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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
SaltsNot Available
Brand names
NameCompany
PabagelOwen
PabalateRobins
PabanolElder
Brand mixturesNot Available
CategoriesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentAminobenzoic Acid Derivatives
Alternative parentsBenzoic Acids; Benzoyl Derivatives; Anilines; Primary Aromatic Amines; Enolates; Polyamines; Carboxylic Acids
Substituentsbenzoyl; aniline; primary aromatic amine; carboxylic acid derivative; enolate; polyamine; carboxylic acid; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminobenzoic acid derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.957
Blood Brain Barrier + 0.8436
Caco-2 permeable + 0.7127
P-glycoprotein substrate Non-substrate 0.8718
P-glycoprotein inhibitor I Non-inhibitor 0.9933
P-glycoprotein inhibitor II Non-inhibitor 0.9847
Renal organic cation transporter Non-inhibitor 0.9312
CYP450 2C9 substrate Non-substrate 0.8483
CYP450 2D6 substrate Non-substrate 0.9026
CYP450 3A4 substrate Non-substrate 0.8251
CYP450 1A2 substrate Non-inhibitor 0.87
CYP450 2C9 substrate Non-inhibitor 0.9046
CYP450 2D6 substrate Non-inhibitor 0.9844
CYP450 2C19 substrate Non-inhibitor 0.9552
CYP450 3A4 substrate Non-inhibitor 0.9397
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9841
Ames test Non AMES toxic 0.9482
Carcinogenicity Non-carcinogens 0.5373
Biodegradation Ready biodegradable 0.637
Rat acute toxicity 1.3620 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9841
hERG inhibition (predictor II) Non-inhibitor 0.9781
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 solubility4.41e+00 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 area63.32ChemAxon
rotatable bond count1ChemAxon
refractivity38.01ChemAxon
polarizability13.44ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02456
KEGG CompoundC00568
PubChem Compound978
PubChem Substance46504695
ChemSpider953
ChEBI30753
ChEMBL
HETPAB
Drug Product Database123803
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