5698-54-4,MFCD01014168
Catalog No.:AA019VHL

5698-54-4 | 4-[(carboxymethyl)amino]benzoic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
100mg
95%
2 weeks  
$201.00   $141.00
- +
250mg
95%
2 weeks  
$305.00   $214.00
- +
1g
95%
2 weeks  
$660.00   $462.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA019VHL
Chemical Name:
4-[(carboxymethyl)amino]benzoic acid
CAS Number:
5698-54-4
Molecular Formula:
C9H9NO4
Molecular Weight:
195.1721
MDL Number:
MFCD01014168
SMILES:
OC(=O)CNc1ccc(cc1)C(=O)O
NSC Number:
14973
Properties
Computed Properties
 
Complexity:
221  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
0.1  

Downstream Synthesis Route

[1]Dyeretal.[JournalofOrganicChemistry,1957,vol.22,p.78]

[1]Runti[IlFarmaco,scienzaetecnica,1950,vol.5,p.528,532,533]

[1]Runti[IlFarmaco,scienzaetecnica,1950,vol.5,p.528,532,533]

[2]Ainley;Robinson[JournaloftheChemicalSociety,1937,p.453,455]

542-85-8    5698-54-4   
4-(3-ethyl-4-oxo-2-thioxo-imidazolidin-1-yl)-benzoicacid 

[1]CurrentPatentAssignee:DUPONTDENEMOURSINC-US2551134,1947,A

[1]Takeda;Kuroda[YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1925,#515,p.4][ChemischesZentralblatt,1925,vol.96,#I,p.2304]

Literature

Title: Functional expression of system x(c)- is upregulated by asbestos but not crystalline silica in murine macrophages.

Journal: Inhalation toxicology 20120701

Title: Suppressive effect of preconditioning low-frequency stimulation on subsequent induction of long-term potentiation by high frequency stimulation in hippocampal CA3 neurons.

Journal: Brain research 20120417

Title: Hypoxic preconditioning involves system Xc- regulation in mouse neural stem cells.

Journal: Stem cell research 20120301

Title: Functional upregulation of system xc- by fibroblast growth factor-2.

Journal: Neuropharmacology 20120201

Title: The cystine/cysteine cycle and GSH are independent and crucial antioxidant systems in malignant melanoma cells and represent druggable targets.

Journal: Antioxidants & redox signaling 20111101

Title: Glutamatergic targets for enhancing extinction learning in drug addiction.

Journal: Current neuropharmacology 20101201

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Involvement of inositol-1,4,5-trisphosphate receptors in the bidirectional synaptic plasticity induced in hippocampal CA1 neurons by 1-10 Hz low-frequency stimulation.

Journal: Neuroscience 20100630

Title: Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x(c)(-) over the vesicular glutamate transporter.

Journal: Bioorganic & medicinal chemistry letters 20100415

Title: Pharmacogenomic approach reveals a role for the x(c)- cystine/glutamate antiporter in growth and celastrol resistance of glioma cell lines.

Journal: The Journal of pharmacology and experimental therapeutics 20100301

Title: Metabotropic glutamate receptors: potential drug targets for psychiatric disorders.

Journal: The open medicinal chemistry journal 20100101

Title: Sulfasalazine inhibits the growth of primary brain tumors independent of nuclear factor-kappaB.

Journal: Journal of neurochemistry 20090701

Title: mGluR(1) Receptors Contribute to Non-Purinergic Slow Excitatory Transmission to Submucosal VIP Neurons of Guinea-Pig Ileum.

Journal: Frontiers in neuroscience 20090101

Title: The potent non-competitive mGlu1 receptor antagonist BAY 36-7620 differentially affects synaptic plasticity in area cornu ammonis 1 of rat hippocampal slices and impairs acquisition in the water maze task in mice.

Journal: Neuroscience 20081119

Title: Characterization of the cystine/glutamate transporter in the outer plexiform layer of the vertebrate retina.

Journal: The European journal of neuroscience 20081001

Title: Blunted cystine-glutamate antiporter function in the nucleus accumbens promotes cocaine-induced drug seeking.

Journal: Neuroscience 20080813

Title: Contribution of cystine-glutamate antiporters to the psychotomimetic effects of phencyclidine.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20080601

Title: Face-washing behavior induced by the group I metabotropic glutamate receptor agonist (S)-3,5-DHPG in mice is mediated by mGlu1 receptor.

Journal: European journal of pharmacology 20080531

Title: Modulation by group 1 metabotropic glutamate receptors of depotentiation in the dentate gyrus of freely moving rats.

Journal: Hippocampus 20080101

Title: Cystine-glutamate transporter SLC7A11 mediates resistance to geldanamycin but not to 17-(allylamino)-17-demethoxygeldanamycin.

