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Identification
Name4-Aminobenzoic Acid
Accession NumberDB02362  (EXPT02486)
TypeSmall Molecule
GroupsExperimental
Description

A member of the vitamin B complex. It used to be common in sunscreening agents until found to also be a sensitizer. The potassium salt is used therapeutically in fibrotic skin disorders. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
PabagelOwen
PabalateRobins
PabanolElder
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIITL2TJE8QTX
CAS number150-13-0
WeightAverage: 137.136
Monoisotopic: 137.047678473
Chemical FormulaC7H7NO2
InChI KeyInChIKey=ALYNCZNDIQEVRV-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
IUPAC Name
4-aminobenzoic acid
SMILES
NC1=CC=C(C=C1)C(O)=O
Taxonomy
DescriptionThis compound 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
  • Substituted aniline
  • Benzoyl
  • Aniline
  • Primary aromatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.957
Blood Brain Barrier+0.8436
Caco-2 permeable+0.7127
P-glycoprotein substrateNon-substrate0.8718
P-glycoprotein inhibitor INon-inhibitor0.9933
P-glycoprotein inhibitor IINon-inhibitor0.9847
Renal organic cation transporterNon-inhibitor0.9312
CYP450 2C9 substrateNon-substrate0.8483
CYP450 2D6 substrateNon-substrate0.9026
CYP450 3A4 substrateNon-substrate0.8251
CYP450 1A2 substrateNon-inhibitor0.87
CYP450 2C9 inhibitorNon-inhibitor0.9046
CYP450 2D6 inhibitorNon-inhibitor0.9844
CYP450 2C19 inhibitorNon-inhibitor0.9552
CYP450 3A4 inhibitorNon-inhibitor0.9397
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9841
Ames testNon AMES toxic0.9482
CarcinogenicityNon-carcinogens0.5373
BiodegradationReady biodegradable0.637
Rat acute toxicity1.3620 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9841
hERG inhibition (predictor II)Non-inhibitor0.9781
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point188.5 °CPhysProp
water solubility6110 mg/L (at 30 °C)YALKOWSKY,SH & HE,Y (2003)
logP0.83HANSCH,C ET AL. (1995)
logS-0.4ADME Research, USCD
pKa2.38 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility4.41 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-5zq0000000-b22b04854c131470802aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-8z20000000-dec9b6851633ff2c426cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-8xz0000000-b299bfaaed61286c2ff6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-iz00000000-ab0d2860a4f23e4fcad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z500000000-667a53f89529678400c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z200000000-0bbc34587525655f98efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-1z00000000-8f6c193895f5adf391beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z900000000-78f63538a3011f036551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-521edb7d484c452d0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-7ae0035594587960bab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-z000000000-35088605171b150e8b08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-ez00000000-d67f9d252f758529a83cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-7z00000000-e4d34d9516fe889137f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-nz00000000-387d1a3c2d588c6f8552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-z900000000-9ef61d003f891b00406fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-z100000000-eaf693e5f0cde39a548eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-sz00000000-225973eab49386396fa9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-yz00000000-bface88b2e77a7dce6e1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Si-Joon Lee, Hee-Young Jung, “Alpha-tocopherol 4-aminobenzoic acid ester compounds and method for preparing the same.” U.S. Patent US6222051, issued January, 1986.

US6222051
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. p-hydroxybenzoate hydroxylase

Kind: Protein

Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)

Pharmacological action: unknown

Components

Name UniProt ID Details
p-hydroxybenzoate hydroxylase P20586 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. p-hydroxybenzoate hydroxylase

Kind: Protein

Organism: Pseudomonas fluorescens

Pharmacological action: unknown

Components

Name UniProt ID Details
p-hydroxybenzoate hydroxylase P00438 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 27, 2014 14:27