cyclo(L-His-L-Pro) (CHEBI:90039)

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CHEBI:90039 - cyclo(L-His-L-Pro)

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ChEBI ID	CHEBI:90039
ChEBI Name	cyclo(L-His-L-Pro)
Stars
ASCII Name	cyclo(L-His-L-Pro)
Definition	A homodetic cyclic peptide resulting from the formal condensation of both the amino and acid groups of L-histidine with the acid and amino groups of L-proline. It is a metabolite of thyrotropin-releasing hormone (TRH).
Secondary ChEBI ID	CHEBI:41471
Last Modified	25 October 2022
Downloads	Molfile

Formula	C11H14N4O2
Net Charge	0
Average Mass	234.259
Monoisotopic Mass	234.11168
SMILES	[H][C@@]12CCCN1C(=O)[C@H](Cc1cncn1)NC2=O
InChI	InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1
InChIKey	NAKUGCPAQTUSBE-IUCAKERBSA-N

Species of Metabolite	Component	Source	Comments
Homo sapiens (ncbitaxon:9606)
	blood serum (BTO:0000133)	PubMed (6401750)
	brain (BTO:0000142)	PubMed (6672793)

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	dopamine uptake inhibitor A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake. human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples.
Applications:	anti-inflammatory agent Any compound that has anti-inflammatory effects. dopamine uptake inhibitor A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.

ChEBI Ontology

Outgoing Relation(s)
	cyclo(L-His-L-Pro) (CHEBI:90039) has functional parent L-histidine (CHEBI:15971)
	cyclo(L-His-L-Pro) (CHEBI:90039) has functional parent L-proline (CHEBI:17203)
	cyclo(L-His-L-Pro) (CHEBI:90039) has role anti-inflammatory agent (CHEBI:67079)
	cyclo(L-His-L-Pro) (CHEBI:90039) has role dopamine uptake inhibitor (CHEBI:51039)
	cyclo(L-His-L-Pro) (CHEBI:90039) has role human blood serum metabolite (CHEBI:85234)
	cyclo(L-His-L-Pro) (CHEBI:90039) is a dipeptide (CHEBI:46761)
	cyclo(L-His-L-Pro) (CHEBI:90039) is a homodetic cyclic peptide (CHEBI:24613)
	cyclo(L-His-L-Pro) (CHEBI:90039) is a imidazoles (CHEBI:24780)
	cyclo(L-His-L-Pro) (CHEBI:90039) is a pyrrolopyrazine (CHEBI:48337)

IUPAC Name
(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Synonyms	Source
cyclo(His-Pro)	ChemIDplus
His-Pro-DKP	ChEBI
cyclo(histidyl-prolyl)	ChEBI
histidyl-proline-diketopiperazine	ChEBI
histidyl-proline diketopiperazine	ChEBI
L,L-cyclo(histidylprolyl)	ChEBI

UniProt Name	Source
L-histidyl-L-proline diketopiperazine	UniProt

Manual Xrefs	Databases
HMDB0002053	HMDB
FDB022818	FooDB
CHQ	PDBeChem

Registry Numbers	Sources
CAS:53109-32-3	ChemIDplus

Citations