3-hydroxyaspartic acid
aspartic acid, 3-hydroxy-
 
Notes:
None found
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CAS Number: 1860-87-3Picture of molecule3D/inchi
Nikkaji Web: J2.364.886E
XlogP3-AA: -4.40 (est)
Molecular Weight: 149.10279000
Formula: C4 H7 N O5
BioActivity Summary: listing
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 368.00 to  369.00 °C. @ 760.00 mm Hg (est)
Flash Point: 350.00 °F. TCC ( 176.80 °C. ) (est)
logP (o/w): -1.122 (est)
Soluble in:
 water, 2.22e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 3-hydroxyaspartic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 3-hydroxyaspartic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5425
National Institute of Allergy and Infectious Diseases: Data
 2-amino-3-hydroxybutanedioic acid
Chemidplus: 0001860873
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References:
 2-amino-3-hydroxybutanedioic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5425
Pubchem (sid): 135056538
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
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CHEMBL: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 arthrinium phaeospermum
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 dactylosporangium aurantiacum
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 pentaclethra macrophylla seed
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Synonyms:
2-amino-3-hydroxybutanedioic acid
3-aminomalic acid
beta-hydroxyaspartic acid
 aspartic acid, 3-hydroxy-
threo-2-amino-3-hydroxysuccinic acid
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Articles:
PubMed: Isolation and structures of pipecolidepsins A and B, cytotoxic cyclic depsipeptides from the Madagascan sponge Homophymia lamellosa.
PubMed: An acute glutamate exposure induces long-term down regulation of GLAST/EAAT1 uptake activity in cultured Bergmann glia cells.
PubMed: The SLC1 high-affinity glutamate and neutral amino acid transporter family.
PubMed: Astrocytes release D-serine by a large vesicle.
PubMed: Antinociceptive effect of rat D-serine racemase inhibitors, L-serine-O-sulfate, and L-erythro-3-hydroxyaspartate in an arthritic pain model.
PubMed: A practical synthesis of N α-Fmoc protected L-threo-β-hydroxyaspartic acid derivatives for coupling via α- or β-carboxylic group.
PubMed: Neuroprotective effect of CPDT on THA-induced cortical motor neuron death in an organotypic culture model.
PubMed: Insights into the mechanism of Pseudomonas dacunhae aspartate beta-decarboxylase from rapid-scanning stopped-flow kinetics.
PubMed: Neuroprotective effect of erythropoietin in amyotrophic lateral sclerosis (ALS) model in vitro. Ultrastructural study.
PubMed: Characterization of chronic glutamate-mediated motor neuron toxicity in organotypic spinal cord culture prepared from ALS model mice.
PubMed: Neuroprotective effects of yokukansan, a traditional Japanese medicine, on glutamate-mediated excitotoxicity in cultured cells.
PubMed: Iron is a potential key mediator of glutamate excitotoxicity in spinal cord motor neurons.
PubMed: gamma-Glutamate and beta-hydroxyaspartate in proteins.
PubMed: Glutamate transporters of blood platelets as potential peripheral markers to analyze changes of glutamate transport activity in brain under altered gravity conditions.
PubMed: Huperzine A provides neuroprotection against several cell death inducers using in vitro model systems of motor neuron cell death.
PubMed: Non-heme hydroxylase engineering for simple enzymatic synthesis of L-threo-hydroxyaspartic acid.
PubMed: Genome-scale analysis of anti-metabolite directed strain engineering.
PubMed: A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid.
PubMed: Tryptophan breakdown pathway in bipolar mania.
PubMed: [Modulating effect of glutamate transporter inhibitors on accumulation and release of the neuromediator by the brain nerve terminals in rats].
PubMed: Autophagic degeneration of motor neurons in a model of slow glutamate excitotoxicity in vitro.
PubMed: Effects of the inhibitors on glutamate uptake by nerve terminals after exposure of rats to centrifuge-induced hypergravity.
