P-AMINOBENZOIC ACID (CHEM004699)

Record Information
Version1.0
Creation Date2016-05-19 01:53:47 UTC
Update Date2026-05-14 17:35:22 UTC
Accession NumberCHEM004699
Identification
Common NameP-AMINOBENZOIC ACID
ClassSmall Molecule
Description
An aminobenzoic acid in which the amino group is para to the carboxy group.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Amino-4-carboxybenzeneChEBI
4-Amino-benzoic acidChEBI
4-AminobenzoesaeureChEBI
4-CarboxyanilineChEBI
4-CarboxyphenylamineChEBI
ABEEChEBI
gamma-Aminobenzoic acidChEBI
p-AminobenzoesaeureChEBI
p-CarboxyanilineChEBI
p-CarboxyphenylamineChEBI
PABAChEBI
Para-aminobenzoic acidChEBI
4-Aminobenzoic acidKegg
p-AminobenzoateKegg
RVPaba lipstickKegg
4-Amino-benzoateGenerator
g-AminobenzoateGenerator
g-Aminobenzoic acidGenerator
gamma-AminobenzoateGenerator
Γ-aminobenzoateGenerator
Γ-aminobenzoic acidGenerator
Para-aminobenzoateGenerator
4-AminobenzoateGenerator
acido P-AminobenzoicoHMDB
Acidum paraminobenzoicumHMDB
ActipolHMDB
AmbenHMDB
AminobenzoateHMDB
Aminobenzoic acidHMDB, MeSH
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
HacheminaHMDB, MeSH
Kyselina P-aminobenzoovaHMDB
P-amino-BenzoateHMDB
P-amino-Benzoic acidHMDB
PABHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
ParaminolHMDB, MeSH
ParanateHMDB
PotabaHMDB, MeSH
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
4 Aminobenzoic acidMeSH, HMDB
4 Aminobenzoic acid, potassium saltMeSH, HMDB
EpitelplastMeSH, HMDB
Jumer brand OF aminobenzoic acidMeSH, HMDB
Medea brand OF aminobenzoic acidMeSH, HMDB
ParaminanMeSH, HMDB
4-Aminobenzoate, potassiumMeSH, HMDB
Epit vitMeSH, HMDB
Llorens brand OF aminobenzoic acidMeSH, HMDB
PabasanMeSH, HMDB
Potassium aminobenzoateMeSH, HMDB
4-Aminobenzoic acid, potassium saltMeSH, HMDB
Aminobenzoate, potassiumMeSH, HMDB
Glenwood brand OF potassium aminobezoateMeSH, HMDB
Llorens brand OF aminobenzoic acid sodium saltMeSH, HMDB
Magnesium para-aminobenzoateMeSH, HMDB
Potassium 4 aminobenzoateMeSH, HMDB
Potassium 4-aminobenzoateMeSH, HMDB
P Aminobenzoic acidMeSH, HMDB
Para aminobenzoic acidMeSH, HMDB
Para-aminobenzoate, magnesiumMeSH, HMDB
p-Aminobenzoic acidChEBI
Chemical FormulaC7H7NO2
Average Molecular Mass137.136 g/mol
Monoisotopic Mass137.048 g/mol
CAS Registry Number150-13-0
IUPAC Name4-aminobenzoic acid
Traditional Namesunbrella
SMILESNC1=CC=C(C=C1)C(O)=O
InChI IdentifierInChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyALYNCZNDIQEVRV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.41 g/LALOGPS
logP0.78ALOGPS
logP0.8ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)2.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB02362
HMDB IDHMDB0001392
FooDB IDFDB001037
Phenol Explorer IDNot Available
KNApSAcK IDC00001401
BiGG IDNot Available
BioCyc IDP-AMINO-BENZOATE
METLIN ID3261
PDB IDNot Available
Wikipedia Link4-Aminobenzoic_acid
Chemspider ID953
ChEBI ID30753
PubChem Compound ID978
Kegg Compound IDC00568
YMDB IDYMDB00493
ECMDB IDECMDB01392
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12039592
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14745019
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15115392
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1527790
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16290145
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17149871
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17743450
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17800214
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19469519
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22767283
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22994574
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23063996
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23084339
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23144588
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23471007
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=3599019
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3820215
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=3950915
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=8411009
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=9406595
21. Sato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp.
22. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.
23. Sato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp.
24. Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60.
25. Laufer D, Cleghorn G, Forstner G, Ellis L, Koren G, Durie P: The bentiromide test using plasma p-aminobenzoic acid for diagnosing pancreatic insufficiency in young children. The effect of two different doses and a liquid meal. Gastroenterology. 1991 Jul;101(1):207-13.
26. Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51.
27. Lankisch PG, Brauneis J, Otto J, Goke B: Pancreolauryl and NBT-PABA tests. Are serum tests more practicable alternatives to urine tests in the diagnosis of exocrine pancreatic insufficiency? Gastroenterology. 1986 Feb;90(2):350-4.
28. Szewczuk A, Wellman-Bednawska M: The use of gamma-glutamyl-p-aminobenzoic acid as the substrate for determination of gamma-glutamyltranspeptidase activity in blood serum. Clin Chim Acta. 1978 Mar 1;84(1-2):19-26.
29. Kiss Z, Wolfling J, Csati S, Nagy F, Lonovics J, Schneider G: [The ursodeoxycholic acid-p-aminobenzoic acid test in the diagnosis of small bowel bacterial overgrowth syndrome]. Orv Hetil. 1997 May 18;138(20):1255-8.
30. Szewczuk A, Wellman-Bednawska M: Acyl derivatives of p-aminobenzoic acid as new substrates for the assay of serum acylase activity. Clin Chim Acta. 1978 Mar 1;84(1-2):27-31.
31. Derewlany LO, Knie B, Koren G: Human placental transfer and metabolism of p-aminobenzoic acid. J Pharmacol Exp Ther. 1994 May;269(2):761-5.
32. Ito S, Maruta K, Imai Y, Kato T, Ito M, Nakajima S, Fujita K, Kurahashi T: Urinary p-aminobenzoic acid determined in the pancreatic function test by liquid chromatography, with electrochemical detection. Clin Chem. 1982 Feb;28(2):323-6.
33. Durie PR, Yung-Jato LY, Soldin SJ, Verjee Z, Ellis L: Bentiromide test using liquid-chromatographic measurement of p-aminobenzoic acid and its metabolites for diagnosing pancreatic insufficiency in childhood. J Pediatr. 1992 Sep;121(3):413-6.