Journal: Molecular pharmacology 20071201

Title: Expression of a functional metabotropic glutamate receptor 5 on enteric glia is altered in states of inflammation.

Journal: Glia 20070601

Title: Involvement of hippocampal metabotropic glutamate receptors in radial maze performance.

Journal: Neuroreport 20070507

Title: Chemoinformatics analysis identifies cytotoxic compounds susceptible to chemoresistance mediated by glutathione and cystine/glutamate transport system xc-.

Journal: Journal of medicinal chemistry 20070419

Title: Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: 'staged' inhibitor design.

Journal: Journal of medicinal chemistry 20061214

Title: Vesicular and non-vesicular glutamate release in the nucleus accumbens in conditions of a forced change of behavioral strategy.

Journal: Neuroscience and behavioral physiology 20050901

Title: Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance.

Journal: Cancer research 20050815

Title: Inhibition of cystine uptake disrupts the growth of primary brain tumors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050803

Title: Regulation of extracellular glutamate in the prefrontal cortex: focus on the cystine glutamate exchanger and group I metabotropic glutamate receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20050701

Title: Glutamate antagonists attenuate the action of NC-1900, a vasopressin fragment analog, on passive avoidance task performance in mice.

Journal: Peptides 20050501

Title: Tonic release of glutamate by a DIDS-sensitive mechanism in rat hippocampal slices.

Journal: The Journal of physiology 20050415

Title: Reversal of hippocampal LTP by spontaneous seizure-like activity: role of group I mGluR and cell depolarization.

Journal: Journal of neurophysiology 20050101

Title: MGluRs regulate the expression of neuronal calcium sensor proteins NCS-1 and VILIP-1 and the immediate early gene arg3.1/arc in the hippocampus in vivo.

Journal: Biochemical and biophysical research communications 20040924

Title: Membrane topology of system xc- light subunit reveals a re-entrant loop with substrate-restricted accessibility.

Journal: The Journal of biological chemistry 20040723

Title: Differentiation of substrate and non-substrate inhibitors of transport system xc(-): an obligate exchanger of L-glutamate and L-cystine.

Journal: Neuropharmacology 20040201

Title: [Vesicular and nonvesicular glutamate release in the nucleus accumbens during a forced switch in behavioral strategy].

Journal: Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova 20040101

Title: Inhibition of non-vesicular glutamate release by group III metabotropic glutamate receptors in the nucleus accumbens.

Journal: Journal of neurochemistry 20031201

Title: Induction of long-term potentiation of C fibre-evoked spinal field potentials requires recruitment of group I, but not group II/III metabotropic glutamate receptors.

Journal: Pain 20031201

Title: In vitro characterization of [3H]MethoxyPyEP, an mGluR5 selective radioligand.

Journal: Life sciences 20030606

Title: Group I mGlu receptors regulate the expression of the neuronal calcium sensor protein VILIP-1 in vitro and in vivo: implications for mGlu receptor-dependent hippocampal plasticity?

Journal: Neuropharmacology 20030501

Title: High frequency stimulation-induced dendritic calcium waves in rat hippocampal neurons.

Journal: Neuroscience letters 20021225

Title: Activation of spinal metabotropic glutamate receptors elicits cardiovascular responses in pentobarbital anesthetized rats.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20021001

Title: Differential effects of mGluR1 and mGlur5 antagonism on spatial learning in rats.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry 20020718

Title: Group I metabotropic glutamate receptors (mGluRs) modulate visual responses in the superficial superior colliculus of the rat.

Journal: The Journal of physiology 20020615

Title: Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens.

Journal: The Journal of pharmacology and experimental therapeutics 20020101

Title: Activation of group I mGluRs is necessary for induction of long-term depression at striatal synapses.

Journal: Journal of neurophysiology 20011101

Title: The group I metabotropic glutamate receptor antagonist S-4-CPG modulates the locomotor response produced by the activation of D1-like, but not D2-like, dopamine receptors in the rat nucleus accumbens.

Journal: The European journal of neuroscience 20010601

Title: mGlu5 receptors and nociceptive function II. mGlu5 receptors functionally expressed on peripheral sensory neurones mediate inflammatory hyperalgesia.

Journal: Neuropharmacology 20010101

Title: NMDA receptor antagonists change behavioral activity of rats treated with (S)-4CPG.

