| Common Name |
Histidinyl-Glycine
| Description |
Histidinyl-Glycine is a dipeptide composed of histidine and glycine. 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 HMDB28885 (Histidinyl-Glycine)
| Synonyms |
| Value |
Source |
H-g DipeptideHMDB
HG DipeptideHMDB
His-glyHMDB
Histidine glycine dipeptideHMDB
Histidine-glycine dipeptideHMDB
HistidinylglycineHMDB
L-Histidinyl-L-glycineHMDB
HistidylglycineMeSH
| Chemical Formlia |
C8H12N4O3
| Average Molecliar Weight |
212.2059
| Monoisotopic Molecliar Weight |
212.09094027
| IUPAC Name |
2-[2-amino-3-(1H-imidazol-5-yl)propanamido]acetic acid
| Traditional Name |
[2-amino-3-(3H-imidazol-4-yl)propanamido]acetic acid
| CAS Registry Number |
Not Available
| SMILES |
NC(CC1=CN=CN1)C(=O)NCC(O)=O
| InChI Identifier |
InChI=1S/C8H12N4O3/c9-6(1-5-2-10-4-12-5)8(15)11-3-7(13)14/h2,4,6H,1,3,9H2,(H,10,12)(H,11,15)(H,13,14)
| InChI Key |
LYCVKHSJGDMDLM-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
Imidazolyl carboxylic acids and derivatives
Aralkylamines
Fatty amides
Heteroaromatic compounds
Secondary carboxylic acid amides
Amino acids
Monocarboxylic acids and derivatives
Azacyclic compounds
Carboxylic acids
Carbonyl compounds
Organic oxides
Organopnictogen compounds
Monoalkylamines
Hydrocarbon derivatives
| Substituents |
Alpha-dipeptide
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Fatty acyl
Fatty amide
Azole
Imidazole
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organooxygen compound
Organonitrogen 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-4.58Extrapolated
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility8.58 mg/mLALOGPS
logP-2.9ALOGPS
logP-4.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)8.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.86 m3·mol-1ChemAxon
Polarizability20.42 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 |
HMDB28885
| Metagene Link |
HMDB28885
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: 1,3-Dicaffeoylquinic acid
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
- Kapota C, Ohanessian G: The low energy tautomers and conformers of the dipeptides HisGly and GlyHis and of their sodium ion complexes in the gas phase. Phys Chem Chem Phys. 2005 Nov 7;7(21):3744-55. Epub 2005 Sep 9. [PubMed:16358024 ]
- Wickrama Arachchilage AP, Wang F, Feyer V, Plekan O, Prince KC: Photoelectron spectra and structures of three cyclic dipeptides: PhePhe, TyrPro, and HisGly. J Chem Phys. 2012 Mar 28;136(12):124301. doi: 10.1063/1.3693763. [PubMed:22462851 ]
- Tesfai TM, Green BJ, Margerum DW: Decomposition kinetics of Ni(III)-peptide complexes with histidine and histamine as the third residue. Inorg Chem. 2004 Oct 18;43(21):6726-33. [PubMed:15476372 ]
- Hanaki A, Odani A: Transport of Cu(II) from an albumin mimic peptide, GlyGlyHisGly, to histidine and penicillamine. J Inorg Biochem. 2007 Oct;101(10):1428-37. Epub 2007 Jun 12. [PubMed:17643491 ]
- Burke SK, Xu Y, Margerum DW: Cu(II)Gly2HisGly oxidation by H2O2/ascorbic acid to the CuIII complex and its subsequent decay to alkene peptides. Inorg Chem. 2003 Sep 22;42(19):5807-17. [PubMed:12971748 ]
- Green BJ, Tesfai TM, Margerum DW: Nickel(III) oxidation of its glycylglycylhistamine complex. Dalton Trans. 2004 Nov 7;(21):3508-14. Epub 2004 Sep 20. [PubMed:15510270 ]
|
PMID: 9630361