PubMed: Expression of GFP-tagged neuronal glutamate transporters in cerebellar Purkinje neurons.
PubMed: Structure, conformation and biological activity of a novel lipodepsipeptide from Pseudomonas corrugata: cormycin A.
PubMed: Protective cap over CA1 synapses: extrasynaptic glutamate does not reach the postsynaptic density.
PubMed: Activation of protein kinase C reduces GLAST in the plasma membrane of rat Müller cells in primary culture.
PubMed: Identification of glutamate transporters and receptors in mouse testis.
PubMed: Glutamate spillover in the striatum depresses dopaminergic transmission by activating group I metabotropic glutamate receptors.
PubMed: Serine racemase homologue of Saccharomyces cerevisiae has L-threo-3-hydroxyaspartate dehydratase activity.
PubMed: A novel enzyme, D-3-hydroxyaspartate aldolase from Paracoccus denitrificans IFO 13301: purification, characterization, and gene cloning.
PubMed: Electrical and pharmacological properties of the slow depolarization induced by Schaffer collateral stimulation in astrocytes of the rat hippocampal CA1 region.
PubMed: Metabotropic glutamate receptor-mediated hetero-synaptic interaction of red- and green-cone inputs to LHC of carp retina.
PubMed: Isoflurane preconditioning reduces purkinje cell death in an in vitro model of rat cerebellar ischemia.
PubMed: Neuronal glutamate uptake Contributes to GABA synthesis and inhibitory synaptic strength.
PubMed: The glutamate transporters EAAT2 and EAAT3 mediate cysteine uptake in cortical neuron cultures.
PubMed: Modulation of glutamatergic transmission by bergmann glial cells in rat cerebellum in situ.
PubMed: Involvement of acetylated tubulin in the regulation of Na+,K+ -ATPase activity in cultured astrocytes.
PubMed: Local application of L- threo-hydroxyaspartate and malonate in rats in vivo induces rigidity and damages neurons of the substantia nigra, pars compacta.
PubMed: Glutamate-induced calcium increase in myotubes depends on up-regulation of a sodium-dependent transporter.
PubMed: Feeding-induced decrease in extracellular glutamate level in the rat nucleus accumbens: dependence on glutamate uptake.
PubMed: Beta-amyloid enhances glial glutamate uptake activity and attenuates synaptic efficacy.
PubMed: Inhibitor of glutamate transport alters synaptic transmission at sensorimotor synapses in Aplysia.
PubMed: gamma-glutamate and beta-hydroxyaspartate in proteins.
PubMed: Differing effects of substrate and non-substrate transport inhibitors on glutamate uptake reversal.
PubMed: Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5).
PubMed: Hypoglycemia induces general neuronal death, whereas hypoxia and glutamate transport blockade lead to selective retinal ganglion cell death in vitro.
PubMed: Methylmercury inhibits cysteine uptake in cultured primary astrocytes, but not in neurons.
PubMed: Kinetics and activation of postsynaptic kainate receptors at thalamocortical synapses: role of glutamate clearance.
PubMed: Dopamine-dependent inhibition of glycine release in the nucleus accumbens of the rat brain during food consumption.
PubMed: A Na+-dependent electrogenic glutamate transporter current in voltage-clamped cells of corpora allata in the cricket Gryllus bimaculatus.
PubMed: Methylmercury-mediated inhibition of 3H-D-aspartate transport in cultured astrocytes is reversed by the antioxidant catalase.
PubMed: Release of D,L-threo-beta-hydroxyaspartate as a false transmitter from excitatory amino acid-releasing nerve terminals.
PubMed: Regulation of mitochondrial glutamine/glutamate metabolism by glutamate transport: studies with (15)N.
PubMed: Effects of glial glutamate transporter inhibitors on intracellular Na+ in mouse astrocytes.
