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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:13 UTC
NP-MRD IDNP0001240
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Aminobenzoic acid
DescriptionP-Aminobenzoic acid, also known as 4-aminobenzoic acid or 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 into 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 sunscreen agent until it was found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders. PABA can also be found in Acetobacter (DOI: 10.3181/00379727-52-14147).
Structure
Thumb
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
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
HacheminaHMDB
Kyselina p-aminobenzoovaHMDB
p-Amino-benzoateHMDB
p-Amino-benzoic acidHMDB
PABHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
ParaminolHMDB
ParanateHMDB
PotabaHMDB
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
4 Aminobenzoic acidHMDB
4 Aminobenzoic acid, potassium saltHMDB
EpitelplastHMDB
Jumer brand OF aminobenzoic acidHMDB
Medea brand OF aminobenzoic acidHMDB
ParaminanHMDB
4-Aminobenzoate, potassiumHMDB
Epit vitHMDB
Llorens brand OF aminobenzoic acidHMDB
PabasanHMDB
Potassium aminobenzoateHMDB
4-Aminobenzoic acid, potassium saltHMDB
Aminobenzoate, potassiumHMDB
Glenwood brand OF potassium aminobezoateHMDB
Llorens brand OF aminobenzoic acid sodium saltHMDB
Magnesium para-aminobenzoateHMDB
Potassium 4 aminobenzoateHMDB
Potassium 4-aminobenzoateHMDB
p Aminobenzoic acidHMDB
Para aminobenzoic acidHMDB
Para-aminobenzoate, magnesiumHMDB
p-Aminobenzoic acidChEBI
Chemical FormulaC7H7NO2
Average Mass137.1360 Da
Monoisotopic Mass137.04768 Da
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 KeyALYNCZNDIQEVRV-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point188.5 °CNot Available
Boiling Point339.00 to 340.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility6.11 mg/mLNot Available
LogP0.83Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility4.41 g/LALOGPS
logP10(0.78) g/LALOGPS
logP10(0.8) g/LChemAxon
logS10(-1.5) g/LALOGPS
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
HMDB IDHMDB0001392
DrugBank IDDB02362
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001037
KNApSAcK IDC00001401
Chemspider ID953
KEGG Compound IDC00568
BioCyc IDP-AMINO-BENZOATE
BiGG IDNot Available
Wikipedia Link4-Aminobenzoic_acid
METLIN ID3261
PubChem Compound978
PDB IDNot Available
ChEBI ID30753
Good Scents IDrw1198771
References
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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]