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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-08 21:40:45 UTC
Update Date2023-02-21 17:18:41 UTC
HMDB IDHMDB0029223
Secondary Accession Numbers
  • HMDB29223
Metabolite Identification
Common Namealpha-Methylphenylalanine
Descriptionalpha-Methylphenylalanine, also known as α-methyl-DL-phenylalanine, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Based on a literature review a significant number of articles have been published on alpha-Methylphenylalanine.
Structure
Data?1676999921
Synonyms
ValueSource
a-MethylphenylalanineGenerator
Α-methylphenylalanineGenerator
2-Amino-2-methyl-3-phenylpropanoateHMDB
alpha-Methylphenylalanine, hydrochloride, (D-phe)-isomerHMDB
alpha-Methylphenylalanine, hydrochloride, (DL-phe)-isomerHMDB
alpha-Methylphenylalanine, hydrochloride, (L-phe)-isomerHMDB
alpha-Methylphenylalanine, (D-phe)-isomerHMDB
alpha-Methylphenylalanine, (DL-phe)-isomerHMDB
alpha-Methylphenylalanine, (L-phe)-isomerHMDB
a-Methyl-DL-phenylalanineHMDB
Α-methyl-DL-phenylalanineHMDB
alpha-MethylphenylalanineMeSH
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name2-amino-2-methyl-3-phenylpropanoic acid
Traditional Name2-amino-2-methyl-3-phenylpropanoic acid
CAS Registry NumberNot Available
SMILES
CC(N)(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13)
InChI KeyHYOWVAAEQCNGLE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
PropertyValueSource
Water Solubility5 g/LALOGPS
logP-1ALOGPS
logP-0.75ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability18.86 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
DarkChem[M+H]+140.66631661259
DarkChem[M-H]-135.73531661259
DeepCCS[M+H]+136.14730932474
DeepCCS[M-H]-132.3230932474
DeepCCS[M-2H]-169.69130932474
DeepCCS[M+Na]+145.2330932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.232859911
AllCCS[M-H]-139.632859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-141.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-MethylphenylalanineCC(N)(CC1=CC=CC=C1)C(O)=O2633.3Standard polar33892256
alpha-MethylphenylalanineCC(N)(CC1=CC=CC=C1)C(O)=O1449.2Standard non polar33892256
alpha-MethylphenylalanineCC(N)(CC1=CC=CC=C1)C(O)=O1676.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Methylphenylalanine,1TMS,isomer #1CC(N)(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C1565.1Semi standard non polar33892256
alpha-Methylphenylalanine,1TMS,isomer #2CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O1648.7Semi standard non polar33892256
alpha-Methylphenylalanine,2TMS,isomer #1CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1643.2Semi standard non polar33892256
alpha-Methylphenylalanine,2TMS,isomer #1CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1686.1Standard non polar33892256
alpha-Methylphenylalanine,2TMS,isomer #2CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1840.4Semi standard non polar33892256
alpha-Methylphenylalanine,2TMS,isomer #2CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1766.1Standard non polar33892256
alpha-Methylphenylalanine,3TMS,isomer #1CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1860.0Semi standard non polar33892256
alpha-Methylphenylalanine,3TMS,isomer #1CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1828.0Standard non polar33892256
alpha-Methylphenylalanine,1TBDMS,isomer #1CC(N)(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C1812.7Semi standard non polar33892256
alpha-Methylphenylalanine,1TBDMS,isomer #2CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O1899.9Semi standard non polar33892256
alpha-Methylphenylalanine,2TBDMS,isomer #1CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2109.0Semi standard non polar33892256
alpha-Methylphenylalanine,2TBDMS,isomer #1CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2104.8Standard non polar33892256
alpha-Methylphenylalanine,2TBDMS,isomer #2CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2302.8Semi standard non polar33892256
alpha-Methylphenylalanine,2TBDMS,isomer #2CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2173.5Standard non polar33892256
alpha-Methylphenylalanine,3TBDMS,isomer #1CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2532.8Semi standard non polar33892256
alpha-Methylphenylalanine,3TBDMS,isomer #1CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2415.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-8693856b7ebd46028a632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9500000000-1c0774497a68191729b12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Positive-QTOFsplash10-001i-0900000000-0f6eecd6cec27b5466002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Positive-QTOFsplash10-001i-2900000000-c5666ae92da7850e89fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Positive-QTOFsplash10-0006-9400000000-24d32f10a470e037f6cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Negative-QTOFsplash10-004i-0900000000-b095d20c24fa61b85a402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Negative-QTOFsplash10-005i-6900000000-b6240b2bfb4f9701787c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Negative-QTOFsplash10-00l6-8900000000-bbd41f94a7130dcb20772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Negative-QTOFsplash10-004l-3900000000-13907a76b4a5975aee8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Negative-QTOFsplash10-014i-4900000000-a58fdc5f38658c886c762021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Negative-QTOFsplash10-014l-9700000000-17cd851b9dd640f259612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Positive-QTOFsplash10-001i-1900000000-490c647484a64a1b4bd32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Positive-QTOFsplash10-014i-2900000000-4cfbe93b4c0531391d9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Positive-QTOFsplash10-0006-9100000000-0be2b8f0f765d186e28e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ID97158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108055
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available