PubMed: Possible linkage between glutamate transporter and mitogen-activated protein kinase cascade in cultured rat cortical astrocytes.
PubMed: Transient increase in the high affinity [3H]-L-glutamate uptake activity during in vitro development of hippocampal neurons in culture.
PubMed: Müller cell protection of rat retinal ganglion cells from glutamate and nitric oxide neurotoxicity.
PubMed: 3-Nitropropionic acid neurotoxicity in organotypic striatal and corticostriatal slice cultures is dependent on glucose and glutamate.
PubMed: Effect of ionotropic glutamate receptors antagonists on the modifications in extracellular glutamate and aspartate levels during picrotoxin seizures: a microdialysis study in freely moving rats.
PubMed: [Dopamine-dependent inhibition of glycine release in the rat nucleus accumbens during feeding].
PubMed: Synaptically released glutamate does not overwhelm transporters on hippocampal astrocytes during high-frequency stimulation.
PubMed: Na+-dependent high-affinity glutamate transport in macrophages.
PubMed: [Changes in glutamate release in the rat nucleus accumbens during food and pain reinforcement].
PubMed: Glutamate transport blockade has a differential effect on AMPA and NMDA receptor-mediated synaptic transmission in the developing barrel cortex.
PubMed: Control of synaptic depression by glutamate transporters.
PubMed: Transient treatments with L-glutamate and threo-beta-hydroxyaspartate induce swelling of rat cultured astrocytes.
PubMed: Metabotropic glutamate receptors and blockade of glial Krebs cycle depress glycinergic synaptic currents of mouse hypoglossal motoneurons.
PubMed: SNARE protein-dependent glutamate release from astrocytes.
PubMed: Trans-inhibition of glutamate transport prevents excitatory amino acid-induced glycolysis in astrocytes.
PubMed: Biosynthetic origin of syringomycin and syringopeptin 22, toxic secondary metabolites of the phytopathogenic bacterium Pseudomonas syringae pv. syringae.
PubMed: Effects of inhibiting glutamine synthetase and blocking glutamate uptake on b-wave generation in the isolated rat retina.
PubMed: Motor neuron degeneration is attenuated in bax-deficient neurons in vitro.
PubMed: Characterization of (2S,2'R,3'R)-2-(2',3'-[3H]-dicarboxycyclopropyl)glycine binding in rat brain.
PubMed: Action of excitatory amino acids on hypodermis and the motornervous system of Ascaris suum: pharmacological evidence for a glutamate transporter.
PubMed: DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters.
PubMed: Modulation of human glutamate transporter activity by phorbol ester.
PubMed: AMPA receptor-mediated slow neuronal death in the rat spinal cord induced by long-term blockade of glutamate transporters with THA.
PubMed: Postsynaptic glutamate transport at the climbing fiber-Purkinje cell synapse.
PubMed: Intracerebral microdialysis study of glutamate reuptake in awake, behaving rats.
PubMed: Glutamatergic enteric neurons.
PubMed: Transporters buffer synaptically released glutamate on a submillisecond time scale.
PubMed: Stimulated release of lactate in freely moving rats is dependent on the uptake of glutamate.
PubMed: Short-lived intermediates in aspartate aminotransferase systems.
PubMed: Inhibition of glutamate uptake causes an acute increase in aqueous humor protein.
PubMed: Aspartate aminotransferase complexed with erythro-beta-hydroxyaspartate: crystallographic and spectroscopic identification of the carbinolamine intermediate.
PubMed: Attenuation of trimethyltin-evoked glutamate (GLU) efflux from rat cortical and hippocampal slices.
PubMed: Glutamate transport modulation of paracellular permeability across LLC-PK1-F+ monolayers.
PubMed: The mechanisms controlling physiologically stimulated changes in rat brain glucose and lactate: a microdialysis study.
PubMed: Autoradiographic studies indicate regional variations in the characteristics of L-glutamate transporters in the rat brain.
