Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:54 UTC
HMDB IDHMDB0000512
Secondary Accession Numbers
  • HMDB00512
Metabolite Identification
Common NameN-Acetyl-L-phenylalanine
DescriptionN-Acetyl-L-phenylalanine or N-Acetylphenylalanine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-phenylalanine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-phenylalanine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-phenylalanine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylphenylalanine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free phenylalanine can also occur. In particular, N-Acetyl-L-phenylalanine can be biosynthesized from L-phenylalanine and acetyl-CoA by the enzyme phenylalanine N-acetyltransferase (EC 2.3.1.53). N-Acetyl-L-phenylalanine is a potential uremic toxin and is considered as a hazardous amphipathic metabolite of phenylalanine (PMID: 4038506 ). Many N-acetylamino acids, including N-acetylphenylalanine, are classified as uremic toxins (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-Acetyl-L-phenylalanine appears in large amount in urine of patients with phenylketonuria (PKU), which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine (PMID: 3473611 ). N-Acetyl-L-phenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] which is found in the phenylalanine metabolism pathway. N-Acetyl-L-phenylalanine is produced for medical, feed, and nutritional applications such as in the preparation of aspartame. Afalanine (N-Acetyl-DL-phenylalanine) is also approved for use as an antidepressant.
Structure
Data?1676999694
Synonyms
ValueSource
Acetyl-L-phenylalanineChEBI
AcetylphenylalanineChEBI
L-N-AcetylphenylalanineChEBI
N-AcetylphenylalanineChEBI
N-Acetyl-3-phenyl-L-alanineHMDB
N-Acetyl-L-phenalanineHMDB
N-Acetylphenylalanine, (D,L)-isomer, 3H-labeledHMDB
N-Acetylphenylalanine, (L)-isomerHMDB
N-Acetylphenylalanine, (L)-isomer, 3H-labeledHMDB
N-Acetylphenylalanine, (D)-isomerHMDB
Chemical FormulaC11H13NO3
Average Molecular Weight207.2258
Monoisotopic Molecular Weight207.089543287
IUPAC Name(2S)-2-acetamido-3-phenylpropanoic acid
Traditional Nameacetyl-L-phenylalanine
CAS Registry Number2018-61-3
SMILES
CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1
InChI KeyCBQJSKKFNMDLON-JTQLQIEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • 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 Point171 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6450 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.93GREEN,PG ET AL. (1991)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg144.19830932474
[M-H]-Not Available146.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000018
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.11ALOGPS
logP0.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.56 m³·mol⁻¹ChemAxon
Polarizability21.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.23431661259
DarkChem[M-H]-145.20631661259
AllCCS[M+H]+146.55932859911
AllCCS[M-H]-146.37832859911
DeepCCS[M+H]+142.46830932474
DeepCCS[M-H]-140.07330932474
DeepCCS[M-2H]-173.97430932474
DeepCCS[M+Na]+148.67230932474
AllCCS[M+H]+146.632859911
AllCCS[M+H-H2O]+142.632859911
AllCCS[M+NH4]+150.232859911
AllCCS[M+Na]+151.332859911
AllCCS[M-H]-146.432859911
AllCCS[M+Na-2H]-146.932859911
AllCCS[M+HCOO]-147.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-phenylalanineCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O2997.4Standard polar33892256
N-Acetyl-L-phenylalanineCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O1758.7Standard non polar33892256
N-Acetyl-L-phenylalanineCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O1765.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-phenylalanine,1TMS,isomer #1CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C1805.5Semi standard non polar33892256
N-Acetyl-L-phenylalanine,1TMS,isomer #2CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C1800.2Semi standard non polar33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C1799.6Semi standard non polar33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C1862.1Standard non polar33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2182.4Standard polar33892256
N-Acetyl-L-phenylalanine,1TBDMS,isomer #1CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2053.8Semi standard non polar33892256
