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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:02:26 UTC
Update Date2020-02-26 21:42:19 UTC
HMDB IDHMDB0028777
Secondary Accession Numbers
  • HMDB28777
Metabolite Identification
Common NameCysteinyl-Histidine
DescriptionCysteinyl-Histidine is a dipeptide composed of cysteine and histidine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.
Structure
Data?1582753339
Synonyms
ValueSource
C-H DipeptideHMDB
CH DipeptideHMDB
Cys-hisHMDB
Cysteine histidine dipeptideHMDB
Cysteine-histidine dipeptideHMDB
CysteinylhistidineHMDB
L-Cysteinyl-L-histidineHMDB
2-[(2-Amino-1-hydroxy-3-sulfanylpropylidene)amino]-3-(1H-imidazol-5-yl)propanoateGenerator
2-[(2-Amino-1-hydroxy-3-sulphanylpropylidene)amino]-3-(1H-imidazol-5-yl)propanoateGenerator
2-[(2-Amino-1-hydroxy-3-sulphanylpropylidene)amino]-3-(1H-imidazol-5-yl)propanoic acidGenerator
Chemical FormulaC9H14N4O3S
Average Molecular Weight258.297
Monoisotopic Molecular Weight258.078661024
IUPAC Name2-(2-amino-3-sulfanylpropanamido)-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name2-(2-amino-3-sulfanylpropanamido)-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CS)C(=O)NC(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O3S/c10-6(3-17)8(14)13-7(9(15)16)1-5-2-11-4-12-5/h2,4,6-7,17H,1,3,10H2,(H,11,12)(H,13,14)(H,15,16)
InChI KeyLVNMAAGSAUGNIC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkylthiol
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.87Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP-2.4ALOGPS
logP-3.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)8.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.08 m³·mol⁻¹ChemAxon
Polarizability25.26 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0fbc-9410000000-23a3e784f54ea26aac47Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9210000000-b0358bb9f86f53714a32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056u-3290000000-c3f53a5ff196895a3336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9310000000-9d43813568cbdf9043e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9200000000-6c04f63e3f985b15475cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1190000000-3b123436413e9149ed53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zj0-4960000000-0c04a9a44085f0030536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9500000000-398103c38c2dafeceb79Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18218196
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lockwood TD: The transfer of reductive energy and pace of proteome turnover: a theory of integrated catabolic control. Antioxid Redox Signal. 2005 Jul-Aug;7(7-8):982-98. [PubMed:15998253 ]
  2. Negi S, Itazu M, Imanishi M, Nomura A, Sugiura Y: Creation and characteristics of unnatural CysHis(3)-type zinc finger protein. Biochem Biophys Res Commun. 2004 Dec 10;325(2):421-5. [PubMed:15530409 ]
  3. Hirabayashi K, Hanaoka K, Shimonishi M, Terai T, Komatsu T, Ueno T, Nagano T: Selective two-step labeling of proteins with an off/on fluorescent probe. Chemistry. 2011 Dec 23;17(52):14763-71. doi: 10.1002/chem.201102664. Epub 2011 Nov 22. [PubMed:22106092 ]
  4. Laplaza CE, Holm RH: Stability and nickel binding properties of peptides designed as scaffolds for the stabilization of Ni(II)-Fe(4)S(4) bridged assemblies. J Biol Inorg Chem. 2002 Apr;7(4-5):451-60. Epub 2002 Jan 8. [PubMed:11941503 ]
  5. Lockwood TD: Is dihydrolipoic acid among the reductive activators of parasite CysHis proteases? Exp Parasitol. 2008 Apr;118(4):604-13. Epub 2007 Nov 7. [PubMed:18068706 ]
  6. Lockwood TD: Lysosomal metal, redox and proton cycles influencing the CysHis cathepsin reaction. Metallomics. 2013 Feb;5(2):110-24. doi: 10.1039/c2mt20156a. [PubMed:23302864 ]
  7. Lockwood TD: Responsiveness of parasite Cys His proteases to iron redox. Parasitol Res. 2006 Dec;100(1):175-81. Epub 2006 Jul 6. [PubMed:16823592 ]