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Bovine Metabolome Database



Showing metabocard for L-Cystathionine (BMDB00099)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-02 15:51:15
Accession Number BMDB00099
Common Name L-Cystathionine
Description Cystathionine is a dipeptide formed by serine and homocysteine. Cystathioninuria is a prominent manifestation of vitamin-B6 deficiency. The transsulfuration of methionine yields homocysteine, which combines with serine to form cystathionine, the proximate precursor of cysteine through the enzymatic activity of cystathionase. In conditions in which cystathionine gamma-synthase or cystathionase is deficient, for example, there is cystathioninuria. Although cystathionine has not been detected in normal human serum or plasma by most conventional methods, gas chromatographic/mass spectrometric methodology detected a mean concentration of cystathionine in normal human serum of 140 nM, with a range of 65 to 301 nM.567 Cystathionine concentrations in CSF have been 10, 1, and 0.5 uM, and "not detected." Only traces (i.e., <1 uM) of cystathionine are present in normal CSF.587. gamma-Cystathionase deficiency provided the first instance in which, in a human, the major biochemical abnormality due to a defined enzyme defect was clearly shown to be alleviated by administration of large doses of pyridoxine. The response in gamma-cystathionase-deficient patients is not attributable to correction of a preexisting deficiency of this vitamin. (OMMBID, Chap. 88)
Synonyms
  1. L-(+)-Cystathionine
  2. Cystathionine
  3. (R)-S-(2-amino-2-carboxyethyl)-L-Homocysteine
  4. [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoic acid
  5. S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteine
  6. [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoate
Chemical IUPAC Name (2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid
Chemical Formula C7H14N2O4S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • thioether; primary amine; primary aliphatic amine (alkylamine); carboxylic acid; alpha-aminoacid
Biofunction
  • Component of Cysteine metabolism; Component of Glycine, serine and threonine metabolism; Component of Methionine metabolism; Component of Nitrogen metabolism; Component of Selenoamino acid metabolism
Application
Source
  • Endogenous
Average Molecular Weight 222.262
Monoisotopic Molecular Weight 222.067429
Isomeric SMILES N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O
Canonical SMILES NC(CCSCC(N)C(O)=O)C(O)=O
KEGG Compound ID C02291 Link Image
BioCyc ID L-CYSTATHIONINE Link Image
BiGG ID 39523 Link Image
Wikipedia Link Cystathionine Link Image
METLIN ID 39 Link Image
PubChem Compound 439258 Link Image
PubChem Substance 24849836 Link Image
ChEBI ID 17482 Link Image
CAS Registry Number 56-88-2
InChI Identifier InChI=1/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
Synthesis Reference Yamagata, Shuzo; Akamatsu, Tsuyoshi; Iwama, Tomonori. Immobilization of Saccharomyces cerevisiae cystathionine gamma-lyase and application of the product to cystathionine synthesis. Applied and Environmental Microbiology (2004), 70(6), 3766-3768.