Journal: Polish journal of pharmacology 20010101

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SDS
Tags:5698-54-4 Molecular Formula|5698-54-4 MDL|5698-54-4 SMILES|5698-54-4 4-[(carboxymethyl)amino]benzoic acid
Catalog No.: AA019VHL
5698-54-4,MFCD01014168
5698-54-4 | 4-[(carboxymethyl)amino]benzoic acid
Pack Size: 100mg
Purity: 95%
2 weeks
$201.00 $141.00
Pack Size: 250mg
Purity: 95%
2 weeks
$305.00 $214.00
Pack Size: 1g
Purity: 95%
2 weeks
$660.00 $462.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA019VHL
Chemical Name: 4-[(carboxymethyl)amino]benzoic acid
CAS Number: 5698-54-4
Molecular Formula: C9H9NO4
Molecular Weight: 195.1721
MDL Number: MFCD01014168
SMILES: OC(=O)CNc1ccc(cc1)C(=O)O
NSC Number: 14973
Properties
Complexity: 221  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 14  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 4  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 0.1  
Downstream Synthesis Route
123-91-1    75-44-5    5698-54-4    113926-34-4 

[1]Dyeretal.[JournalofOrganicChemistry,1957,vol.22,p.78]

64-17-5    5698-54-4    23284-85-7 

[1]Runti[IlFarmaco,scienzaetecnica,1950,vol.5,p.528,532,533]

64-17-5    5698-54-4    26815-64-5 

[1]Runti[IlFarmaco,scienzaetecnica,1950,vol.5,p.528,532,533]

[2]Ainley;Robinson[JournaloftheChemicalSociety,1937,p.453,455]

542-85-8    5698-54-4   
4-(3-ethyl-4-oxo-2-thioxo-imidazolidin-1-yl)-benzoicacid 

[1]CurrentPatentAssignee:DUPONTDENEMOURSINC-US2551134,1947,A

59081-60-6    5698-54-4 

[1]Takeda;Kuroda[YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1925,#515,p.4][ChemischesZentralblatt,1925,vol.96,#I,p.2304]

Literature fold

Title: Functional expression of system x(c)- is upregulated by asbestos but not crystalline silica in murine macrophages.

Journal: Inhalation toxicology20120701

Title: Suppressive effect of preconditioning low-frequency stimulation on subsequent induction of long-term potentiation by high frequency stimulation in hippocampal CA3 neurons.

Journal: Brain research20120417

Title: Hypoxic preconditioning involves system Xc- regulation in mouse neural stem cells.

Journal: Stem cell research20120301

Title: Functional upregulation of system xc- by fibroblast growth factor-2.

Journal: Neuropharmacology20120201

Title: The cystine/cysteine cycle and GSH are independent and crucial antioxidant systems in malignant melanoma cells and represent druggable targets.

Journal: Antioxidants & redox signaling20111101

Title: Glutamatergic targets for enhancing extinction learning in drug addiction.

Journal: Current neuropharmacology20101201

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters20101101

Title: Involvement of inositol-1,4,5-trisphosphate receptors in the bidirectional synaptic plasticity induced in hippocampal CA1 neurons by 1-10 Hz low-frequency stimulation.

Journal: Neuroscience20100630

Title: Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x(c)(-) over the vesicular glutamate transporter.

Journal: Bioorganic & medicinal chemistry letters20100415

Title: Pharmacogenomic approach reveals a role for the x(c)- cystine/glutamate antiporter in growth and celastrol resistance of glioma cell lines.

Journal: The Journal of pharmacology and experimental therapeutics20100301

Title: Metabotropic glutamate receptors: potential drug targets for psychiatric disorders.

Journal: The open medicinal chemistry journal20100101

Title: Sulfasalazine inhibits the growth of primary brain tumors independent of nuclear factor-kappaB.

Journal: Journal of neurochemistry20090701

Title: mGluR(1) Receptors Contribute to Non-Purinergic Slow Excitatory Transmission to Submucosal VIP Neurons of Guinea-Pig Ileum.

Journal: Frontiers in neuroscience20090101

Title: The potent non-competitive mGlu1 receptor antagonist BAY 36-7620 differentially affects synaptic plasticity in area cornu ammonis 1 of rat hippocampal slices and impairs acquisition in the water maze task in mice.

Journal: Neuroscience20081119

Title: Characterization of the cystine/glutamate transporter in the outer plexiform layer of the vertebrate retina.

Journal: The European journal of neuroscience20081001

Title: Blunted cystine-glutamate antiporter function in the nucleus accumbens promotes cocaine-induced drug seeking.

Journal: Neuroscience20080813

Title: Contribution of cystine-glutamate antiporters to the psychotomimetic effects of phencyclidine.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology20080601

Title: Face-washing behavior induced by the group I metabotropic glutamate receptor agonist (S)-3,5-DHPG in mice is mediated by mGlu1 receptor.

Journal: European journal of pharmacology20080531

Title: Modulation by group 1 metabotropic glutamate receptors of depotentiation in the dentate gyrus of freely moving rats.

