Aminohippuric acid (CED0007280)

Record Information
Version1.0
Creation Date2016-05-22 03:37:06 UTC
Update Date2026-08-25 07:37:40 UTC
Accession NumberCHEM016561
Identification
Common NameAminohippuric acid
ClassSmall Molecule
Description
Aminohippuric acid (C9H10N2O3) is a compound with an average molecular weight of 194.19 g/mol. Aminohippuric acid belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It functions biologically as an endocrine disruptor (PMC11994996) and acts as an inhibitor of the protein target Organic anion transporter 3 (SLC22A8). The compound is found in or released from nine recorded sources, including electrical and electronic equipment such as hybrid capacitors, electrodes, television systems, conductive bodies characterized by conductive materials, and electrically stimulated smoking devices. Other sources include food preservation, unclassified diagnostic agents in healthcare, pharmaceuticals and veterinary products, and household cleaning and consumer products such as tobacco smoke filters and non-electric simulated smoking devices. Recorded exposure routes include intravenous administration, as well as inhalation (PMC3114816, PMC4492867) and smoking (PMC4543297, PMC9969860). Aminohippuric acid is associated with several health effects. It is linked to atherosclerosis (PMC11083012), arthritis (PMC11382499), heart disease (PMC11382499), hypertension (PMC11382499), obesity (PMC9977221), lung disease (PMC6521202), cataract (PMC12316782), and melanoma (PMC8458058). It is associated with an increase in inflammation (PMC11946043, PMC6054606), stroke (PMC10946040), breast cancer (PMC5581466), pancreatic cancer (PMC9600415), skin cancer (PMC12316782), and lung cancer (PMC12316782, PMC3017938, PMC3384073). It is further associated with depression (PMC11382499, PMC13224428) and anxiety (PMC13224428), while a decrease in cancer is noted (PMC11298429, PMC13215396, PMC3114816, PMC5509823). Additionally, it is elevated in the urine of those with male infertility (PMC11946043).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
Aminohippuric acidChEBI
N-(p-Aminobenzoyl)aminoacetic acidChEBI
N-(p-Aminobenzoyl)glycineChEBI
N-(Para-aminobenzoyl)glycineChEBI
p-AminohippurateChEBI
PAHChEBI
PahaChEBI
Para-aminohippuric acidChEBI
Paraaminohippuric acidChEBI
p-Aminohippuric acidKegg
AminohippateGenerator
Aminohippic acidGenerator
N-(p-Aminobenzoyl)aminoacetateGenerator
Para-aminohippateGenerator
Para-aminohippic acidGenerator
ParaaminohippateGenerator
Paraaminohippic acidGenerator
p-AminohippateGenerator
p-Aminohippic acidGenerator
4-AminohippateGenerator
4-Aminohippic acidGenerator
4-AminohippurateHMDB
AminohippurateHMDB
ChlorphentermineHMDB
N-(4-Aminobenzoyl)glycineHMDB
NefrotestHMDB
Para-aminohippurateHMDB
Aminohippurate sodiumHMDB
Sodium para-aminohippurateHMDB
Sodium, aminohippurateHMDB
p AminohippurateHMDB
Para-aminohippurate, sodiumHMDB
Para aminohippuric acidHMDB
4 Aminohippuric acidHMDB
NephrotestHMDB
Sodium para aminohippurateHMDB
p Aminohippuric acidHMDB
4-Aminohippuric acidChEBI
Chemical FormulaC9H10N2O3
Average Molecular Mass194.187 g/mol
Monoisotopic Mass194.069 g/mol
CAS Registry Number61-78-9
IUPAC Name2-[(4-aminophenyl)formamido]acetic acid
Traditional Nameaminohippurate
SMILESNC1=CC=C(C=C1)C(=O)NCC(O)=O
InChI IdentifierInChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)
InChI KeyHSMNQINEKMPTIC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.13 g/LALOGPS
logP0ALOGPS
logP-1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.7ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.82 m³·mol⁻¹ChemAxon
Polarizability19.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0006-0910000000-d6e2bf0631a469ca607bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-3900000000-454a970609f4250f1022Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-0910000000-d6e2bf0631a469ca607bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-2900000000-13545b50126e3469611dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dl-5930000000-96c158cb0933998c6b3eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f77-2900000000-a8b8a25d88057ce84dd4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-2900000000-010a61221aacb1a4cd70Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02fx-9200000000-507831f6ef0e0b10b17aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-2900000000-5507cabf47dd4ffa240eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9100000000-c8d97f1cc97cffcbe56fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-395b484545b8358e9937Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-fe5d8f1224f0bd9ade27Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-ccbc2ae9fc7edc68395fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-bcd0e15e018677f4d5ceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-53a86daaf93d39923f6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-50659a062cb251ecd11dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006x-9600000000-b0f0d35bf4f1f7ac6cabNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-9100000000-3af1801b411555af00c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-0900000000-886d3df0d88886b514f5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-1900000000-017f11bcb65dee99bf7eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9400000000-7ee96554ee69d820a99cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-fea9a305d118ff5d8f9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2900000000-4180dbe6449997335b79Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9200000000-6c147308d50977004a22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-c1f1f8223fde58be726fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-e900ce261e7b036f230aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9100000000-575f1135c946d9802884Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-2900000000-30ea092962a8f3debe62Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-11054566f6cbc98039ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-eef4c1f804c025cbb978Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2761.0Log mg/kg[1600:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
arthritisassociated_withNot AvailablePMC11382499
lung cancerassociated_withNot AvailablePMC12316782 , PMC3017938 , PMC3384073
hypertensionassociated_withNot AvailablePMC11382499
inflammationassociated_withincreasePMC11946043 , PMC6054606
cancerassociated_withdecreasePMC11298429 , PMC13215396 , PMC3114816 , PMC5509823
