Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-09-03 04:14:53 UTC |
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NP-MRD ID | NP0001240 |
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Natural Product DOI | https://doi.org/10.57994/0074 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | p-Aminobenzoic acid |
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Description | P-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). |
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Structure | InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10) |
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Synonyms | Value | Source |
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1-Amino-4-carboxybenzene | ChEBI | 4-Amino-benzoic acid | ChEBI | 4-Aminobenzoesaeure | ChEBI | 4-Carboxyaniline | ChEBI | 4-Carboxyphenylamine | ChEBI | ABEE | ChEBI | gamma-Aminobenzoic acid | ChEBI | p-Aminobenzoesaeure | ChEBI | p-Carboxyaniline | ChEBI | p-Carboxyphenylamine | ChEBI | PABA | ChEBI | Para-aminobenzoic acid | ChEBI | 4-Aminobenzoic acid | Kegg | p-Aminobenzoate | Kegg | RVPaba lipstick | Kegg | 4-Amino-benzoate | Generator | g-Aminobenzoate | Generator | g-Aminobenzoic acid | Generator | gamma-Aminobenzoate | Generator | Γ-aminobenzoate | Generator | Γ-aminobenzoic acid | Generator | Para-aminobenzoate | Generator | 4-Aminobenzoate | Generator | Acido p-aminobenzoico | HMDB | Acidum paraminobenzoicum | HMDB | Actipol | HMDB | Amben | HMDB | Aminobenzoate | HMDB | Aminobenzoic acid | HMDB | Aniline-4-carboxylate | HMDB | Aniline-4-carboxylic acid | HMDB | Anti-chromotrichia factor | HMDB | Anticanitic vitamin | HMDB | Anticantic vitamin | HMDB | Antichromotrichia factor | HMDB | Bacterial vitamin H1 | HMDB | Chromotrichia factor | HMDB | Hachemina | HMDB | Kyselina p-aminobenzoova | HMDB | p-Amino-benzoate | HMDB | p-Amino-benzoic acid | HMDB | PAB | HMDB | Pabacyd | HMDB | Pabafilm | HMDB | Pabagel | HMDB | Pabamine | HMDB | Pabanol | HMDB | Papacidum | HMDB | Paraminol | HMDB | Paranate | HMDB | Potaba | HMDB | Romavit | HMDB | Rvpaba | HMDB | Sunbrella | HMDB | Super shade by coppertone | HMDB | Trichochromogenic factor | HMDB | Trochromogenic factor | HMDB | Vitamin BX | HMDB | Vitamin h' | HMDB | 4 Aminobenzoic acid | HMDB | 4 Aminobenzoic acid, potassium salt | HMDB | Epitelplast | HMDB | Jumer brand OF aminobenzoic acid | HMDB | Medea brand OF aminobenzoic acid | HMDB | Paraminan | HMDB | 4-Aminobenzoate, potassium | HMDB | Epit vit | HMDB | Llorens brand OF aminobenzoic acid | HMDB | Pabasan | HMDB | Potassium aminobenzoate | HMDB | 4-Aminobenzoic acid, potassium salt | HMDB | Aminobenzoate, potassium | HMDB | Glenwood brand OF potassium aminobezoate | HMDB | Llorens brand OF aminobenzoic acid sodium salt | HMDB | Magnesium para-aminobenzoate | HMDB | Potassium 4 aminobenzoate | HMDB | Potassium 4-aminobenzoate | HMDB | p Aminobenzoic acid | HMDB | Para aminobenzoic acid | HMDB | Para-aminobenzoate, magnesium | HMDB | p-Aminobenzoic acid | ChEBI |
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Chemical Formula | C7H7NO2 |
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Average Mass | 137.1360 Da |
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Monoisotopic Mass | 137.04768 Da |
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IUPAC Name | 4-aminobenzoic acid |
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Traditional Name | sunbrella |
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CAS Registry Number | 150-13-0 |
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SMILES | NC1=CC=C(C=C1)C(O)=O |
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InChI Identifier | InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10) |
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InChI Key | ALYNCZNDIQEVRV-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | ravishankar@niist.res.in | Not Available | Not Available | 2024-05-12 | View Spectrum | HMBC NMR | [1H, 15N] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | ravishankar@niist.res.in | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | ravishankar@niist.res.in | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | ravishankar@niist.res.in | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental) | ravishankar@niist.res.in | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Aminobenzoic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 188.5 °C | Not Available | Boiling Point | 339.00 to 340.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | Water Solubility | 6.11 mg/mL | Not Available | LogP | 0.83 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Drissya T, Induja DK, Poornima MS, Jesmina ARS, Prabha B, Saumini M, Suresh CH, Raghu KG, Kumar BSD, Lankalapalli RS: A novel aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain. J Antibiot (Tokyo). 2022 Sep;75(9):491-497. doi: 10.1038/s41429-022-00547-1. Epub 2022 Aug 4. [PubMed:35922482 ]
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