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4-Aminobenzoic acid (YMDB00493)

Identification
YMDB IDYMDB00493
Name4-Aminobenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Aminobenzoic acid (p-aminobenzoate) is a precursor in the tetrahydrofolate biosynthesis pathway; it is synthetised from chorismate. Tetrahydrofolate (vitamin B9) is the parent structure of the large family of folates coenzymes. Folates are essential cofactors that facilitate the transfer of one-carbon units from donor molecules into important biosynthetic pathways leading to methionine, purine, and pyrimidine biosynthesis. [Biocyc PWY-6543 and PWY-6614]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Amino-4-carboxybenzene
  • 4-Amino-benzoic acid
  • 4-Aminobenzoate
  • 4-Aminobenzoesaeure
  • 4-Aminobenzoic acid
  • 4-aminobenzoic acid, ion(1-)
  • 4-Carboxyaniline
  • 4-Carboxyphenylamine
  • ABEE
  • acido p-aminobenzoico
  • acidum paraminobenzoicum
  • Actipol
  • Amben
  • Aminobenzoate
  • Aminobenzoic acid
  • Aminobenzoic acid, para
  • Aniline-4-carboxylate
  • Aniline-4-carboxylic acid
  • Anti-Chromotrichia factor
  • Anticanitic vitamin
  • Anticantic vitamin
  • Antichromotrichia factor
  • Bacterial vitamin H1
  • Benzoic acid, 4-amino-
  • Benzoic acid, p-amino-
  • Chromotrichia factor
  • gamma-Aminobenzoate
  • gamma-Aminobenzoic acid
  • Hachemina
  • Kyselina p-aminobenzoova
  • p-amino-Benzoate
  • p-amino-Benzoic acid
  • p-Aminobenzoate
  • p-Aminobenzoesaeure
  • p-Aminobenzoic acid
  • p-Carboxyaniline
  • p-Carboxyphenylamine
  • PAB
  • PABA
  • Pabacyd
  • Pabafilm
  • Pabagel
  • Pabamine
  • Pabanol
  • Papacidum
  • para-aminobenzoate
  • para-Aminobenzoic acid
  • Paraminol
  • Paranate
  • Potaba
  • Romavit
  • Rvpaba
  • RVPaba Lipstick
  • Sunbrella
  • Super Shade by Coppertone
  • Trichochromogenic factor
  • Trochromogenic factor
  • Vitamin BX
  • Vitamin H'
  • 4-Amino-benzoate
  • g-Aminobenzoate
  • g-Aminobenzoic acid
  • Γ-aminobenzoate
  • Γ-aminobenzoic acid
  • 4 Aminobenzoic acid
  • 4 Aminobenzoic acid, potassium salt
  • Epitelplast
  • Jumer brand OF aminobenzoic acid
  • Medea brand OF aminobenzoic acid
  • Paraminan
  • 4-Aminobenzoate, potassium
  • Epit vit
  • Llorens brand OF aminobenzoic acid
  • Pabasan
  • Potassium aminobenzoate
  • 4-Aminobenzoic acid, potassium salt
  • Aminobenzoate, potassium
  • Glenwood brand OF potassium aminobezoate
  • Llorens brand OF aminobenzoic acid sodium salt
  • Magnesium para-aminobenzoate
  • Potassium 4 aminobenzoate
  • Potassium 4-aminobenzoate
  • P Aminobenzoic acid
  • Para aminobenzoic acid
  • Para-aminobenzoate, magnesium
CAS number150-13-0
WeightAverage: 137.136
Monoisotopic: 137.047678473
InChI KeyALYNCZNDIQEVRV-UHFFFAOYSA-N
InChIInChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
IUPAC Name4-aminobenzoic acid
Traditional IUPAC Namesunbrella
Chemical FormulaC7H7NO2
SMILESNC1=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.
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
Charge0
Melting point188.5 °C
Experimental Properties
PropertyValueReference
Water Solubility6.11 mg/mL at 30 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP0.83 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.41 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Extracellular, Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB Reactions
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-Aminobenzoic acid → Pyrophosphate + 7,8-Dihydropteroic acid
4-amino-4-deoxychorismate → 4-Aminobenzoic acid + hydron + Pyruvic acid
KEGG Reactions
4-amino-4-deoxychorismic acid → Pyruvic acid + hydron + 4-Aminobenzoic acid
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + 4-Aminobenzoic acid → water + 7,8-Dihydropteroic acid
(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + 4-Aminobenzoic acid → Pyrophosphate + 7,8-Dihydropteroic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00yl-1960000000-b22b04854c131470802aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fkc-2900000000-dec9b6851633ff2c426cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yl-2890000000-b299bfaaed61286c2ff6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-9600000000-075c262f1e5d23ef097dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00yl-1960000000-b22b04854c131470802aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fkc-2900000000-dec9b6851633ff2c426cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yl-2890000000-b299bfaaed61286c2ff6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00yl-1960000000-4d7d9e3e3a7a741c72caJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-5900000000-8244277f60fc465369b8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-4900000000-299c72af4aa4008292bcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ku-4900000000-ab0d2860a4f23e4fcad4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00mo-9100000000-667a53f89529678400c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-0bbc34587525655f98efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-8f6c193895f5adf391beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-78f63538a3011f036551JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-521edb7d484c452d0da3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7ae0035594587960bab7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-35088605171b150e8b08JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-3900000000-d67f9d252f758529a83cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-e4d34d9516fe889137f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-6900000000-387d1a3c2d588c6f8552JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r6-9200000000-9ef61d003f891b00406fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-eaf693e5f0cde39a548eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-7900000000-225973eab49386396fa9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-8f6c193895f5adf391beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-78f63538a3011f036551JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-521edb7d484c452d0da3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7ae0035594587960bab7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-35088605171b150e8b08JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-173f144fba431cca9164JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-ab3524c5aadc6fdc28cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-67cea679b40b94c39ac0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-682d5d9d22372ece770bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-8d4bba3f647000005bb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5d9b80bb0601c2f238c2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00dr-8900000000-bface88b2e77a7dce6e1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Sato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp.
External Links:
ResourceLink
CHEBI ID30753
HMDB IDHMDB01392
Pubchem Compound ID978
Kegg IDC00568
ChemSpider ID953
FOODB IDFDB001037
Wikipedia4-Aminobenzoic_acid
BioCyc IDP-AMINO-BENZOATE

Enzymes

Protein Details
1. Folic acid synthesis protein FOL1
General function:
Involved in dihydropteroate synthase activity
Specific function:
Catalyzes three sequential steps of tetrahydrofolate biosynthesis
Gene Name:
FOL1
Uniprot ID:
P53848
Molecular weight:
93119.10156
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine → 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine → AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate → diphosphate + dihydropteroate.
Protein Details
2. Aminodeoxychorismate lyase
General function:
Involved in catalytic activity
Specific function:
Converts 4-amino-4-deoxychorismate into 4-aminobenzoate (PABA) and pyruvate
Gene Name:
ABZ2
Uniprot ID:
Q03266
Molecular weight:
42639.39844
Reactions
4-amino-4-deoxychorismate → 4-aminobenzoate + pyruvate.