Showing Compound Card for L-Cystathionine (CDB005143)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
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
MOLSDFPDBSMILESInChI
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
Predicted GC-MSL-Cystathionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Cystathionine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-1980000000-99cb7d1da067e5436b092012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e727252012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e727252012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00fr-0690000000-0b572de3fcbc7e2f13cc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000t-0900000000-5788192b32aadd177e332012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000b-4900000000-b86ac7de446a762365bd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000j-9800000000-75ff1bc6e325692a9da92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kr-9100000000-6517562dc0f31a85afc82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-0900000000-d1628d0a880f1b6e6d902012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-9000000000-9a2e1e54b77216e2df722012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0090000000-36678c2f0bf1b01cc9d42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-05fr-0190000000-e575f57f0d76ef6afa492012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00e9-0940000000-962ae510f06296b988782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00e9-0940000000-27da1912eac54f485bfa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00fr-0690000000-82fe2198c98660008c042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-0900000000-58cceb69cceeff79606c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-4900000000-5877787c54120dc165c92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000j-9800000000-fd29b0fcf62b738318292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9100000000-6517562dc0f31a85afc82017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-1930000000-887e3ad7da04e4f1aac92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01uc-6900000000-563444ac8ab7179972682016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-9700000000-35397d8e2ab2c6582c522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0970000000-d0f0a96ca41d1f751c262016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3910000000-22200c974305822456d82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9300000000-0dfaab5efe3438889c3c2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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

Enzyme Details
1. Cystathionine gamma-lyase
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
Enzyme Details
2. Cystathionine beta-synthase
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