2-AMINO-5-PHOSPHONOVALERATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C5H12NO5P
Molecular Weight	197.1262
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-AMINO-5-PHOSPHONOVALERATE

Structure Search

SMILES

NC(CCCP(O)(O)=O)C(O)=O

InChI

InChIKey=VOROEQBFPPIACJ-UHFFFAOYSA-N

InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C5H12NO5P
Molecular Weight	197.1262
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2145436	Inhibitor 8504		290.0 nM [IC50]

PubMed

Title	Date	PubMed
Effect of lactate on the synaptic potential, energy metabolism, calcium homeostasis and extracellular glutamate concentration in the dentate gyrus of the hippocampus from guinea-pig.	2001	11377841
Modification of extracellular matrix by enzymatic removal of chondroitin sulfate and by lack of tenascin-R differentially affects several forms of synaptic plasticity in the hippocampus.	2001	11377840
PKC activation rescues LTP from NMDA receptor blockade.	2001	11345123
Differential mechanisms of Ca2+ responses in glial cells evoked by exogenous and endogenous glutamate in rat hippocampus.	2001	11345120
Slow inhibitory potentials in the teleost Mauthner cell.	2001	11246169
An electrophysiological study of neural pathways for corticofugally inhibited neurons in the central nucleus of the inferior colliculus of the big brown bat, Eptesicus fuscus.	2001 Apr	11355376
A transient inhibition of mitochondrial ATP synthesis by nitric oxide synthase activation triggered apoptosis in primary cortical neurons.	2001 Apr	11299330
Pharmacological characterization of threo-3-methylglutamic acid with excitatory amino acid transporters in native and recombinant systems.	2001 Apr	11299317
Novelty enhances retrieval: molecular mechanisms involved in rat hippocampus.	2001 Apr	11298809
NMDA-evoked calcium transients and currents in the suprachiasmatic nucleus: gating by the circadian system.	2001 Apr	11298803
Spontaneous GABAergic postsynaptic currents in Cajal-Retzius cells in neonatal rat cerebral cortex.	2001 Apr	11298799
Kindling induces transient fast inhibition in the dentate gyrus--CA3 projection.	2001 Apr	11298797
Theta-frequency facilitation of AMPA receptor-mediated synaptic currents in the principal cells of the medial septum.	2001 Apr	11287493
Peripheral group I metabotropic glutamate receptors modulate nociception in mice.	2001 Apr	11276233
Dissociation between synaptic depression and block of long-term depression induced by raising the temperature in rat hippocampal slices.	2001 Apr	11170219
Intracellular calcium reduces light-induced excitatory post-synaptic responses in salamander retinal ganglion cells.	2001 Apr 1	11283224
In vitro eye-blink classical conditioning is NMDA receptor dependent and involves redistribution of AMPA receptor subunit GluR4.	2001 Apr 1	11264317
Firing properties of identified superior laryngeal neurons in the nucleus ambiguus in the rat.	2001 Apr 27	11297809
Ontogeny of ionotropic glutamate receptor expression in human fetal brain.	2001 Apr 30	11334999
Inorganic iron complexes derived from the nitric oxide donor nitroprusside: competitive N-methyl-D-aspartate receptor antagonists with nanomolar affinity.	2001 Feb 1	11172739
Dopamine-independent locomotion following blockade of N-methyl-D-aspartate receptors in the ventral tegmental area.	2001 Jul	11408546
Increased spinal N-methyl-D-aspartate receptor function after 20 h of carrageenan-induced inflammation.	2001 Jul	11406334
Spreading depression in human neocortical slices.	2001 Jul 6	11430863
Effect of neonatal capsaicin treatment on neural activity in the medullary dorsal horn of neonatal rats evoked by electrical stimulation to the trigeminal afferents: an optical, electrophysiological, and quantitative study.	2001 Jul 6	11430856
Early onset of glutamatergic and GABAergic synaptic activity in the visual layers of the rodent superior colliculus.	2001 Jun	11337194
Amygdalar nmda receptors are critical for the expression of multiple conditioned fear responses.	2001 Jun 1	11356900
Injections of the NMDA receptor antagonist aminophosphonopentanoic acid into the lateral nucleus of the amygdala block the expression of fear-potentiated startle and freezing.	2001 Jun 1	11356899
