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

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ChEBI Name	cyclo(L-His-L-Pro)

ChEBI ID	CHEBI:90039

ChEBI 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).

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

Secondary ChEBI IDs	CHEBI:41471

Supplier Information

Download	Molfile XML SDF

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Formula

C11H14N4O2

Net Charge

Average Mass

234.259

Monoisotopic Mass

234.11168

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

SMILES

O=C1N2CCC[C@]2(C(=O)N[C@H]1CC=3NC=NC3)[H]

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in blood serum (BTO:0000133). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in brain (BTO:0000142). See: PubMed

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

Biological Role(s):	human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. 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.

Application(s):	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. anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	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	Sources
cyclo(His-Pro)	ChemIDplus
cyclo(histidyl-prolyl)	ChEBI
cyclo(L-His-L-Pro)	ChEBI
His-Pro-DKP	ChEBI
histidyl-proline diketopiperazine	ChEBI
histidyl-proline-diketopiperazine	ChEBI
histidylproline diketopiperazine	ChEBI
L,L-cyclo(histidylprolyl)	ChEBI
L-His-L-Pro-DKP	ChEBI
L-histidyl-L-proline diketopiperazine	UniProt

Registry Number	Type	Source
53109-32-3	CAS Registry Number	ChemIDplus

Last Modified

25 October 2022

General Comment
2019-11-04	Please note that the structure provided in HMDB and FooDB for histidylproline diketopiperazine is incorrect.