Journal: Hippocampus20080101

Title: Cystine-glutamate transporter SLC7A11 mediates resistance to geldanamycin but not to 17-(allylamino)-17-demethoxygeldanamycin.

Journal: Molecular pharmacology20071201

Title: Expression of a functional metabotropic glutamate receptor 5 on enteric glia is altered in states of inflammation.

Journal: Glia20070601

Title: Involvement of hippocampal metabotropic glutamate receptors in radial maze performance.

Journal: Neuroreport20070507

Title: Chemoinformatics analysis identifies cytotoxic compounds susceptible to chemoresistance mediated by glutathione and cystine/glutamate transport system xc-.

Journal: Journal of medicinal chemistry20070419

Title: Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: 'staged' inhibitor design.

Journal: Journal of medicinal chemistry20061214

Title: Vesicular and non-vesicular glutamate release in the nucleus accumbens in conditions of a forced change of behavioral strategy.

Journal: Neuroscience and behavioral physiology20050901

Title: Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance.

Journal: Cancer research20050815

Title: Inhibition of cystine uptake disrupts the growth of primary brain tumors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20050803

Title: Regulation of extracellular glutamate in the prefrontal cortex: focus on the cystine glutamate exchanger and group I metabotropic glutamate receptors.

Journal: The Journal of pharmacology and experimental therapeutics20050701

Title: Glutamate antagonists attenuate the action of NC-1900, a vasopressin fragment analog, on passive avoidance task performance in mice.

Journal: Peptides20050501

Title: Tonic release of glutamate by a DIDS-sensitive mechanism in rat hippocampal slices.

Journal: The Journal of physiology20050415

Title: Reversal of hippocampal LTP by spontaneous seizure-like activity: role of group I mGluR and cell depolarization.

Journal: Journal of neurophysiology20050101

Title: MGluRs regulate the expression of neuronal calcium sensor proteins NCS-1 and VILIP-1 and the immediate early gene arg3.1/arc in the hippocampus in vivo.

Journal: Biochemical and biophysical research communications20040924

Title: Membrane topology of system xc- light subunit reveals a re-entrant loop with substrate-restricted accessibility.

Journal: The Journal of biological chemistry20040723

Title: Differentiation of substrate and non-substrate inhibitors of transport system xc(-): an obligate exchanger of L-glutamate and L-cystine.

Journal: Neuropharmacology20040201

Title: [Vesicular and nonvesicular glutamate release in the nucleus accumbens during a forced switch in behavioral strategy].

Journal: Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova20040101

Title: Inhibition of non-vesicular glutamate release by group III metabotropic glutamate receptors in the nucleus accumbens.

Journal: Journal of neurochemistry20031201

Title: Induction of long-term potentiation of C fibre-evoked spinal field potentials requires recruitment of group I, but not group II/III metabotropic glutamate receptors.

Journal: Pain20031201

Title: In vitro characterization of [3H]MethoxyPyEP, an mGluR5 selective radioligand.

Journal: Life sciences20030606

Title: Group I mGlu receptors regulate the expression of the neuronal calcium sensor protein VILIP-1 in vitro and in vivo: implications for mGlu receptor-dependent hippocampal plasticity?

Journal: Neuropharmacology20030501

Title: High frequency stimulation-induced dendritic calcium waves in rat hippocampal neurons.

Journal: Neuroscience letters20021225

Title: Activation of spinal metabotropic glutamate receptors elicits cardiovascular responses in pentobarbital anesthetized rats.

Journal: Naunyn-Schmiedeberg's archives of pharmacology20021001

Title: Differential effects of mGluR1 and mGlur5 antagonism on spatial learning in rats.

Journal: Pharmacology, biochemistry, and behavior20020901

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry20020718

Title: Group I metabotropic glutamate receptors (mGluRs) modulate visual responses in the superficial superior colliculus of the rat.

Journal: The Journal of physiology20020615

Title: Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens.

Journal: The Journal of pharmacology and experimental therapeutics20020101

Title: Activation of group I mGluRs is necessary for induction of long-term depression at striatal synapses.

Journal: Journal of neurophysiology20011101

Title: The group I metabotropic glutamate receptor antagonist S-4-CPG modulates the locomotor response produced by the activation of D1-like, but not D2-like, dopamine receptors in the rat nucleus accumbens.

Journal: The European journal of neuroscience20010601

Title: mGlu5 receptors and nociceptive function II. mGlu5 receptors functionally expressed on peripheral sensory neurones mediate inflammatory hyperalgesia.

Journal: Neuropharmacology20010101

Title: NMDA receptor antagonists change behavioral activity of rats treated with (S)-4CPG.

Journal: Polish journal of pharmacology20010101

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