NMDA-mediated activation of the medial amygdala initiates a downstream neuroendocrine memory responsible for pseudopregnancy in the female rat.	2001 Jun 1	11356898
Gabaergic inhibition antagonizes adaptive adjustment of the owl's auditory space map during the initial phase of plasticity.	2001 Jun 15	11404421
N-Methyl-D-aspartate-induced c-Fos expression is enhanced in the forebrain structures related to emotion in Fyn-deficient mice.	2001 Jun 29	11423094
MAP2 phosphorylation and visual plasticity in Xenopus.	2001 Jun 29	11423088
The role of N-methyl-D-aspartate receptors in synaptic plasticity of rat visual cortex in vitro: effect of sensory experience.	2001 Jun 29	11406317
Unipolar brush cells form a glutamatergic projection system within the mouse cerebellar cortex.	2001 Jun 4	11331532
Dopamine, but not glutamate, receptor blockade in the basolateral amygdala attenuates conditioned reward in a rat model of relapse to cocaine-seeking behavior.	2001 Mar	11351937
Synergistic analgesic effects of intrathecal midazolam and NMDA or AMPA receptor antagonists in rats.	2001 Mar	11305832
Regulatory role of nitric oxide over hippocampal 5-HT release in vivo.	2001 Mar	11284445
The analgesic interaction between intrathecal clonidine and glutamate receptor antagonists on thermal and formalin-induced pain in rats.	2001 Mar	11226109
Role of nitric oxide on pressor mechanisms within the dorsomedial and rostral ventrolateral medulla in anaesthetized cats.	2001 Mar	11207669
Contribution of postsynaptic Ca2+ to the induction of post-tetanic potentiation in the neural circuit for siphon withdrawal in Aplysia.	2001 Mar 1	11222663
NMDA and AMPA antagonist infusions into the ventral striatum impair different steps of spatial information processing in a nonassociative task in mice.	2001 Mar 15	11245698
The effect of N-acetyl-L-aspartic acid dilithium salt on dopamine release and synthesis in the rat striatum in vivo.	2001 Mar 23	11282114
Quinolinic acid induces oxidative stress in rat brain synaptosomes.	2001 Mar 26	11277599
Regulation of spontaneous inhibitory synaptic transmission by endogenous glutamate via non-NMDA receptors in cultured rat hippocampal neurons.	2001 May	11369028
Postsynaptic modulation of AMPA receptor-mediated synaptic responses and LTP by the type 3 ryanodine receptor.	2001 May	11358488
Kindling induces transient NMDA receptor-mediated facilitation of high-frequency input in the rat dentate gyrus.	2001 May	11353034
Post-episode depression of GABAergic transmission in spinal neurons of the chick embryo.	2001 May	11353031
Short-term plasticity at inhibitory synapses in rat striatum and its effects on striatal output.	2001 May	11353025
Enhanced temporal stability of cholinergic hippocampal gamma oscillations following respiratory alkalosis in vitro.	2001 May	11353022
Melanin concentrating hormone depresses synaptic activity of glutamate and GABA neurons from rat lateral hypothalamus.	2001 May 15	11351031
Characterization of spontaneous excitatory synaptic currents in pyramidal cells of rat prelimbic cortex.	2001 May 18	11368981

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:48 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:48 GMT 2025`
Record UNII	39PJ29YY8Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AP-5 (±)-

Preferred Name

English

2-AMINO-5-PHOSPHONOVALERATE

Systematic Name

English

AP 5 (AMINO ACID)

Common Name

English

AP 5 (±)-

Common Name

English

2-APV

Common Name

English

NORVALINE, 5-PHOSPHONO- (±)-

Systematic Name

English

(±)-AMINO-5-PHOSPHONOPENTANOIC ACID

Systematic Name

English

DL-2-AMINO-5-PHOSPHONOVALERIC ACID

Common Name

English

DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID

Common Name

English

5-PHOSPHONO-DL-NORVALINE

Systematic Name

English

DL-AP-5

Code

English

APV (±)-

Common Name

English

DL-NORVALINE, 5-PHOSPHONO-

Systematic Name

English

(±)-2-AMINO-5-PHOSPHONOVALERIC ACID

Systematic Name

English

2-AMINO-5-PHOSPHONOVALERIC ACID

Systematic Name

English

2-AMINO-5-PHOSPHONOPENTANOIC ACID

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

NMDA receptor antagonist