Aminobenzoic acid

Identification

Name
Aminobenzoic acid
Accession Number
DB02362  (EXPT02486)
Type
Small Molecule
Groups
Experimental
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
Synonyms
  • 4-aminobenzoic acid
International/Other Brands
Pabagel (Owen) / Pabalate (Robins) / Pabanol (Elder)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Neutral C + Coenzyme Q10 Plus Vitamins & MineralsAminobenzoic acid (15 mg) + Cyanocobalamin (150 mcg) + Folic Acid (0.5 mg) + Magnesium (50 mg) + Potassium (3 mg) + Pyridoxine hydrochloride (25 mg) + Sodium selenite (40 mcg) + Ubidecarenone (10 mg) + Calcium ascorbate (320 mg)CapsuleOralNew Vision Nutritionals Company1998-06-072002-11-20Canada
Presun 15 LotionAminobenzoic acid (5 %) + Oxybenzone (3 %) + Padimate O (5 %)LotionTopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1991-12-311997-08-11Canada
Categories
UNII
TL2TJE8QTX
CAS number
150-13-0
Weight
Average: 137.136
Monoisotopic: 137.047678473
Chemical Formula
C7H7NO2
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)
IUPAC Name
4-aminobenzoic acid
SMILES
NC1=CC=C(C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
Up-hydroxybenzoate hydroxylaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Up-hydroxybenzoate hydroxylaseNot AvailablePseudomonas fluorescens
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB01392
KEGG Drug
D02456
KEGG Compound
C00568
PubChem Compound
978
PubChem Substance
46504695
ChemSpider
953
BindingDB
50145829
ChEBI
30753
ChEMBL
CHEMBL542
HET
PAB
ATC Codes
D02BA01 — Aminobenzoic acid
PDB Entries
1ius / 1iut / 1iuu / 1pbd / 2dza / 3q2a / 3tyz

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral
LotionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)188.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00yl-1960000000-b22b04854c131470802a
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0fkc-2900000000-dec9b6851633ff2c426c
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00yl-2890000000-b299bfaaed61286c2ff6
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0079-9600000000-075c262f1e5d23ef097d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00yl-1960000000-b22b04854c131470802a
GC-MS Spectrum - GC-MSGC-MSsplash10-0fkc-2900000000-dec9b6851633ff2c426c
GC-MS Spectrum - GC-MSGC-MSsplash10-00yl-2890000000-b299bfaaed61286c2ff6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00yl-1960000000-4d7d9e3e3a7a741c72ca
Mass Spectrum (Electron Ionization)MSsplash10-00dr-8900000000-bface88b2e77a7dce6e1
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00ku-4900000000-ab0d2860a4f23e4fcad4
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00mo-9100000000-667a53f89529678400c7
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014i-9000000000-0bbc34587525655f98ef
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-0900000000-8f6c193895f5adf391be
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-9200000000-78f63538a3011f036551
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9000000000-521edb7d484c452d0da3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-7ae0035594587960bab7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00kf-9000000000-35088605171b150e8b08
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00di-3900000000-d67f9d252f758529a83c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-1900000000-e4d34d9516fe889137f6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-6900000000-387d1a3c2d588c6f8552
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00r6-9200000000-9ef61d003f891b00406f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-eaf693e5f0cde39a548e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-7900000000-225973eab49386396fa9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-8f6c193895f5adf391be
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9200000000-78f63538a3011f036551
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-521edb7d484c452d0da3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-7ae0035594587960bab7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9000000000-35088605171b150e8b08
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000l-9600000000-ef69fcedbeb369c649bc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-3900000000-d67f9d252f758529a83c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-1900000000-e4d34d9516fe889137f6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-6900000000-387d1a3c2d588c6f8552
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r6-9200000000-44f89c955a931e23991a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-eaf693e5f0cde39a548e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-7900000000-225973eab49386396fa9
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzoic acids
Alternative Parents
Benzoic acids / Benzoyl derivatives / Aniline and substituted anilines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides
show 1 more
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
show 9 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aminobenzoic acid (CHEBI:30753)

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Monooxygenase activity
Specific Function
Not Available
Gene Name
pobA
Uniprot ID
P20586
Uniprot Name
p-hydroxybenzoate hydroxylase
Molecular Weight
44323.175 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Fad binding
Specific Function
Not Available
Gene Name
pobA
Uniprot ID
P00438
Uniprot Name
p-hydroxybenzoate hydroxylase
Molecular Weight
44321.205 Da
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:17139284]
  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:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:13