CHEBI:138186 - p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe

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ChEBI Name p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe
ChEBI ID CHEBI:138186
Definition A thirteen-membered polypeptide consisting of p-Glu, Arg, Pro, Arg, Leu, Ser, His, Lys, Gly, Pro, Met, Pro and Phe residues joined in sequence.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C69H108N22O16S
Net Charge 0
Average Mass 1533.802
Monoisotopic Mass 1532.80344
InChI InChI=1S/C69H108N22O16S/c1-39(2)32-47(85-57(96)43(17-9-26-76-68(71)72)82-63(102)52-20-12-29-90(52)65(104)45(18-10-27-77-69(73)74)83-58(97)44-22-23-54(93)80-44)59(98)88-50(37-92)61(100)86-48(34-41-35-75-38-79-41)60(99)81-42(16-7-8-25-70)56(95)78-36-55(94)89-28-11-19-51(89)62(101)84-46(24-31-108-3)66(105)91-30-13-21-53(91)64(103)87-49(67(106)107)33-40-14-5-4-6-15-40/h4-6,14-15,35,38-39,42-53,92H,7-13,16-34,36-37,70H2,1-3H3,(H,75,79)(H,78,95)(H,80,93)(H,81,99)(H,82,102)(H,83,97)(H,84,101)(H,85,96)(H,86,100)(H,87,103)(H,88,98)(H,106,107)(H4,71,72,76)(H4,73,74,77)/t42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
InChIKey GGMAXEWLXWJGSF-PEWBXTNBSA-N
SMILES N([C@H](C(=O)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(=O)NCC(N1[C@@H](CCC1)C(=O)N[C@H](C(N2[C@@H](CCC2)C(=O)N[C@H](C(O)=O)CC=3C=CC=CC3)=O)CCSC)=O)CCCCN)=O)CC=4N=CNC4)=O)CO)=O)CC(C)C)CCCNC(=N)N)C(=O)[C@H]5N(C([C@@H](NC([C@H]6NC(CC6)=O)=O)CCCNC(=N)N)=O)CCC5
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) 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): apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186) has role apoptosis inhibitor (CHEBI:68494)
p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186) has role human metabolite (CHEBI:77746)
p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186) has role neuroprotective agent (CHEBI:63726)
p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186) is a polypeptide (CHEBI:15841)
p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186) is tautomer of [Pyr1]apelin-13(2+) (CHEBI:147415)
Incoming [Pyr1]apelin-13(2+) (CHEBI:147415) is tautomer of p-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe (CHEBI:138186)
IUPAC Name
5-oxo-L-prolyl-L-arginyl-L-prolyl-L-arginyl-L-leucyl-L-seryl-L-histidyl-L-lysylglycyl-L-prolyl-L-methionyl-L-prolyl-L-phenylalanine
Synonyms Sources
(pGlu1)apelin-13 ChemIDplus
[Pyr1]-apelin-13 ChEBI
[Pyr1]apelin-13 ChEBI
L-p-Glu-L-Arg-L-Pro-L-Arg-L-Leu-L-Ser-L-His-L-Lys-Gly-L-Pro-L-Met-L-Pro-L-Phe ChEBI
p-Glu-RPRLSHKGPMPF ChEBI
Pyr-apelin-13 ChemIDplus
Registry Numbers Types Sources
217082-60-5 CAS Registry Number ChemIDplus
31297008 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15582714 PubMed citation Europe PMC
19597036 PubMed citation Europe PMC
23727032 PubMed citation Europe PMC
24728860 PubMed citation Europe PMC
25443792 PubMed citation Europe PMC
26394665 PubMed citation Europe PMC
27492965 PubMed citation Europe PMC
27916097 PubMed citation Europe PMC
28087150 PubMed citation Europe PMC
28137936 PubMed citation Europe PMC
28181211 PubMed citation Europe PMC
28293165 PubMed citation Europe PMC
28681996 PubMed citation Europe PMC
Last Modified
15 August 2017