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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:19 UTC
Update Date2021-09-14 15:46:18 UTC
HMDB IDHMDB0029001
Secondary Accession Numbers
  • HMDB29001
Metabolite Identification
Common NamePhenylalanylmethionine
DescriptionPhenylalanylmethionine is a dipeptide composed of phenylalanine and methionine. 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?1582753364
Synonyms
ValueSource
FMChEBI
L-Phe-L-metChEBI
Phenylalanyl-methionineChEBI
F-m DipeptideHMDB
FM DipeptideHMDB
L-Phenylalanyl-L-methionineHMDB
N-L-Phenylalanyl-L-methionineHMDB
N-PhenylalanylmethionineHMDB
Phe-metHMDB
Phenylalanine methionine dipeptideHMDB
Phenylalanine-methionine dipeptideHMDB
PhenylalanylmethionineHMDB, ChEBI
Chemical FormulaC14H20N2O3S
Average Molecular Weight296.39
Monoisotopic Molecular Weight296.119463686
IUPAC Name(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
CAS Registry Number15080-84-9
SMILES
CSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C14H20N2O3S/c1-20-8-7-12(14(18)19)16-13(17)11(15)9-10-5-3-2-4-6-10/h2-6,11-12H,7-9,15H2,1H3,(H,16,17)(H,18,19)/t11-,12-/m0/s1
InChI KeyPYOHODCEOHCZBM-RYUDHWBXSA-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
  • Methionine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Aralkylamine
  • Thia fatty acid
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Sulfenyl compound
  • Thioether
  • Dialkylthioether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic zwitterion
  • Hydrocarbon derivative
  • Organic salt
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.07Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP10(-0.01) g/LALOGPS
logP10(-1.1) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.5 m³·mol⁻¹ChemAxon
Polarizability31.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenylalanylmethionineCSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O3657.6Standard polar33892256
PhenylalanylmethionineCSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O2352.2Standard non polar33892256
PhenylalanylmethionineCSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O2598.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylalanylmethionine,1TMS,isomer #1CSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C2504.7Semi standard non polar33892256
Phenylalanylmethionine,1TMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O2546.3Semi standard non polar33892256
Phenylalanylmethionine,1TMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2457.4Semi standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #1CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O[Si](C)(C)C2524.3Semi standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #1CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O[Si](C)(C)C2459.2Standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #2CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2418.8Semi standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #2CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2443.3Standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2491.5Semi standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2501.6Standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #4CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2655.2Semi standard non polar33892256
Phenylalanylmethionine,2TMS,isomer #4CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2530.8Standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2466.3Semi standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2533.7Standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2620.6Semi standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2586.7Standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2585.1Semi standard non polar33892256
Phenylalanylmethionine,3TMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2627.7Standard non polar33892256
Phenylalanylmethionine,4TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2624.5Semi standard non polar33892256
Phenylalanylmethionine,4TMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2657.4Standard non polar33892256
Phenylalanylmethionine,1TBDMS,isomer #1CSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2764.2Semi standard non polar33892256
Phenylalanylmethionine,1TBDMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)C(=O)O2766.9Semi standard non polar33892256
Phenylalanylmethionine,1TBDMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2702.2Semi standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #1CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2997.4Semi standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #1CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2851.8Standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #2CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2944.3Semi standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #2CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2839.3Standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2965.4Semi standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2866.8Standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #4CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3124.1Semi standard non polar33892256
Phenylalanylmethionine,2TBDMS,isomer #4CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2895.1Standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3167.8Semi standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3065.9Standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3333.6Semi standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #2CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3112.2Standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3306.3Semi standard non polar33892256
Phenylalanylmethionine,3TBDMS,isomer #3CSCC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3132.3Standard non polar33892256
Phenylalanylmethionine,4TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3515.7Semi standard non polar33892256
Phenylalanylmethionine,4TBDMS,isomer #1CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3316.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylalanylmethionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylalanylmethionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 10V, Positive-QTOFsplash10-0002-0490000000-3f4c5b9c1cb7495014252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 20V, Positive-QTOFsplash10-00dl-4930000000-ddf82778f7db0944771a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 40V, Positive-QTOFsplash10-0006-9400000000-46952f6f72dede7552942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 10V, Negative-QTOFsplash10-0002-0090000000-e099b0c2c64ddee9c4f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 20V, Negative-QTOFsplash10-0002-9270000000-09d4a94f55ce6b7b49cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylmethionine 40V, Negative-QTOFsplash10-0002-9300000000-c07bf6a535f5ecc33a482021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
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)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 IDFDB112019
KNApSAcK IDNot Available
Chemspider ID5374072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7010505
PDB IDNot Available
ChEBI ID74719
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. Anderson L, Bussler B, Martins H, Dufton M: Enkephalin-processing oligopeptidases in cobra venom: inhibition by thiorphan and bestatin reveals co-operative actions. Toxicon. 1998 May;36(5):719-28. [PubMed:9655632 ]