CHEBI:75431 - ghrelin

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ChEBI Name ghrelin
ChEBI ID CHEBI:75431
Definition A 28-membered appetite-stimulating polypeptide consisting of Gly, Ser, Ser(octanoyl), Phe, Leu, Ser, Pro, Glu, His, Gln, Arg, Val, Gln, Gln, Arg, Lys, Glu, Ser, Lys, Lys, Pro, Pro, Ala, Lys, Leu, Gln, Pro and Arg residues joined in sequence. The O-n-octanoylation of the side-chain hydroxy group of serine-3 (Ser3) is essential for ghrelin's activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C149H249N47O42
Net Charge 0
Average Mass 3370.867
Monoisotopic Mass 3368.87933
InChI InChI=1S/C149H249N47O42/c1-9-10-11-12-16-45-118(209)238-78-106(191-135(225)103(75-197)171-115(204)73-154)137(227)187-101(71-84-32-14-13-15-33-84)133(223)186-100(70-81(4)5)132(222)190-105(77-199)144(234)194-66-29-42-108(194)139(229)180-95(51-57-117(207)208)128(218)188-102(72-85-74-165-79-169-85)134(224)179-92(47-53-112(156)201)126(216)175-90(39-26-63-167-148(161)162)130(220)192-119(82(6)7)141(231)181-93(48-54-113(157)202)127(217)177-91(46-52-111(155)200)125(215)174-89(38-25-62-166-147(159)160)122(212)173-87(35-18-22-59-151)121(211)178-94(50-56-116(205)206)129(219)189-104(76-198)136(226)176-88(36-19-23-60-152)123(213)182-96(37-20-24-61-153)142(232)196-68-31-44-110(196)145(235)195-67-30-41-107(195)138(228)170-83(8)120(210)172-86(34-17-21-58-150)124(214)185-99(69-80(2)3)131(221)183-97(49-55-114(158)203)143(233)193-65-28-43-109(193)140(230)184-98(146(236)237)40-27-64-168-149(163)164/h13-15,32-33,74,79-83,86-110,119,197-199H,9-12,16-31,34-73,75-78,150-154H2,1-8H3,(H2,155,200)(H2,156,201)(H2,157,202)(H2,158,203)(H,165,169)(H,170,228)(H,171,204)(H,172,210)(H,173,212)(H,174,215)(H,175,216)(H,176,226)(H,177,217)(H,178,211)(H,179,224)(H,180,229)(H,181,231)(H,182,213)(H,183,221)(H,184,230)(H,185,214)(H,186,223)(H,187,227)(H,188,218)(H,189,219)(H,190,222)(H,191,225)(H,192,220)(H,205,206)(H,207,208)(H,236,237)(H4,159,160,166)(H4,161,162,167)(H4,163,164,168)/t83-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,119-/m0/s1
InChIKey GNKDKYIHGQKHHM-RJKLHVOGSA-N
SMILES C(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N1[C@@H](CCC1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N2[C@@H](CCC2)C(N3[C@@H](CCC3)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(N4[C@@H](CCC4)C(=O)N[C@H](C(=O)O)CCCNC(=N)N)=O)CCC(=O)N)CC(C)C)CCCCN)C)=O)=O)CCCCN)CCCCN)CO)CCC(=O)O)CCCCN)CCCNC(N)=N)CCC(=O)N)CCC(=O)N)C(C)C)CCCNC(N)=N)CCC(=O)N)CC=5N=CNC5)CCC(=O)O)=O)CO)CC(C)C)CC=6C=CC=CC6)COC(=O)CCCCCCC)CO)N
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 metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via peptide hormone )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiatherogenic agent
A cardiovascular drug that prevents atherogenesis, the accumulation of lipid-containing plaques on the innermost layers of the arteries. Compare with antiatherosclerotic agent.
appetite enhancer
A drug which increases appetite.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ghrelin (CHEBI:75431) has role antiatherogenic agent (CHEBI:50855)
ghrelin (CHEBI:75431) has role antineoplastic agent (CHEBI:35610)
ghrelin (CHEBI:75431) has role apoptosis inducer (CHEBI:68495)
ghrelin (CHEBI:75431) has role appetite enhancer (CHEBI:50779)
ghrelin (CHEBI:75431) has role human metabolite (CHEBI:77746)
ghrelin (CHEBI:75431) is a peptide hormone (CHEBI:25905)
ghrelin (CHEBI:75431) is a polypeptide (CHEBI:15841)
IUPAC Name
glycyl-L-seryl-O-octanoyl-L-seryl-L-phenylalanyl-L-leucyl-L-seryl-L-prolyl-L-α-glutamyl-L-histidyl-L-glutaminyl-L-arginyl-L-valyl-L-glutaminyl-L-glutaminyl-L-arginyl-L-lysyl-L-α-glutamyl-L-seryl-L-lysyl-L-lysyl-L-prolyl-L-prolyl-L-alanyl-L-lysyl-L-leucyl-L-glutaminyl-L-prolyl-L-arginine
INNs Sources
lenomorelin WHO MedNet
lenomorelina WHO MedNet
lénomoréline WHO MedNet
lenomorelinum WHO MedNet
Synonyms Sources
Gastric MLTRP ChemIDplus
Ghrelin (human) ChemIDplus
Gly-Ser-Ser(octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Arg-Val-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg ChEBI
GS-S(n-octanoyl)-FLSPEHQRVQQRKESKKPPAKLQPR ChEBI
GSS(octanoyl)FLSPEHQRVQQRKESKKPPAKLQPR ChEBI
H-Gly-Ser-Ser(n-octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Arg-Val-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg-OH ChEBI
Human ghrelin ChemIDplus
Motilin-related peptide ChemIDplus
Manual Xrefs Databases
C16025 KEGG COMPOUND
Ghrelin Wikipedia
View more database links
Registry Numbers Types Sources
24715767 Reaxys Registry Number Reaxys
258279-04-8 CAS Registry Number ChemIDplus
304853-26-7 CAS Registry Number ChemIDplus
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Last Modified
25 July 2017