breast cancerassociated_withincreasePMC5581466
strokeassociated_withincreasePMC10946040
melanomaassociated_withNot AvailablePMC8458058
anxietyassociated_withNot AvailablePMC13224428
depressionassociated_withNot AvailablePMC11382499 , PMC13224428
obesityassociated_withNot AvailablePMC9977221
atherosclerosisassociated_withNot AvailablePMC11083012
heart diseaseassociated_withNot AvailablePMC11382499
male infertilityelevated_in_urine_inincreasePMC11946043
skin cancerassociated_withincreasePMC12316782
pancreatic cancerassociated_withincreasePMC9600415
cataractassociated_withNot AvailablePMC12316782
lung diseaseassociated_withNot AvailablePMC6521202
anovulationassociated_withNot AvailablePMC11946043
Exposure Sources
Source IDSourceSectorReference
411Unclassified diagnostic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)95.8324
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)1.40129
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)122.223
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)7.94062
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)216.577
Click to view 3D structureSolute carrier family 22 member 6Q8VC69Mus musculusPredicted (SEA)0.0778492
Neprilysin structureClick to view 3D structureNeprilysinP08473HumansPredicted (SEA)36.9784
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)222.96
Click to view 3D structureProlyl hydroxylase EGLN3Q9H6Z9HumansPredicted (SEA)4.67095
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)48.7336
Click to view 3D structureProlyl 4-hydroxylaseQ84406Paramecium bursaria Chlorella virus 1Predicted (SEA)2.95827
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)194.701
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)201.474
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)177.029
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)193.144
Protective antigen structureClick to view 3D structureProtective antigenP13423Bacillus anthracisPredicted (SEA)16.7376
Procathepsin L structureClick to view 3D structureProcathepsin LP07711HumansPredicted (SEA)195.402
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)185.048
Click to view 3D structureProlyl 4-hydroxylase subunit alpha-1P54001Rattus norvegicusPredicted (SEA)0.0778492
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)302.678
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)837.346
Click to view 3D structureEgl nine homolog 1P59722Rattus norvegicusPredicted (SEA)1.79053
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)571.725
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)728.124
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)178.197
Concentrations
Not Available
External Links
DrugBank IDDB00345
HMDB IDHMDB0001867
FooDB IDFDB022720
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6359
PDB IDNot Available
Wikipedia LinkAminohippuric_Acid
Chemspider ID2063
ChEBI ID104011
PubChem Compound ID2148
Kegg Compound IDD06890
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barnabei, Ottavio; Cocito, Carlo. Synthesis of p-aminohippuric acid in presence of thyroxine and a hepatic factor. Ricerca sci. (1955), 25 3329-32.
2. Barnabei, Ottavio; Cocito, Carlo. Synthesis of p-aminohippuric acid in presence of thyroxine and a hepatic factor. Ricerca sci. (1955), 25 3329-32.
3. Giudice PL, Dubourg L, Hadj-Aissa A, Said MH, Claris O, Audra P, Martin X, Cochat P: Renal function of children exposed to cyclosporin in utero. Nephrol Dial Transplant. 2000 Oct;15(10):1575-9.
4. Devaux S, Gellert S, Streichan F: [A new method for the determination of the maximal tubular transport of p-aminohippuric acid without urine analysis in children with transplanted kidney]. Z Urol Nephrol. 1984 Nov;77(11):639-46.
5. Gunston KD, Davey DD: The association between measured and clinically assessed amniotic fluid volume and fetal growth and nutrition. S Afr Med J. 1978 Sep 16;54(12):499-500.
6. van Otterlo LC, Wladimiroff JW, Wallenburg HC: Relationship between fetal urine production and amniotic fluid volume in normal pregnancy and pregnancy complicated by diabetes. Br J Obstet Gynaecol. 1977 Mar;84(3):205-9.
7. Malek RS, Wilkiemeyer RM, Boyce WH: The stone-forming kidney: a study of functional differences between individual kidneys in idiopathic renal lithiasis. J Urol. 1976 Jul;116(1):11-4.
8. Stanley AJ, Forrest EH, Dabos K, Bouchier IA, Hayes PC: Natriuretic effect of an adenosine-1 receptor antagonist in cirrhotic patients with ascites. Gastroenterology. 1998 Aug;115(2):406-11.
9. Daniel SS, James LS, Strauss J: Response to rapid volume expansion during the postnatal period. Pediatrics. 1981 Dec;68(6):809-13.
10. Strauss J, Daniel SS, James LS: Postnatal adjustment in renal function. Pediatrics. 1981 Dec;68(6):802-8.
11. Edlund A, Ohlsen H, Sollevi A: Renal effects of local infusion of adenosine in man. Clin Sci (Lond). 1994 Aug;87(2):143-9.
12. Burckhardt G, Bahn A, Wolff NA: Molecular physiology of renal p-aminohippurate secretion. News Physiol Sci. 2001 Jun;16:114-8.
13. Izzedine H, Launay-Vacher V, Isnard-Bagnis C, Deray G: Drug-induced Fanconi's syndrome. Am J Kidney Dis. 2003 Feb;41(2):292-309.
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=11007824
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=11060218
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=11078692
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=11443229
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=12523660
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=12552490
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=16169291
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=19309105
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=20439170
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22036005
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22273603
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22406909
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=22460716
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=2496229
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=6395558
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=7198774
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=7198775
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=734583
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=7924159
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=843496
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=933268
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=9679046