Anthranilic acid

Identification

Name
Anthranilic acid
Accession Number
DB04166  (EXPT00283, EXPT00656, DB04056)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2-Aminobenzoesäure
  • 2-aminobenzoic acid
  • 2-carboxyaniline
  • o-Aminobenzoesäure
  • o-Aminobenzoic acid
  • o-carboxyaniline
  • Vitamin L1
External IDs
NCI-C01730 / NSC-144 / NSC-3937
Categories
UNII
0YS975XI6W
CAS number
118-92-3
Weight
Average: 137.136
Monoisotopic: 137.047678473
Chemical Formula
C7H7NO2
InChI Key
RWZYAGGXGHYGMB-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
IUPAC Name
2-aminobenzoic acid
SMILES
NC1=CC=CC=C1C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UL-amino-acid oxidaseNot AvailableHuman
UD-amino-acid oxidaseNot AvailableHuman
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
DrugInteractionDrug group
MefloquineThe therapeutic efficacy of Anthranilic acid can be decreased when used in combination with Mefloquine.Approved
MianserinThe therapeutic efficacy of Anthranilic acid can be decreased when used in combination with Mianserin.Approved, Investigational
OrlistatThe serum concentration of Anthranilic acid can be decreased when it is combined with Orlistat.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01123
KEGG Compound
C00108
PubChem Compound
227
PubChem Substance
46504575
ChemSpider
222
BindingDB
50376751
ChEBI
30754
ChEMBL
CHEMBL14173
PharmGKB
PA10247
HET
BE2
Wikipedia
Anthranilic_acid
PDB Entries
1an9 / 1c0i / 1e8n / 1f8s / 1zfp / 1zyk / 2e4a / 2gvq / 2hu8 / 2jb3
show 10 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.81 mg/mLALOGPS
logP0.78ALOGPS
logP1.45ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m3·mol-1ChemAxon
Polarizability13.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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) (2 TMS)GC-MSsplash10-014i-1950000000-5595652a2e8f93679437
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-1960000000-889ed538406d5aa57a5d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00xr-9650000000-e0611721f0bf7b5bb2f8
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-00r6-2910000000-0daf33fe6231b5e15b0e
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014i-3970000000-3351c7d8036c42c4cd41
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00kf-9400000000-b65ee27505e8c4bcca28
GC-MS Spectrum - EI-BGC-MSsplash10-014i-0490000000-4165d1d7b8fff53889dd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1950000000-5595652a2e8f93679437
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1960000000-889ed538406d5aa57a5d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xr-9650000000-e0611721f0bf7b5bb2f8
GC-MS Spectrum - GC-MSGC-MSsplash10-00r6-2910000000-0daf33fe6231b5e15b0e
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-3970000000-3351c7d8036c42c4cd41
Mass Spectrum (Electron Ionization)MSsplash10-014u-9600000000-5b8e271f29d04a87c89a
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-00kf-9400000000-395d42e11895b80f4e9c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-8c390367e035aea8527a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-899b596a227cd9a1769d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-3cc9be013399e30d7eae
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-655ef8fc722e0b1b6d14
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-4d0520217d12a10f9273
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-bab8539624c8af4e6434
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-f51f2db6bf1da2e26d20
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-86d698a8c81a3e765840
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-0900000000-6df94712ad580bebfd21
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-9100000000-a1ce64280c2d7f3b85df
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9000000000-454f848122c778e951ad
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-7de473c1ca6bf702b2ac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-94f19baa1ae36f43be60
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00di-2900000000-c2bbbe5e00434e635ad2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-4900000000-f8f84a5536375300afbd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-9000000000-91ceb340e5cf91473cba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-80972c552b97ae764bc4
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-4900000000-f494672ce9de4818b8c5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-9300000000-9bbb2f00817538e072d5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0900000000-e7e07e78dd5baa5c3f87
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-54a3d793d6fbf0220b47
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0umi-9200000000-bd780d6ca957af006488
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-9800000000-93111d593c96a3298a6c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-827a516778b53b67d6fe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-2ce4a55660af3b4001e8
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-6df94712ad580bebfd21
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9100000000-a1ce64280c2d7f3b85df
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-454f848122c778e951ad
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-83d46c8510058fb9f250
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-94f19baa1ae36f43be60
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-9300000000-9bbb2f00817538e072d5
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000f-9500000000-cfcef789bab8a6e7c0da
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-2900000000-c2bbbe5e00434e635ad2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-4900000000-f8f84a5536375300afbd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-91ceb340e5cf91473cba
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-80972c552b97ae764bc4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-899b596a227cd9a1769d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-3cc9be013399e30d7eae
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-655ef8fc722e0b1b6d14
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-0b31adf3d32eac74f278
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-f51f2db6bf1da2e26d20
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-86d698a8c81a3e765840
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-4900000000-f494672ce9de4818b8c5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-63c42bae0761c6677919
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-f96bcdb70bf400e8a185
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 / Vinylogous amides / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Primary amines / Organopnictogen compounds / Organooxygen compounds
show 2 more
Substituents
Aminobenzoic acid / Benzoic acid / Benzoyl / Aniline or substituted anilines / Vinylogous amide / Amino acid or derivatives / Amino acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aminobenzoic acid (CHEBI:30754)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-amino-acid oxidase activity
Specific Function
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name
IL4I1
Uniprot ID
Q96RQ9
Uniprot Name
L-amino-acid oxidase
Molecular Weight
62880.52 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids...
Gene Name
DAO
Uniprot ID
P14920
Uniprot Name
D-amino-acid oxidase
Molecular Weight
39473.75 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:38