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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:20 UTC
Update Date2021-09-14 15:45:45 UTC
HMDB IDHMDB0029008
Secondary Accession Numbers
  • HMDB29008
Metabolite Identification
Common NamePhenylalanylvaline
DescriptionPhenylalanylvaline is a dipeptide composed of phenylalanine and valine. 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?1582753365
Synonyms
ValueSource
F-VChEBI
FVChEBI
L-Phe-L-valChEBI
F-V DipeptideHMDB
FV DipeptideHMDB
L-Phenylalanyl-L-valineHMDB
N-L-Phenylalanyl-L-valineHMDB
N-PhenylalanylvalineHMDB
Phe-valHMDB
Phenylalanine valine dipeptideHMDB
Phenylalanine-valine dipeptideHMDB
Phenylalanyl-valineHMDB
PhenylalanylvalineChEBI
Chemical FormulaC14H20N2O3
Average Molecular Weight264.325
Monoisotopic Molecular Weight264.147392512
IUPAC Name(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-methylbutanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-methylbutanoic acid
CAS Registry Number3918-90-9
SMILES
CC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C14H20N2O3/c1-9(2)12(14(18)19)16-13(17)11(15)8-10-6-4-3-5-7-10/h3-7,9,11-12H,8,15H2,1-2H3,(H,16,17)(H,18,19)/t11-,12-/m0/s1
InChI KeyIEHDJWSAXBGJIP-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
  • Valine 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
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic salt
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Organic zwitterion
  • 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
LogP-0.84Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.2 g/LALOGPS
logP-0.87ALOGPS
logP-0.84ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.41 m³·mol⁻¹ChemAxon
Polarizability28.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+165.66130932474
DeepCCS[M-H]-163.30330932474
DeepCCS[M-2H]-196.18930932474
DeepCCS[M+Na]+171.75430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenylalanylvalineCC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O3485.4Standard polar33892256
PhenylalanylvalineCC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O2010.8Standard non polar33892256
PhenylalanylvalineCC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(O)=O2212.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylalanylvaline,1TMS,isomer #1CC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C2159.8Semi standard non polar33892256
Phenylalanylvaline,1TMS,isomer #2CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O2212.8Semi standard non polar33892256
Phenylalanylvaline,1TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2135.7Semi standard non polar33892256
Phenylalanylvaline,2TMS,isomer #1CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O[Si](C)(C)C2199.0Semi standard non polar33892256
Phenylalanylvaline,2TMS,isomer #1CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)C(=O)O[Si](C)(C)C2201.3Standard non polar33892256
Phenylalanylvaline,2TMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2117.9Semi standard non polar33892256
Phenylalanylvaline,2TMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2188.4Standard non polar33892256
Phenylalanylvaline,2TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2188.2Semi standard non polar33892256
Phenylalanylvaline,2TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C)[Si](C)(C)C2227.1Standard non polar33892256
Phenylalanylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2357.9Semi standard non polar33892256
Phenylalanylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2257.3Standard non polar33892256
Phenylalanylvaline,3TMS,isomer #1CC(C)[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)C2180.2Semi standard non polar33892256
Phenylalanylvaline,3TMS,isomer #1CC(C)[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)C2283.1Standard non polar33892256
Phenylalanylvaline,3TMS,isomer #2CC(C)[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)C2324.6Semi standard non polar33892256
Phenylalanylvaline,3TMS,isomer #2CC(C)[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)C2324.2Standard non polar33892256
Phenylalanylvaline,3TMS,isomer #3CC(C)[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)C2315.7Semi standard non polar33892256
Phenylalanylvaline,3TMS,isomer #3CC(C)[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)C2362.3Standard non polar33892256
Phenylalanylvaline,4TMS,isomer #1CC(C)[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)C2360.6Semi standard non polar33892256
Phenylalanylvaline,4TMS,isomer #1CC(C)[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)C2418.7Standard non polar33892256
Phenylalanylvaline,1TBDMS,isomer #1CC(C)[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2419.1Semi standard non polar33892256
Phenylalanylvaline,1TBDMS,isomer #2CC(C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C)C(=O)O2426.5Semi standard non polar33892256
Phenylalanylvaline,1TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2381.6Semi standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #1CC(C)[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)C2635.0Semi standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #1CC(C)[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)C2590.2Standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #2CC(C)[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)C2615.5Semi standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #2CC(C)[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)C2579.5Standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #3CC(C)[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)C2647.7Semi standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #3CC(C)[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)C2604.3Standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #4CC(C)[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)O2786.7Semi standard non polar33892256
Phenylalanylvaline,2TBDMS,isomer #4CC(C)[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)O2622.1Standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #1CC(C)[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)C2849.0Semi standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #1CC(C)[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)C2826.8Standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #2CC(C)[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)C3006.8Semi standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #2CC(C)[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)C2850.3Standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #3CC(C)[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)C3005.9Semi standard non polar33892256
Phenylalanylvaline,3TBDMS,isomer #3CC(C)[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)C2880.2Standard non polar33892256
Phenylalanylvaline,4TBDMS,isomer #1CC(C)[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)C3219.0Semi standard non polar33892256
Phenylalanylvaline,4TBDMS,isomer #1CC(C)[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)C3092.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylalanylvaline 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 - Phenylalanylvaline 10V, Positive-QTOFsplash10-01b9-1980000000-412d0ec298d1b6026d3e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylvaline 20V, Positive-QTOFsplash10-006x-8900000000-6a75d317cfa9fa572cd12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylvaline 40V, Positive-QTOFsplash10-0096-9600000000-cf06cfa15e9e25136a412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylvaline 10V, Negative-QTOFsplash10-03di-0090000000-b7c71fa74fc8ffccaeab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylvaline 20V, Negative-QTOFsplash10-00kf-7970000000-0c0785aee2bc8add13b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylvaline 40V, Negative-QTOFsplash10-002f-9400000000-568179886d37f352ae6c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal 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 IDFDB112024
KNApSAcK IDNot Available
Chemspider ID5685589
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7359121
PDB IDNot Available
ChEBI ID73638
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. Demeshkina N, Repkova M, Ven'yaminova A, Graifer D, Karpova G: Nucleotides of 18S rRNA surrounding mRNA codons at the human ribosomal A, P, and E sites: a crosslinking study with mRNA analogs carrying an aryl azide group at either the uracil or the guanine residue. RNA. 2000 Dec;6(12):1727-36. [PubMed:11142373 ]