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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:21:34 UTC
Update Date2021-09-26 22:55:21 UTC
HMDB IDHMDB0246331
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Acetylaminohippuric acid
Description4-Acetylaminohippuric acid, also known as 4-acetylaminohippate or PAAHA, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Based on a literature review very few articles have been published on 4-Acetylaminohippuric acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-acetylaminohippuric acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Acetylaminohippuric acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
4-AcetylaminohippateGenerator
4-Acetylaminohippic acidGenerator
N-Acetyl-p-aminohippuric acidHMDB
PAAHAHMDB
Acetyl-pahHMDB
p-Acetylaminohippuric acidHMDB
Para-acetamidohippuric acidHMDB
Chemical FormulaC11H12N2O4
Average Molecular Weight236.227
Monoisotopic Molecular Weight236.079706874
IUPAC Name2-[(4-acetamidophenyl)formamido]acetic acid
Traditional Name[(4-acetamidophenyl)formamido]acetic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NC1=CC=C(C=C1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C11H12N2O4/c1-7(14)13-9-4-2-8(3-5-9)11(17)12-6-10(15)16/h2-5H,6H2,1H3,(H,12,17)(H,13,14)(H,15,16)
InChI KeyVLSCGEIQKZBMEA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Substituents
  • Hippuric acid or derivatives
  • Hippuric acid
  • Acylaminobenzoic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Acetanilide
  • Benzamide
  • N-acetylarylamine
  • Anilide
  • N-arylamide
  • Benzoyl
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen 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
logP0.23ALOGPS
logP-0.24ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.98 m³·mol⁻¹ChemAxon
Polarizability23.52 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]+149.35430932474
DeepCCS[M-H]-146.96530932474
DeepCCS[M-2H]-180.40430932474
DeepCCS[M+Na]+155.41730932474
AllCCS[M+H]+151.932859911
AllCCS[M+H-H2O]+148.332859911
AllCCS[M+NH4]+155.332859911
AllCCS[M+Na]+156.332859911
AllCCS[M-H]-153.832859911
AllCCS[M+Na-2H]-154.132859911
AllCCS[M+HCOO]-154.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Acetylaminohippuric acidCC(=O)NC1=CC=C(C=C1)C(=O)NCC(O)=O3503.5Standard polar33892256
4-Acetylaminohippuric acidCC(=O)NC1=CC=C(C=C1)C(=O)NCC(O)=O2414.3Standard non polar33892256
4-Acetylaminohippuric acidCC(=O)NC1=CC=C(C=C1)C(=O)NCC(O)=O2651.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Acetylaminohippuric acid,2TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C)C=C1)[Si](C)(C)C2455.2Semi standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C)C=C1)[Si](C)(C)C2348.3Standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C)C=C1)[Si](C)(C)C2816.3Standard polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C12583.7Semi standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C12430.3Standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C12998.7Standard polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C1)[Si](C)(C)C2343.5Semi standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C1)[Si](C)(C)C2393.2Standard non polar33892256
4-Acetylaminohippuric acid,2TMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C1)[Si](C)(C)C2835.3Standard polar33892256
4-Acetylaminohippuric acid,3TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2334.9Semi standard non polar33892256
4-Acetylaminohippuric acid,3TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2335.1Standard non polar33892256
4-Acetylaminohippuric acid,3TMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2553.1Standard polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2977.4Semi standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2759.5Standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2941.1Standard polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13158.6Semi standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12802.1Standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #2CC(=O)NC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13081.4Standard polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2890.7Semi standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2759.5Standard non polar33892256
4-Acetylaminohippuric acid,2TBDMS,isomer #3CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2974.5Standard polar33892256
4-Acetylaminohippuric acid,3TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3062.0Semi standard non polar33892256
4-Acetylaminohippuric acid,3TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2893.4Standard non polar33892256
4-Acetylaminohippuric acid,3TBDMS,isomer #1CC(=O)N(C1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2882.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-3910000000-aa5681b6221a749c486e2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylaminohippuric acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 10V, Positive-QTOFsplash10-03di-0950000000-cb0187c4566377b880882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 20V, Positive-QTOFsplash10-0006-0910000000-650a192919ff39e71fa52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 40V, Positive-QTOFsplash10-01c3-6900000000-4041c6437c9e723e61202021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 10V, Negative-QTOFsplash10-00ko-1890000000-9140db59c5ec174d78ce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 20V, Negative-QTOFsplash10-0536-4900000000-79051166512ea548813a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylaminohippuric acid 40V, Negative-QTOFsplash10-00kg-6900000000-bba0ffe777517fc759862021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID141128
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160605
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]