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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

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

Targets

Primary TargetPharmacologyConditionPotency
290.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Bidirectional modulation of basal forebrain N-methyl-D-aspartate receptor function differentially affects visual attention but not visual discrimination performance.
2001
PKC activation rescues LTP from NMDA receptor blockade.
2001
Differential mechanisms of Ca2+ responses in glial cells evoked by exogenous and endogenous glutamate in rat hippocampus.
2001
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine.
2001
Muscarinic cholinergic and glutamatergic reciprocal regulation of expression of hippocampal cholinergic neurostimulating peptide precursor protein gene in rat hippocampus.
2001
Temperature-dependent separation of a delayed-onset long-lasting enhancement mediated by coactivation of NMDA and metabotropic glutamate receptors following a transient exposure of extracellular high Ca(2+).
2001
Allosteric modulation of [3H]-CGP39653 binding through the glycine site of the NMDA receptor: further studies in rat and human brain.
2001 Apr
Novelty enhances retrieval: molecular mechanisms involved in rat hippocampus.
2001 Apr
Kindling induces transient fast inhibition in the dentate gyrus--CA3 projection.
2001 Apr
Theta-frequency facilitation of AMPA receptor-mediated synaptic currents in the principal cells of the medial septum.
2001 Apr
Long-term enhancement of synaptic transmission induced by veratridine in rat CA3 hippocampal neurons.
2001 Apr
A-85380 and epibatidine each interact with disparate spinal nicotinic receptor subtypes to achieve analgesia and nociception.
2001 Apr
In vitro eye-blink classical conditioning is NMDA receptor dependent and involves redistribution of AMPA receptor subunit GluR4.
2001 Apr 1
Firing properties of identified superior laryngeal neurons in the nucleus ambiguus in the rat.
2001 Apr 27
Pharmacological differences between memory consolidation of habituation to an open field and inhibitory avoidance learning.
2001 Feb
NMDA receptor antagonist treatment induces a long-lasting increase in the number of proliferating cells, PSA-NCAM-immunoreactive granule neurons and radial glia in the adult rat dentate gyrus.
2001 Feb
Inorganic iron complexes derived from the nitric oxide donor nitroprusside: competitive N-methyl-D-aspartate receptor antagonists with nanomolar affinity.
2001 Feb 1
The anesthetic interaction between adenosine triphosphate and N-methyl-D-aspartate receptor antagonists in the rat.
2001 Jan
NMDA receptor antagonist AP5 and nitric oxide synthase inhibitor 7-NI affect different phases of learning and memory in goldfish.
2001 Jan 19
Antinociceptive effects after intrathecal administration of phosphodiester-, 2'-O-allyl-, and C-5-propyne-modified antisense oligodeoxynucleotides targeting the NMDAR1 subunit in mouse.
2001 Jan 31
Dopamine-independent locomotion following blockade of N-methyl-D-aspartate receptors in the ventral tegmental area.
2001 Jul
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
Effects of adult neurogenesis on synaptic plasticity in the rat dentate gyrus.
2001 Jun
Early onset of glutamatergic and GABAergic synaptic activity in the visual layers of the rodent superior colliculus.
2001 Jun
Amygdalar nmda receptors are critical for the expression of multiple conditioned fear responses.
2001 Jun 1
MAP2 phosphorylation and visual plasticity in Xenopus.
2001 Jun 29
Unipolar brush cells form a glutamatergic projection system within the mouse cerebellar cortex.
2001 Jun 4
Stimulatory effect of endothelin-1 on neurons in the nucleus tractus solitarii is mediated by non-N-methyl-D-aspartate receptors.
2001 Mar
Synergistic analgesic effects of intrathecal midazolam and NMDA or AMPA receptor antagonists in rats.
2001 Mar
Dopaminergic substantia nigra neurons express functional nmda receptors in postnatal rats.
2001 Mar
The analgesic interaction between intrathecal clonidine and glutamate receptor antagonists on thermal and formalin-induced pain in rats.
2001 Mar
Contribution of postsynaptic Ca2+ to the induction of post-tetanic potentiation in the neural circuit for siphon withdrawal in Aplysia.
2001 Mar 1
NMDA-responsible, APV-insensitive receptor in cultured human astrocytes.
2001 Mar 2
Effects of pituitary adenylate cyclase activating polypeptide on lumbosacral preganglionic neurons in the neonatal rat spinal cord.
2001 Mar 23
Quinolinic acid induces oxidative stress in rat brain synaptosomes.
2001 Mar 26
Neurophysiological correlates of delayed visual differentiation tasks in monkeys: the effects of the site of intracortical blockade of NMDA receptors.
2001 Mar-Apr
A kainate receptor increases the efficacy of GABAergic synapses.
2001 May
Regulation of spontaneous inhibitory synaptic transmission by endogenous glutamate via non-NMDA receptors in cultured rat hippocampal neurons.
2001 May
Short-term synaptic depression in the neonatal mouse spinal cord: effects of calcium and temperature.
2001 May
Electrophysiological characterization of "giant" cells in stratum radiatum of the CA3 hippocampal region.
2001 May
Polysynaptic excitatory pathways induce heterosynaptic depression in the rat auditory cortex.
2001 May
Characterization of spontaneous excitatory synaptic currents in pyramidal cells of rat prelimbic cortex.
2001 May 18
Stress-induced increase in extracellular dopamine in striatum: role of glutamatergic action via N-methyl-D-aspartate receptors in substantia nigra.
2001 May 18
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 05:27:22 UTC 2023
Edited
by admin
on Sat Dec 16 05:27:22 UTC 2023
Record UNII
39PJ29YY8Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
AP-5 (±)-
Code 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
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
Code System Code Type Description
PUBCHEM
1216
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
CAS
76326-31-3
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
WIKIPEDIA
2-Amino-5-phosphonovalerate
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
MESH
D015763
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
CHEBI
138644
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
FDA UNII
39PJ29YY8Z
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID90893701
Created by admin on Sat Dec 16 05:27:22 UTC 2023 , Edited by admin on Sat Dec 16 05:27:22 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Binds to glutamate site
COMPETITIVE INHIBITOR
ACTIVE ENANTIOMER->RACEMATE
Related Record Type Details
ACTIVE MOIETY