PubMed: Modulation of excitatory synaptic transmission by low concentrations of glutamate in cultured rat hippocampal neurons.
PubMed: Inhibition of glutamate uptake induces progressive accumulation of extracellular glutamate and neuronal damage in rat cortical cultures.
PubMed: Characterization of recombinant human coagulation factor XFriuli.
PubMed: Noise analysis of the glutamate-activated current in photoreceptors.
PubMed: Cone photoreceptors respond to their own glutamate release in the tiger salamander.
PubMed: The glutamate uptake regulatory protein (Grp) of Zymomonas mobilis and its relation to the global regulator Lrp of Escherichia coli.
PubMed: Reaction of aspartate aminotransferase with L-erythro-3-hydroxyaspartate: involvement of Tyr70 in stabilization of the catalytic intermediates.
PubMed: Microdialysis as a tool for in vivo investigation of glutamate transport capacity in rat brain.
PubMed: Effects of a glutamate uptake inhibitor on glutamate release induced by veratridine and ischemia.
PubMed: Other lipopeptides.
PubMed: Effects of L-trans-pyrrolidine-2,4-dicarboxylate and L-threo-3-hydroxyaspartate on the binding of [3H]L-aspartate, [3H]alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA), [3H]DL-(E)-2-amino-4-propyl-5-phosphono-3-pentenoate (CGP 39653), [3H]6-cyano-7-nitroquinoxaline-2,3-dione (CNQX) and [3H]kainate studied by autoradiography in rat forebrain.
PubMed: L-glutamate uptake inhibitors may stimulate phosphoinositide hydrolysis in baby hamster kidney cells expressing mGluR1a via heteroexchange with L-glutamate without direct activation of mGluR1a.
PubMed: Block of glutamate transporters potentiates postsynaptic excitation.
PubMed: Regional differences in the inhibition of L-glutamate and L-aspartate sodium-dependent high affinity uptake systems in rat CNS synaptosomes by L-trans-pyrrolidine-2,4-dicarboxylate, threo-3-hydroxy-D-aspartate and D-aspartate.
PubMed: Pre- and post-synaptic modulators of excitatory neurotransmission: comparative effects on hypoxia/hypoglycemia in cortical cultures.
PubMed: Glial contributions to excitatory neurotransmission in cultured hippocampal cells.
PubMed: Na(+)-dependent high affinity uptake of L-glutamate in primary cultures of human fibroblasts isolated from three different types of tissue.
PubMed: The Na(+)-dependent binding of [3H]L-aspartate in thaw-mounted sections of rat forebrain.
PubMed: Glucose can fuel glutamate uptake in ischemic brain.
PubMed: Depolarization elicits, while hyperpolarization blocks uptake of endogenous glutamate by retinal horizontal cells of the turtle.
PubMed: (2S,3S,4R)-2-(carboxycyclopropyl)glycine, a potent and competitive inhibitor of both glial and neuronal uptake of glutamate.
PubMed: Chronic inhibition of glutamate uptake produces a model of slow neurotoxicity.
PubMed: Modulatory action of kainic acid on glutamate release from rat brain cortical synaptosomes.
PubMed: Binding of protein S to C4b-binding protein. Mutagenesis of protein S.
PubMed: Evidence for the existence of O-linked sugar chains consisting of glucose and xylose in bovine thrombospondin.
PubMed: Philanthotoxins block glutamatergic transmission in rat hippocampus--I. Reduction of high affinity glutamate uptake demonstrated by light microscopy surface autoradiography.
PubMed: The pharmacological profile of glutamate-evoked ascorbic acid efflux measured by in vivo electrochemistry.
PubMed: beta-Hydroxyaspartic acid and beta-hydroxyasparagine residues in recombinant human protein S are not required for anticoagulant cofactor activity or for binding to C4b-binding protein.
PubMed: Structure-function relationships of epidermal growth factor modules in vitamin K-dependent clotting factors.
