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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:31 UTC
HMDB IDHMDB01392
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Aminobenzoic acid
Descriptionp-Aminobenzoic acid or 4-Aminobenzoic acid, or simply PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid. PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. PABA is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria. Certain bacteria in the human intestinal tract such as E. coli generate PABA from chorismate. Humans lack the enzymes to convert PABA to folate, and therefore require folate from dietary sources such as green leafy vegetables. Although some intestinal bacteria can synthesize folate from PABA and some E. coli can synthesize folate this requires six enzymatic activities in folate synthesis which are not all done in the same bacteria. PABA used to be a common sunscreening agent until found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders.
Structure
Thumb
Synonyms
ValueSource
P-Aminobenzoic acidKegg
RVPaba lipstickKegg
ABEEKegg
4-Aminobenzoic acidKegg
P-AminobenzoateKegg
AminobenzoateGenerator
4-AminobenzoateGenerator
1-amino-4-CarboxybenzeneHMDB
4-CarboxyanilineHMDB
4-CarboxyphenylamineHMDB
acido P-AminobenzoicoHMDB
Acidum paraminobenzoicumHMDB
ActipolHMDB
AmbenHMDB
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
gamma-AminobenzoateHMDB
gamma-Aminobenzoic acidHMDB
HacheminaHMDB
Kyselina P-aminobenzoovaHMDB
P-amino-BenzoateHMDB
P-amino-Benzoic acidHMDB
P-CarboxyanilineHMDB
P-CarboxyphenylamineHMDB
PABHMDB
PABAHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
Para-aminobenzoateHMDB
Para-aminobenzoic acidHMDB
ParaminolHMDB
ParanateHMDB
PotabaHMDB
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
Chemical FormulaC7H7NO2
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name4-aminobenzoic acid
Traditional Namesunbrella
CAS Registry Number150-13-0
SMILES
NC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyInChIKey=ALYNCZNDIQEVRV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Substituted aniline
  • Benzoyl
  • Aniline
  • Primary aromatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point188.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.11 mg/mLNot Available
LogP0.83HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility4.41 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00yl-1960000000-b22b04854c131470802aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fkc-2900000000-dec9b6851633ff2c426cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yl-2890000000-b299bfaaed61286c2ff6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ku-4900000000-ab0d2860a4f23e4fcad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00mo-9100000000-667a53f89529678400c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-0bbc34587525655f98efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-8f6c193895f5adf391beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-78f63538a3011f036551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-521edb7d484c452d0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7ae0035594587960bab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-35088605171b150e8b08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-3900000000-d67f9d252f758529a83cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-e4d34d9516fe889137f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-6900000000-387d1a3c2d588c6f8552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r6-9200000000-9ef61d003f891b00406fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-eaf693e5f0cde39a548eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-7900000000-225973eab49386396fa9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00dr-8900000000-bface88b2e77a7dce6e1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Liver
  • Placenta
  • Prostate
  • Skin
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified15.0 (5.01-32.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.36 (0.15-0.63) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02362
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001037
KNApSAcK IDC00001401
Chemspider ID953
KEGG Compound IDC00568
BioCyc IDP-AMINO-BENZOATE
BiGG IDNot Available
Wikipedia Linkp-Aminobenzoic acid
NuGOwiki LinkHMDB01392
Metagene LinkHMDB01392
METLIN ID3261
PubChem Compound978
PDB IDPAB
ChEBI ID30753
References
Synthesis ReferenceSato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60. [8182542 ]
  2. 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. [2044909 ]
  3. 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. [2293213 ]
  4. 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. [3484456 ]
  5. 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. [25149 ]
  6. 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. [9244859 ]
  7. 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. [305833 ]
  8. 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. [8182543 ]
  9. 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. [6976857 ]
  10. 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. [1517919 ]