midafotel (CHEBI:180900)

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ChEBI Name	midafotel

ChEBI ID	CHEBI:180900

Definition	A member of the class of piperazines that is piperazine substituted by a carboxy group at position 2R and a (1E)-1-phosphonoprop-1-en-3-yl group at position 4. It is an antagonist of N-methyl-D-aspartate receptors (NMDARs) and was in clinical development by Novartis for the treatment of cognition disorders and brain injuries (now discontinued).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Stan Laulederkind

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Formula

C8H15N2O5P

Net Charge

Average Mass

250.191

Monoisotopic Mass

250.07186

InChI

InChI=1S/C8H15N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h1,5,7,9H,2-4,6H2,(H,11,12)(H2,13,14,15)/b5-1+/t7-/m1/s1

InChIKey

VZXMZMJSGLFKQI-ABVWVHJUSA-N

SMILES

OC(=O)[C@H]1CN(C\C=C\P(O)(O)=O)CCN1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	NMDA receptor antagonist Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. anticonvulsant A drug used to prevent seizures or reduce their severity.

ChEBI Ontology
Outgoing	midafotel (CHEBI:180900) has role anticonvulsant (CHEBI:35623) midafotel (CHEBI:180900) has role neuroprotective agent (CHEBI:63726) midafotel (CHEBI:180900) has role NMDA receptor antagonist (CHEBI:60643) midafotel (CHEBI:180900) is a monocarboxylic acid (CHEBI:25384) midafotel (CHEBI:180900) is a olefinic compound (CHEBI:78840) midafotel (CHEBI:180900) is a phosphonic acids (CHEBI:26069) midafotel (CHEBI:180900) is a piperazinecarboxylic acid (CHEBI:48683) midafotel (CHEBI:180900) is a tertiary amino compound (CHEBI:50996)

IUPAC Name

(2R)-4-[(2E)-3-phosphonoprop-2-en-1-yl]piperazine-2-carboxylic acid

Synonyms	Sources
(2R)-4-[(2E)-3-phosphono-2-propenyl]-2-piperazinecarboxylic acid	ChEBI
(R)-4-[(E)-3-phosphonoprop-2-enyl]piperazine-2-carboxylic acid	ChEBI
(R)-CPP-ene	ChEBI
D(−)CPPene	ChEBI
D-4-[(2E)-3-phosphono-2-propenyl]-2-piperazinecarboxylic acid	ChEBI
D-CPP-ene	ChemIDplus
D-CPPene	SUBMITTER
SDZ EAA 494	ChEBI
SDZ-EAA 494	ChemIDplus
SDZ-EAA-494	SUBMITTER

Registry Number	Type	Source
117414-74-1	CAS Registry Number	ChemIDplus

Last Modified

04 November 2021