Identification
NameAminobenzoic 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
Synonyms
4-aminobenzoic acid
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PabagelOwen
PabalateRobins
PabanolElder
Brand mixtures
NameLabellerIngredients
Neutral C + Coenzyme Q10 Plus Vitamins & MineralsNew Vision Nutritionals Company
Presun 15 LotionWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Categories
UNIITL2TJE8QTX
CAS number150-13-0
WeightAverage: 137.136
Monoisotopic: 137.047678473
Chemical FormulaC7H7NO2
InChI KeyALYNCZNDIQEVRV-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
p-hydroxybenzoate hydroxylaseProteinunknownNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)P20586 details
p-hydroxybenzoate hydroxylaseProteinunknownNot AvailablePseudomonas fluorescensP00438 details
Related Articles
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 CodesD02BA01 — Aminobenzoic acid
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
CapsuleOral
LotionTopical
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00yl-1960000000-b22b04854c131470802aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fkc-2900000000-dec9b6851633ff2c426cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yl-2890000000-b299bfaaed61286c2ff6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0079-9600000000-075c262f1e5d23ef097dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00yl-1960000000-4d7d9e3e3a7a741c72caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ku-4900000000-ab0d2860a4f23e4fcad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00mo-9100000000-667a53f89529678400c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-0bbc34587525655f98efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-8f6c193895f5adf391beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-78f63538a3011f036551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-521edb7d484c452d0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7ae0035594587960bab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-35088605171b150e8b08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-3900000000-d67f9d252f758529a83cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-e4d34d9516fe889137f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-6900000000-387d1a3c2d588c6f8552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r6-9200000000-9ef61d003f891b00406fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-eaf693e5f0cde39a548eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-7900000000-225973eab49386396fa9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000l-9600000000-ef69fcedbeb369c649bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00r6-9200000000-44f89c955a931e23991aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00dr-8900000000-bface88b2e77a7dce6e1View in MoNA
1D NMR1H NMR SpectrumNot Available
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
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 ParentsBenzoic acids / Benzoyl derivatives / Aniline and substituted anilines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides
SubstituentsAminobenzoic acid / Benzoic acid / Benzoyl / Aniline or substituted anilines / Amino acid or derivatives / Amino acid / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Amine
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsaminobenzoic 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
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
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 July 18, 2017 17:08