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Human Metabolome Database Version 3.5

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Showing metabocard for p-Aminobenzoic acid (HMDB01392)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-17 14:03:42 -0600
HMDB ID HMDB01392
Secondary Accession Numbers None
Metabolite Identification
Common Name p-Aminobenzoic acid
Description p-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Amino-4-carboxybenzene
  2. 4-Aminobenzoate
  3. 4-Aminobenzoic acid
  4. 4-Carboxyaniline
  5. 4-Carboxyphenylamine
  6. ABEE
  7. Acido p-aminobenzoico
  8. Acidum paraminobenzoicum
  9. Actipol
  10. Amben
  11. Aminobenzoate
  12. Aminobenzoic acid
  13. Aniline-4-carboxylate
  14. Aniline-4-carboxylic acid
  15. Anti-Chromotrichia factor
  16. Anticanitic vitamin
  17. Anticantic vitamin
  18. Antichromotrichia factor
  19. Bacterial vitamin H1
  20. Chromotrichia factor
  21. gamma-Aminobenzoate
  22. gamma-Aminobenzoic acid
  23. Hachemina
  24. Kyselina p-aminobenzoova
  25. p-Amino-Benzoate
  26. p-Amino-Benzoic acid
  27. p-Aminobenzoate
  28. p-Aminobenzoic acid
  29. p-Carboxyaniline
  30. p-Carboxyphenylamine
  31. PAB
  32. PABA
  33. Pabacyd
  34. Pabafilm
  35. Pabagel
  36. Pabamine
  37. Pabanol
  38. Papacidum
  39. Para-aminobenzoate
  40. Para-Aminobenzoic acid
  41. Paraminol
  42. Paranate
  43. Potaba
  44. Romavit
  45. Rvpaba
  46. RVPaba Lipstick
  47. Sunbrella
  48. Super Shade by Coppertone
  49. Trichochromogenic factor
  50. Trochromogenic factor
  51. Vitamin BX
  52. Vitamin H'
Chemical Formula C7H7NO2
Average Molecular Weight 137.136
Monoisotopic Molecular Weight 137.047678473
IUPAC Name 4-aminobenzoic acid
Traditional IUPAC Name 4-aminobenzoic acid
CAS Registry Number 150-13-0
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 Key ALYNCZNDIQEVRV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Aminobenzoic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • aminobenzoic acid(ChEBI)
Substituents
  • Aniline
  • Benzoyl
  • Carboxylic Acid
Direct Parent Aminobenzoic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 188.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 6.11 mg/mL Not Available
LogP 0.83 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 4.41 g/L ALOGPS
LogP 0.78 ALOGPS
LogP 0.8 ChemAxon
LogS -1.49 ALOGPS
pKa (strongest acidic) 4.77 ChemAxon
pKa (strongest basic) 2.69 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 38.01 ChemAxon
Polarizability 13.44 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Placenta
  • Liver
  • Prostate
  • Skin
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
15.0 (5.01-32.0) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.11 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.36 (0.15-0.63) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02362 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001037
KNApSAcK ID C00001401 Link_out
Chemspider ID 953 Link_out
KEGG Compound ID C00568 Link_out
BioCyc ID P-AMINO-BENZOATE Link_out
BiGG ID Not Available
Wikipedia Link p-Aminobenzoic acid Link_out
NuGOwiki Link HMDB01392 Link_out
Metagene Link HMDB01392 Link_out
METLIN ID 3261 Link_out
PubChem Compound 978 Link_out
PDB ID PAB Link_out
ChEBI ID 30753 Link_out
References
Synthesis Reference Sato, 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. Pubmed: 8182542 Link_out
  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. Pubmed: 2044909 Link_out
  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. Pubmed: 2293213 Link_out
  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. Pubmed: 3484456 Link_out
  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. Pubmed: 25149 Link_out
  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. Pubmed: 9244859 Link_out
  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. Pubmed: 305833 Link_out
  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. Pubmed: 8182543 Link_out
  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. Pubmed: 6976857 Link_out
  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. Pubmed: 1517919 Link_out