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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-11-30 15:51:35 UTC
Update Date2021-09-14 15:46:19 UTC
HMDB IDHMDB0013243
Secondary Accession Numbers
  • HMDB0028936
  • HMDB13243
  • HMDB28936
Metabolite Identification
Common NameLeucylphenylalanine
DescriptionLeucylphenylalanine, also known as L-F or L-leu-L-phe, 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. Leucylphenylalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make leucylphenylalanine a potential biomarker for the consumption of these foods. Leucylphenylalanine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Leucylphenylalanine.
Structure
Thumb
Synonyms
ValueSource
L-FChEBI
L-Leu-L-pheChEBI
LFChEBI
L-F DipeptideHMDB
L-Leucyl-L-phenylalanineHMDB
LF DipeptideHMDB
Leu-pheHMDB
Leucine phenylalanine dipeptideHMDB
Leucine-phenylalanine dipeptideHMDB
Leucyl-phenylalanineHMDB
N-L-Leucyl-L-phenylalanineHMDB
N-Leucyl-3-phenylalanineHMDB
N-LeucylphenylalanineHMDB
LeucylphenylalanineChEBI
Chemical FormulaC15H22N2O3
Average Molecular Weight278.352
Monoisotopic Molecular Weight278.163042576
IUPAC Name(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid
CAS Registry Number3063-05-6
SMILES
CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C15H22N2O3/c1-10(2)8-12(16)14(18)17-13(15(19)20)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)/t12-,13-/m0/s1
InChI KeyKFKWRHQBZQICHA-STQMWFEESA-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
  • Phenylalanine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Carboxamide group
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Organic zwitterion
  • Organic salt
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.02 umol/mmol creatinineAdult (>18 years old)BothNormal 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 IDFDB111642
KNApSAcK IDNot Available
Chemspider ID5360450
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6992309
PDB IDNot Available
ChEBI ID73585
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sjolinder M, Stenke L, Nasman-Glaser B, Widell S, Doucet J, Jakobsson PJ, Lindgren JA: Aberrant expression of active leukotriene C(4) synthase in CD16(+) neutrophils from patients with chronic myeloid leukemia. Blood. 2000 Feb 15;95(4):1456-64. [PubMed:10666225 ]
  2. Zigmond SH, Tranquillo AW: Chemotactic peptide binding by rabbit polymorphonuclear leukocytes. Presence of two compartments having similar affinities but different kinetics. J Biol Chem. 1986 Apr 25;261(12):5283-8. [PubMed:3957925 ]
  3. Khwaja A, Roberts PJ, Jones HM, Yong K, Jaswon MS, Linch DC: Isoquinolinesulfonamide protein kinase inhibitors H7 and H8 enhance the effects of granulocyte-macrophage colony-stimulating factor (GM-CSE) on neutrophil function and inhibit GM-CSF receptor internalization. Blood. 1990 Sep 1;76(5):996-1003. [PubMed:2168226 ]
  4. Folefoc AT, Fromme BJ, Katz AA, Flanagan CA: South African mutations of the CCR5 coreceptor for HIV modify interaction with chemokines and HIV Envelope protein. J Acquir Immune Defic Syndr. 2010 Aug;54(4):352-9. doi: 10.1097/QAI.0b013e3181e0c7b2. [PubMed:20442662 ]