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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:53 UTC
Update Date2020-02-26 21:42:31 UTC
HMDB IDHMDB0028889
Secondary Accession Numbers
  • HMDB28889
Metabolite Identification
Common NameHistidylleucine
DescriptionHistidylleucine is a dipeptide composed of histidine and leucine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753351
Synonyms
ValueSource
HistidylleucineChEBI
HLChEBI
L-His-L-leuChEBI
N-L-Histidyl-L-leucineChEBI
N-L-Histidyl-L-leucinKegg
H-L dipeptideHMDB
HL dipeptideHMDB
His-LeuHMDB
Histidine leucine dipeptideHMDB
Histidine-leucine dipeptideHMDB
Histidinyl-leucineHMDB
HistidinylleucineHMDB
Histidyl-leucineHMDB
L-Histidinyl-L-leucineHMDB
L-Histidyl-L-leucineHMDB
N-HistidinylleucineHMDB
N-HistidylleucineHMDB
N-L-Histidinyl-L-leucineHMDB
Chemical FormulaC12H20N4O3
Average Molecular Weight268.317
Monoisotopic Molecular Weight268.15354052
IUPAC Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-4-methylpentanoic acid
Traditional NameHis-Leu
CAS Registry Number7763-65-7
SMILES
CC(C)C[C@H](NC(=O)[C@@H](N)CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C12H20N4O3/c1-7(2)3-10(12(18)19)16-11(17)9(13)4-8-5-14-6-15-8/h5-7,9-10H,3-4,13H2,1-2H3,(H,14,15)(H,16,17)(H,18,19)/t9-,10-/m0/s1
InChI KeyMMFKFJORZBJVNF-UWVGGRQHSA-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
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Fatty amide
  • Fatty acyl
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • 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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.85Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility3.3 g/LALOGPS
logP-2.1ALOGPS
logP-2.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.46 m³·mol⁻¹ChemAxon
Polarizability28.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID164234
KEGG Compound IDC05010
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound189008
PDB IDNot Available
ChEBI ID5729
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nath M, Singh H, Eng G, Song X: New diorganotin(IV) derivatives of dipeptides: synthesis and characteristic spectral studies. Spectrochim Acta A Mol Biomol Spectrosc. 2008 Nov 15;71(2):529-36. doi: 10.1016/j.saa.2008.01.006. Epub 2008 Jan 11. [PubMed:18289925 ]
  2. Reddy PR, Manjula P: Mixed-ligand copper(II)-phenanthroline-dipeptide complexes: synthesis, characterization, and DNA-cleavage properties. Chem Biodivers. 2007 Mar;4(3):468-80. [PubMed:17372949 ]
  3. Wang X, Fukuoka S, Tsukigawara R, Nagata K, Higuchi M: Electric-field-enhanced oriented cobalt coordinated peptide monolayer and its electrochemical properties. J Colloid Interface Sci. 2013 Jan 15;390(1):54-61. doi: 10.1016/j.jcis.2012.08.079. Epub 2012 Oct 8. [PubMed:23102909 ]
  4. Reddy PR, Rao KS: Ternary nickel(II) complexes as hydrolytic DNA-cleavage agents. Chem Biodivers. 2006 Feb;3(2):231-44. [PubMed:17193262 ]
  5. Grima M, Anjuere J, Ingert C, Coquard C, Steger J, Barthelmebs M, Imbs JL: [Effect of a non-antihypertensive dose of ramipril on the plasma and tissue renin-angiotensin system in 27 TGR (mRen2) rats]. Arch Mal Coeur Vaiss. 2001 Aug;94(8):805-12. [PubMed:11575208 ]