PubMed: Prepeptide sequence of cinnamycin (Ro 09-0198): the first structural gene of a duramycin-type lantibiotic.
PubMed: Electrogenic uptake of glutamate and aspartate into glial cells isolated from the salamander (Ambystoma) retina.
PubMed: DL-threo-3-hydroxyaspartate reduces NMDA receptor activation by glutamate in cultured neurons.
PubMed: Characterization of glutamate uptake systems in astrocyte primary cultures from rat brain.
PubMed: Anatomical and pharmacological heterogeneity of D-[3H]aspartate binding sites.
PubMed: Excitatory amino acid pathways in brain-stimulation reward.
PubMed: Calcium binding to the isolated beta-hydroxyaspartic acid-containing epidermal growth factor-like domain of bovine factor X.
PubMed: The neurotoxicity of 1-methyl-4-phenylpyridinium in cultured cerebellar granule cells.
PubMed: Substitution of a lysyl residue for arginine 386 of Escherichia coli aspartate aminotransferase.
PubMed: Hydroxylation of aspartic acid in domains homologous to the epidermal growth factor precursor is catalyzed by a 2-oxoglutarate-dependent dioxygenase.
PubMed: Beta-hydroxyaspartic acid in the first epidermal growth factor-like domain of protein C. Its role in Ca2+ binding and biological activity.
PubMed: The role of beta-hydroxyaspartate and adjacent carboxylate residues in the first EGF domain of human factor IX.
PubMed: Potentiation by kainate of excitatory amino acid release in striatum: complementary in vivo and in vitro experiments.
PubMed: beta-Hydroxyaspartic acid or beta-hydroxyasparagine in bovine low density lipoprotein receptor and in bovine thrombomodulin.
PubMed: Occurrence of beta-hydroxylated asparagine residues in non-vitamin K-dependent proteins containing epidermal growth factor-like domains.
PubMed: Continuous glutamate leakage from brain cells is balanced by compensatory high-affinity reuptake transport.
PubMed: Na+-dependent "binding" of D-aspartate in brain membranes is largely due to uptake into membrane-bounded saccules.
PubMed: Binding of iron by factor IX. Possible role for beta-hydroxyaspartic acid.
PubMed: Protein C in bovine plasma after warfarin treatment. Purification, partial characterization, and beta-hydroxyaspartic acid content.
PubMed: Calcium binding to a human factor IXa derivative lacking gamma-carboxyglutamic acid: evidence for two high-affinity sites that do not involve beta-hydroxyaspartic acid.
PubMed: Inhibitors of high-affinity uptake augment depolarizations of hippocampal neurons induced by glutamate, kainate and related compounds.
PubMed: Neurotoxicity of L-glutamate and DL-threo-3-hydroxyaspartate in the rat striatum.
PubMed: Interaction of aspartate and aspartate-derived antimetabolites with the enzymes of the threonine biosynthetic pathway of Escherichia coli.
PubMed: Structure and function of protein C.
PubMed: Beta-hydroxyaspartic acid in vitamin K-dependent plasma proteins from scorbutic and warfarin-treated guinea pigs.
PubMed: erythro-beta-Hydroxyaspartic acid in bovine factor IX and factor X.
PubMed: Beta-hydroxyaspartic acid in vitamin K-dependent proteins.
PubMed: The occurrence of beta-hydroxyaspartic acid in the vitamin K-dependent blood coagulation zymogens.
PubMed: Complete amino acid sequence of the light chain of human blood coagulation factor X: evidence for identification of residue 63 as beta-hydroxyaspartic acid.
PubMed: Effects of anoxia on the stimulated release of amino acid neurotransmitters in the cerebellum in vitro.
PubMed: Potentiation of L-glutamate and L-aspartate excitation of cat spinal neurones by the stereoisomers of threo-3-hydroxyaspartate.
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