ECMDB: p-Aminobenzoic acid (ECMDB01392) (M2MDB000367)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (636)

Record Information

Version

2.0

Creation Date

2012-05-31 13:51:31 -0600

Update Date

2015-09-13 12:56:11 -0600

Secondary Accession Numbers

ECMDB01392

Identification

Name:

p-Aminobenzoic acid

Description

4-Aminobenzoic acid, para-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. PABA is an intermediate in the bacterial synthesis of folate. E. coli generate PABA from chorismate in a complex, multistep reaction. Note that sulfonamide drugs are structurally similar to PABA, and their antibacterial activity is due to their ability to interfere with the conversion of PABA to folate by the enzyme dihydropteroate synthetase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-Amino-4-carboxybenzene
4-Aminobenzoate
4-Aminobenzoic acid
4-Carboxyaniline
4-Carboxyphenylamine
p-aminobenzoate
ABEE
Acido p-aminobenzoico
Acidum paraminobenzoicum
Actipol
Amben
Aminobenzoate
Aminobenzoic acid
Aniline-4-carboxylate
Aniline-4-carboxylic acid
Anti-Chromotrichia factor
Anticanitic vitamin
Anticantic vitamin
Antichromotrichia factor
Bacterial vitamin H1
Chromotrichia factor
g-Aminobenzoate
g-Aminobenzoic acid
Gamma-Aminobenzoate
Gamma-Aminobenzoic acid
Hachemina
Kyselina p-aminobenzoova
P-Amino-Benzoate
P-Amino-Benzoic acid
P-Aminobenzoate
P-Aminobenzoic acid
P-Carboxyaniline
P-Carboxyphenylamine
PAB
PABA
Pabacyd
Pabafilm
Pabagel
Pabamine
Pabanol
Papacidum
Para-aminobenzoate
Para-Aminobenzoic acid
Paraminol
Paranate
Paranic acid
Potaba
Romavit
Rvpaba
RVPaba Lipstick
Sunbrella
Super Shade by Coppertone
Trichochromogenic factor
Trochromogenic factor
Vitamin BX
Vitamin H'
γ-Aminobenzoate
γ-Aminobenzoic acid

Chemical Formula:

C₇H₇NO₂

Weight:

Average: 137.136
Monoisotopic: 137.047678473

InChI Key:

ALYNCZNDIQEVRV-UHFFFAOYSA-N

InChI:

InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)

CAS number:

150-13-0

IUPAC Name:

4-aminobenzoic acid

Traditional IUPAC Name:

sunbrella

SMILES:

NC1=CC=C(C=C1)C(O)=O

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobenzoic acid (CHEBI:30753 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

188.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	6.11 mg/mL [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP:	0.83 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.41 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.8	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	2.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	13.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid
p-Aminobenzoic acid + 6-Hydroxymethyl-dihydropterin pyrophosphate > 7,8-Dihydropteroic acid + Pyrophosphate
6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <> 7,8-Dihydropteroic acid + Water
2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate <> Pyrophosphate + 7,8-Dihydropteroic acid
4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acid
Water + p-Aminobenzoyl glutamate > p-Aminobenzoic acid + L-Glutamate
2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid
4-Amino-4-deoxychorismate > p-Aminobenzoic acid + Pyruvic acid
6-Hydroxymethyl-dihydropterin pyrophosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid
4-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acid
4 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid
6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water
6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water

SMPDB Pathways:

Folate biosynthesis

PW000908

KEGG Pathways:

1,4-Dichlorobenzene degradation ec00627
Folate biosynthesis ec00790
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

p-aminobenzoate biosynthesis PWY-6543
tetrahydrofolate biosynthesis PWY-6614

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00yl-1960000000-b22b04854c131470802a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0fkc-2900000000-dec9b6851633ff2c426c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00yl-2890000000-b299bfaaed61286c2ff6	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-9600000000-075c262f1e5d23ef097d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00yl-1960000000-b22b04854c131470802a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fkc-2900000000-dec9b6851633ff2c426c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00yl-2890000000-b299bfaaed61286c2ff6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00yl-1960000000-4d7d9e3e3a7a741c72ca	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-5900000000-8244277f60fc465369b8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4900000000-299c72af4aa4008292bc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ku-4900000000-ab0d2860a4f23e4fcad4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00mo-9100000000-667a53f89529678400c7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-0bbc34587525655f98ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-8f6c193895f5adf391be	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9200000000-78f63538a3011f036551	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-521edb7d484c452d0da3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-7ae0035594587960bab7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9000000000-35088605171b150e8b08	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-3900000000-d67f9d252f758529a83c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-e4d34d9516fe889137f6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-6900000000-387d1a3c2d588c6f8552	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00r6-9200000000-9ef61d003f891b00406f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-eaf693e5f0cde39a548e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-7900000000-225973eab49386396fa9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-8f6c193895f5adf391be	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9200000000-78f63538a3011f036551	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-521edb7d484c452d0da3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7ae0035594587960bab7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9000000000-35088605171b150e8b08	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-173f144fba431cca9164	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-ab3524c5aadc6fdc28cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-67cea679b40b94c39ac0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-682d5d9d22372ece770b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9600000000-8d4bba3f647000005bb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5d9b80bb0601c2f238c2	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-8900000000-bface88b2e77a7dce6e1	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

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
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
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
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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
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
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
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
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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)

Links

External Links:

Resource	Link
CHEBI ID	30753
HMDB ID	HMDB01392
Pubchem Compound ID	978
Kegg ID	C00568
ChemSpider ID	953
Wikipedia	p-Aminobenzoic acid
BioCyc ID	P-AMINO-BENZOATE
EcoCyc ID	P-AMINO-BENZOATE
Ligand Expo	PAB

Enzymes

Protein Details

1. Dihydropteroate synthase

General function:: Involved in dihydropteroate synthase activity
Specific function:: DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide
Gene Name:: folP
Uniprot ID:: P0AC13
Molecular weight:: 30615

Reactions

(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate = diphosphate + dihydropteroate.

Protein Details

2. Aminodeoxychorismate lyase

General function:: Involved in 4-amino-4-deoxychorismate lyase activity
Specific function:: Converts 4-amino-4-deoxychorismate into 4-aminobenzoate (PABA) and pyruvate
Gene Name:: pabC
Uniprot ID:: P28305
Molecular weight:: 29715

Reactions

4-amino-4-deoxychorismate = 4-aminobenzoate + pyruvate.

p-Aminobenzoic acid (ECMDB01392) (M2MDB000367)

Structure for #<Compound:0x8708f0d4>

Enzymes

Reactions

Reactions