| Common Name |
Cysteinyl-Histidine
| Description |
Cysteinyl-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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB28777 (Cysteinyl-Histidine)
| Synonyms |
| Value |
Source |
C-H DipeptideHMDB
CH DipeptideHMDB
Cys-hisHMDB
Cysteine histidine dipeptideHMDB
Cysteine-histidine dipeptideHMDB
CysteinylhistidineHMDB
L-Cysteinyl-L-histidineHMDB
| Chemical Formlia |
C9H14N4O3S
| Average Molecliar Weight |
258.297
| Monoisotopic Molecliar Weight |
258.078661024
| IUPAC Name |
2-(2-amino-3-slifanylpropanamido)-3-(1H-imidazol-5-yl)propanoic acid
| Traditional Name |
2-(2-amino-3-slifanylpropanamido)-3-(3H-imidazol-4-yl)propanoic acid
| CAS Registry Number |
Not 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 Key |
LVNMAAGSAUGNIC-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
Dipeptides
| Alternative Parents |
Histidine and derivatives
N-acyl-alpha amino acids
Alpha amino acid amides
Cysteine and derivatives
Imidazolyl carboxylic acids and derivatives
Heteroaromatic compounds
Secondary carboxylic acid amides
Amino acids
Alkylthiols
Azacyclic compounds
Carboxylic acids
Monocarboxylic acids and derivatives
Carbonyl compounds
Organic oxides
Organopnictogen compounds
Monoalkylamines
Hydrocarbon derivatives
| 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
Organoslifur compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.87Extrapolated
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.58 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.08 m3·mol-1ChemAxon
Polarizability25.26 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB28777
| Metagene Link |
HMDB28777
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Kinetin riboside
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
PMID: 1981582