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4ALOGPS
logP-5.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.57 m³·mol⁻¹ChemAxon
Polarizability22.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Cystathionine, 4 TMS, GC-MS Spectrumsplash10-00fr-8950000000-640b4294e37e5a01048dSpectrum
GC-MSL-Cystathionine, 2 TMS, GC-MS Spectrumsplash10-0f7c-7910000000-91f9f2b2dd44a3cdb276Spectrum
GC-MSL-Cystathionine, 3 TMS, GC-MS Spectrumsplash10-00or-1940000000-c0d688e4ea87ff3e03faSpectrum
GC-MSL-Cystathionine, 4 TMS, GC-MS Spectrumsplash10-00or-0980000000-7d816de782a902900d0eSpectrum
GC-MSL-Cystathionine, non-derivatized, GC-MS Spectrumsplash10-00fr-8950000000-640b4294e37e5a01048dSpectrum
GC-MSL-Cystathionine, non-derivatized, GC-MS Spectrumsplash10-0f7c-7910000000-91f9f2b2dd44a3cdb276Spectrum
GC-MSL-Cystathionine, non-derivatized, GC-MS Spectrumsplash10-00or-1940000000-c0d688e4ea87ff3e03faSpectrum
GC-MSL-Cystathionine, non-derivatized, GC-MS Spectrumsplash10-00or-0980000000-7d816de782a902900d0eSpectrum
Predicted GC-MSL-Cystathionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9410000000-9487e9168e86a2297931Spectrum
Predicted GC-MSL-Cystathionine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dm-9665000000-608a6335880ad1c2519dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-1980000000-99cb7d1da067e5436b09Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e72725Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e72725Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00fr-0690000000-0b572de3fcbc7e2f13ccSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000t-0900000000-5788192b32aadd177e33Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000b-4900000000-b86ac7de446a762365bdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000j-9800000000-75ff1bc6e325692a9da9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kr-9100000000-6517562dc0f31a85afc8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-0900000000-d1628d0a880f1b6e6d90Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-9000000000-9a2e1e54b77216e2df72Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0090000000-36678c2f0bf1b01cc9d4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-05fr-0190000000-e575f57f0d76ef6afa49Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00e9-0940000000-962ae510f06296b98878Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00e9-0940000000-27da1912eac54f485bfaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00fr-0690000000-82fe2198c98660008c04Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-0900000000-58cceb69cceeff79606cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-4900000000-5877787c54120dc165c9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000j-9800000000-fd29b0fcf62b73831829Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9100000000-6517562dc0f31a85afc8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-1930000000-887e3ad7da04e4f1aac9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01uc-6900000000-563444ac8ab717997268Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-9700000000-35397d8e2ab2c6582c52Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0970000000-d0f0a96ca41d1f751c26Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3910000000-22200c974305822456d8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9300000000-0dfaab5efe3438889c3cSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Cystathionine gamma-lyaseCTH1p31.1P32929 details
Cystathionine beta-synthaseCBS21q22.3P35520 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cystathionine beta-synthaseCBS21q22.3P35520 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Cystathionine gamma-lyaseCTH1p31.1P32929 details
Concentrations Data
Not Available
HMDB IDHMDB0000099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001976
KNApSAcK IDC00007498
Chemspider ID388392
KEGG Compound IDC02291
BioCyc IDL-CYSTATHIONINE
BiGG ID39523
Wikipedia LinkCystathionine
METLIN ID39
PubChem Compound439258
PDB IDNot Available
ChEBI ID17482
References
General ReferencesNot Available

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:
CTH
Uniprot ID:
P32929
Molecular weight:
41259.91
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
Gene Name:
CBS
Uniprot ID:
P35520
Molecular weight:
60586.05