N-Acetyl-L-phenylalanine,1TBDMS,isomer #2CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C2030.6Semi standard non polar33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2277.7Semi standard non polar33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2293.4Standard non polar33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2455.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (2 TMS)splash10-00kf-3980000000-205dc96635b498baa46c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (1 TMS)splash10-00dl-3920000000-50af7cdc34df34b89e912014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized)splash10-00kf-3980000000-205dc96635b498baa46c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized)splash10-00dl-3920000000-50af7cdc34df34b89e912017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)splash10-0fr7-1950000000-8c9c63efeb473bcf76252017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)splash10-00dl-2920000000-f0ce2160cf1eb9d38d562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)splash10-0f6x-2910000000-33afe725162942dc296a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-2c91eb9a78faef00e1da2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9110000000-e910d5b4824d2e88d6972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-0900000000-9e69c187ac85603658262012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-0900000000-04559809a9c6261f18b62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ufr-5900000000-a8bb0fc573e6143527aa2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0a4i-0090000000-2dcdf0ed503251026e402012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-03di-2920000000-7447f1e30d868cae5af62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0lxy-8900000000-3b53da8f8106adfdd6772012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0pbc-9400000000-1737db9a05bf29f3701a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0a4l-9100000000-f015dd2066ebbefec15a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0a4l-1960000000-20faf15c3d02bbe80ad22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-0900000000-891ecddb54dab32f4dce2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00di-1900000000-6867cba730dee87122652012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00di-2900000000-2e77f5a51bec17ed674e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0udi-4900000000-c9aadc8231b14121aa8c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-02tc-0900000000-ac3b438665d0b035a7e22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0900000000-a426a7fbff06e9213f592012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0900000000-0d8dd7876525745785ff2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0fdo-6900000000-ad4d31f8b5e3e04744162012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ , negative-QTOFsplash10-0a4i-0090000000-2dcdf0ed503251026e402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ , negative-QTOFsplash10-03di-2920000000-7447f1e30d868cae5af62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 10V, Positive-QTOFsplash10-0btc-2950000000-2865ae294df6193f5a752016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 20V, Positive-QTOFsplash10-044l-2900000000-1b1f3d364775a1619b262016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 40V, Positive-QTOFsplash10-0006-9200000000-9bb5ea6eb4c3ab49ee322016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 10V, Negative-QTOFsplash10-0a4i-2890000000-293238d6264d01ab86c42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 20V, Negative-QTOFsplash10-0900-5910000000-b912a04d31d0b03a85522016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 40V, Negative-QTOFsplash10-052f-9200000000-1b69d466f84616cfe6282016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX 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+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 Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 IDFDB022084
KNApSAcK IDNot Available
Chemspider ID67404
KEGG Compound IDC03519
BioCyc IDCPD-439
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5498
PubChem Compound74839
PDB IDNot Available
ChEBI ID16259
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1265531
References
Synthesis ReferenceBorovicka, Milos; Cervinka, Otakar; Gajewski, Karel; Lukac, Juraj. Isolation of optically pure N-acetyl-L-phenylalanine after enantioselective hydrogenation of N-acetamidocinnamic acid. Czech. (1985), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  2. Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. [PubMed:12013218 ]
  3. Mach H, Middaugh CR, Lewis RV: Detection of proteins and phenol in DNA samples with second-derivative absorption spectroscopy. Anal Biochem. 1992 Jan;200(1):20-6. [PubMed:1375815 ]
  4. Okajima K, Inoue M, Morino Y: Studies on the mechanism for renal elimination of N-acetylphenylalanine: its pathophysiologic significance in phenylketonuria. J Lab Clin Med. 1985 Jan;105(1):132-8. [PubMed:4038506 ]
  5. Jellum E, Horn L, Thoresen O, Kvittingen EA, Stokke O: Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolism. Scand J Clin Lab Invest Suppl. 1986;184:21-6. [PubMed:3473611 ]
  6. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  7. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  8. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  9. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  10. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]