Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2016-10-26 16:26:49 UTC
Update Date2021-09-14 15:41:37 UTC
HMDB IDHMDB0062175
Secondary Accession Numbers
  • HMDB62175
Metabolite Identification
Common NameN-Lactoylphenylalanine
DescriptionN-Lactoylphenylalanine is a lactoyl derivative of phenylalanine. N-Lactoyl-amino acids are ubiquitous pseudodipeptides of lactic acid and amino acids that are rapidly formed by reverse proteolysis. A protease, cytosolic nonspecific dipeptidase 2 (CNDP2), catalyzes their formation. The plasma levels of these metabolites strongly correlate with plasma levels of lactate and amino acid (PMID: 25964343 ).
Structure
Data?1563866275
Synonyms
ValueSource
(2S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-3-phenylpropanoateGenerator
N-Lactoyl-phenylalanineHMDB
Chemical FormulaC12H15NO4
Average Molecular Weight237.255
Monoisotopic Molecular Weight237.100107967
IUPAC Name(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid
Traditional Name(2S)-2-[(2S)-2-hydroxypropanamido]-3-phenylpropanoic acid
CAS Registry Number183241-73-8
SMILES
C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C12H15NO4/c1-8(14)11(15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,15)(H,16,17)/t8-,10-/m0/s1
InChI KeyIIRJJZHHNGABMQ-WPRPVWTQSA-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
  • N-acyl-l-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP0.47ALOGPS
logP0.65ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.76 m³·mol⁻¹ChemAxon
Polarizability24.09 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
DeepCCS[M+H]+156.80830932474
DeepCCS[M-H]-154.41230932474
DeepCCS[M-2H]-187.3430932474
DeepCCS[M+Na]+162.78130932474
AllCCS[M+H]+154.832859911
AllCCS[M+H-H2O]+151.132859911
AllCCS[M+NH4]+158.232859911
AllCCS[M+Na]+159.132859911
AllCCS[M-H]-154.332859911
AllCCS[M+Na-2H]-154.632859911
AllCCS[M+HCOO]-155.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-LactoylphenylalanineC[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O3630.9Standard polar33892256
N-LactoylphenylalanineC[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O1843.8Standard non polar33892256
N-LactoylphenylalanineC[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O2013.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Lactoylphenylalanine,1TMS,isomer #1C[C@H](O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O2038.4Semi standard non polar33892256
N-Lactoylphenylalanine,1TMS,isomer #2C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C1989.0Semi standard non polar33892256
N-Lactoylphenylalanine,1TMS,isomer #3C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C1974.6Semi standard non polar33892256
N-Lactoylphenylalanine,2TMS,isomer #1C[C@H](O[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C2035.9Semi standard non polar33892256
N-Lactoylphenylalanine,2TMS,isomer #2C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C2029.0Semi standard non polar33892256
N-Lactoylphenylalanine,2TMS,isomer #3C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C1984.6Semi standard non polar33892256
N-Lactoylphenylalanine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2050.7Semi standard non polar33892256
N-Lactoylphenylalanine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2110.5Standard non polar33892256
N-Lactoylphenylalanine,3TMS,isomer #1C[C@H](O[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2338.3Standard polar33892256
N-Lactoylphenylalanine,1TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O2280.1Semi standard non polar33892256
N-Lactoylphenylalanine,1TBDMS,isomer #2C[C@H](O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2241.2Semi standard non polar33892256
N-Lactoylphenylalanine,1TBDMS,isomer #3C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C2227.6Semi standard non polar33892256
N-Lactoylphenylalanine,2TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2512.7Semi standard non polar33892256
N-Lactoylphenylalanine,2TBDMS,isomer #2C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C2514.8Semi standard non polar33892256
N-Lactoylphenylalanine,2TBDMS,isomer #3C[C@H](O)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2482.2Semi standard non polar33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2733.3Semi standard non polar33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2712.2Standard non polar33892256
N-Lactoylphenylalanine,3TBDMS,isomer #1C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2695.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Lactoylphenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9410000000-0cd8bc043bded37b30282017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Lactoylphenylalanine GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-8962000000-d40495ad1a3b7f9041552017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Lactoylphenylalanine 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 - N-Lactoylphenylalanine 10V, Positive-QTOFsplash10-00du-3690000000-fe5efaae7d2bebb9789f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Positive-QTOFsplash10-00dl-4930000000-41557da015fa2684948e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Positive-QTOFsplash10-0006-9400000000-058c16babbf8853354782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Negative-QTOFsplash10-000i-1390000000-0316182060d4be2e1cc62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Negative-QTOFsplash10-022l-4930000000-892857fde979d59807522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Negative-QTOFsplash10-00di-9500000000-a13bb3961f97b3bfd4f02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Positive-QTOFsplash10-00y0-0930000000-3c841a42eb530533b34d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Positive-QTOFsplash10-00di-1900000000-6f6baa05d00f1f797f8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Positive-QTOFsplash10-00di-5900000000-8e5673adb13e6b5047b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 10V, Negative-QTOFsplash10-000i-4290000000-19943ccd0c8992a79bfe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 20V, Negative-QTOFsplash10-0006-9600000000-77641d15cd4aec9dc2db2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Lactoylphenylalanine 40V, Negative-QTOFsplash10-0f6x-9700000000-47c4e820924a31ceb6c52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11075454
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 References
  1. Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]