Melting Point (Experimental) 312 oC
Experimental Water Solubility 22 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 17.3 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -4.01 [Predicted by ALOGPS]; -5.4 [Predicted by PubChem via XLOGP]; -4.80 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location Not Available
Tissue Location
Tissue References
Brain
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Glycine, Serine and Threonine Metabolism
  • Methionine Metabolism
HMDB Pathways
Name Glycine, Serine and Threonine Metabolism
Image Show Link Image
Name Methionine Metabolism
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KEGG Pathways
Name Glycine, Serine and Threonine Metabolism
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Name Methionine Metabolism
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SimCell Pathways
Name Glycine, Serine and Threonine Metabolism
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SBML Download (XML) Link Image
Name Methionine Metabolism
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General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Cystathionine gamma-lyase
Enzyme 1 [top]
Enzyme 1 ID 818
Enzyme 1 Name Cystathionine gamma-lyase
Enzyme 1 Synonyms
  1. Gamma-cystathionase
Enzyme 1 Gene Name CTH
Enzyme 1 Protein Sequence >Cystathionine gamma-lyase
MQEKEASPHGFLPRFQHFATQAIHVGQEPEQWTSQAVVPPISLSTTFKQGAPGQHSGFEY
SRSGNPTRNCLEKAVAALDGAKYSLAFASGLAATVTITHLLKAGDQIICMDDVYGGTNRY
FRQVATEFGLKISFVDCSKPKLLEAAITPETKLVWIETPTNPSLKMIDIEACAHTVHKHG
DIILVVDNTFMSAYFQRPLSLGADICMYSATKYMNGYSDVVMGLVSLNSESLHDRLRFLQ
NSLGAVPSPIDCYLCNRGLKTLQVRMEKHFENGMAVAQFLESNPQVEKVIYPGLPSHPQH
ELAKRQCTGCPGMVTFYIKGSLQHAETFLQNLKLFTLAESLGGYESLAELPAIMTHASVP
KSDREVLGISDTLIRLSVGLEDKQDLLDDLDQALKAANPPNASSN
Enzyme 1 Number of Residues 405
Enzyme 1 Molecular Weight 44405.3
Enzyme 1 Theoretical pI 6.39
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Enzyme 1 Pathways
  • Amino-acid biosynthesis
  • L-cysteine biosynthesis
  • L- cysteine from L-homocysteine and L-serine:step 2/2
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 61552994 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q58DW2 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CGL_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1218 bp
ATGCAGGAAAAAGAAGCCTCCCCACACGGATTCCTGCCTAGGTTCCAGCATTTCGCTACG
CAGGCCATCCACGTGGGCCAAGAACCGGAGCAATGGACCTCCCAAGCTGTAGTGCCCCCT
ATCTCGCTGTCCACCACGTTCAAGCAAGGGGCTCCTGGCCAGCACTCGGGTTTTGAGTAT
AGCCGTTCTGGAAATCCCACCCGGAATTGCTTGGAAAAAGCAGTGGCGGCGCTGGATGGG
GCTAAGTACAGTTTGGCCTTTGCTTCAGGTTTAGCAGCCACTGTGACCATTACCCATCTC
TTAAAAGCAGGAGACCAGATTATTTGTATGGATGATGTGTATGGAGGTACAAACAGGTAC
TTCAGGCAGGTGGCAACTGAATTTGGATTAAAGATTTCTTTTGTTGATTGTTCCAAACCC
AAATTGCTAGAGGCAGCTATTACACCAGAAACCAAGCTTGTTTGGATTGAAACCCCCACA
AACCCTAGCTTGAAGATGATTGACATTGAAGCCTGCGCACATACGGTCCATAAACATGGA
GACATCATTTTGGTTGTGGATAACACTTTTATGTCAGCATATTTCCAGCGGCCTTTGTCT
CTGGGAGCTGATATTTGTATGTATTCAGCAACAAAATACATGAATGGCTACAGTGATGTT
GTAATGGGCTTAGTGTCACTGAATTCTGAGAGCCTTCATGATAGGCTCCGTTTCTTGCAA
AATTCTCTTGGAGCAGTTCCATCTCCTATTGACTGTTACCTCTGCAATCGGGGTCTGAAG
ACTCTACAAGTCCGCATGGAGAAGCATTTCGAAAACGGAATGGCAGTTGCTCAGTTTTTG
GAGTCGAATCCTCAGGTGGAAAAGGTTATTTATCCTGGGCTGCCTTCTCATCCTCAGCAT
GAGCTGGCCAAGCGTCAGTGCACAGGTTGCCCGGGGATGGTCACCTTTTATATCAAGGGC
TCTCTTCAACATGCTGAAACTTTCCTCCAGAACTTAAAGTTATTTACTCTGGCTGAAAGC
TTGGGAGGATACGAAAGTCTTGCTGAGCTTCCGGCAATCATGACCCATGCATCAGTGCCT
AAGAGTGACAGAGAAGTCCTTGGAATTAGTGACACACTTATTCGACTCTCAGTGGGCTTA
GAGGATAAACAAGACCTACTGGATGATCTAGATCAAGCTTTGAAGGCAGCTAACCCTCCA
AATGCAAGTTCCAACTAG
Enzyme 1 GenBank Gene ID BT021485 Link Image
Enzyme 1 GeneCard ID CTH Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 1p31.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available