You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:12 UTC
HMDB IDHMDB0000455
Secondary Accession Numbers
  • HMDB00455
Metabolite Identification
Common NameAllocystathionine
DescriptionAllocystathionine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from the reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Allocystathionine is a very strong basic compound (based on its pKa). Allocystathionine is a product of enzyme cystathionine synthetase (EC 2.5.1.48) which converts homocysteine into allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase (EC 4.4.1.8) in the same pathway (KEGG).
Structure
Data?1582752132
Synonyms
ValueSource
a-amino-g-(2-amino-2-carboxyethylmercapto)-Butyric acidHMDB
alpha-amino-gamma-(2-amino-2-carboxyethylmercapto)-Butyric acidHMDB
DL-AllocystathionineHMDB
DL-S-(2-amino-2-Carboxyethyl)-homocysteineHMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoateGenerator, HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoateGenerator, HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acidGenerator, HMDB
Chemical FormulaC7H14N2O4S
Average Molecular Weight222.262
Monoisotopic Molecular Weight222.067427636
IUPAC Name(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid
Traditional Name(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid
CAS Registry Number535-34-2
SMILES
N[C@@H](CCSCC(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-ROLXFIACSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point281 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.3 g/LALOGPS
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
Polarizability22.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9610000000-97cdce91b05acb8cc8bbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006w-9820000000-a4fe2f55cc7a64d712d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-1970000000-390b1ab3f56f1cb7ffbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-0e801a644a1583a9778dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-994bee45a32e4a973f75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0940000000-9fdb16343f3b22e1d5a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01uc-6900000000-b14f24442e88e83f7af9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9700000000-922e1a8102eabf0436d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0690000000-486a90f6a8c86b76bd97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00si-1920000000-726d3f50f04c46f54d30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9300000000-6ad28f56d312c1757691Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022055
KNApSAcK IDNot Available
Chemspider ID8280480
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10104953
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceMary L. Snow, Roy S. Dombro, and Charlotte Ressler. Synthesis of L-cystathionine and D-allocystathionine. J. Org. Chem., 1967, 32 (1), pp 246–248
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Makar TK, Nedergaard M, Preuss A, Hertz L, Cooper AJ: Glutamine transaminase K and omega-amidase activities in primary cultures of astrocytes and neurons and in embryonic chick forebrain: marked induction of brain glutamine transaminase K at time of hatching. J Neurochem. 1994 May;62(5):1983-8. [PubMed:8158144 ]
  2. Grieco AJ: Homocystinuria: pathogenetic mechanisms. Am J Med Sci. 1977 Mar-Apr;273(2):120-32. [PubMed:324277 ]

Enzymes

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