CHEBI:195325 - α-melanocyte stimulating hormone

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ChEBI Name α-melanocyte stimulating hormone
ChEBI ID CHEBI:195325
ChEBI ASCII Name alpha-melanocyte stimulating hormone
Definition A thirteen amino acid peptide hormone consisting of N-acetyl-L-Ser, L-Tyr, L-Ser, L-Met, L-Glu, L-His, L-Phe, L-Arg, L-Trp, Gly, L-Lys, L-Pro and L-valinamide units joined in sequence by peptide linkages. It is an endogenous melanocortin receptor agonist that exhibits anti-inflammatory activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Wei-Chia Tseng
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Formula C77H109N21O19S
Net Charge 0
Average Mass 1664.910
Monoisotopic Mass 1663.79293
InChI InChI=1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,64-/m0/s1
InChIKey WHNFPRLDDSXQCL-UAZQEYIDSA-N
SMILES CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O
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): 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): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing α-melanocyte stimulating hormone (CHEBI:195325) has role anti-inflammatory agent (CHEBI:67079)
α-melanocyte stimulating hormone (CHEBI:195325) is a peptide hormone (CHEBI:25905)
IUPAC Name
N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-methionyl-L-α-glutamyl-L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide
Synonyms Sources
Ac-L-Ser-L-Tyr-L-Ser-L-Met-L-Glu-L-His-L-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-Val-NH2 ChEBI
Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 ChEBI
α-intermedin ChEBI
α-melanotropin ChEBI
α-MSH ChEBI
intermedin SUBMITTER
melanotropin SUBMITTER
melanotropin α SUBMITTER
N-Ac-L-Ser-L-Tyr-L-Ser-L-Met-L-Glu-L-His-L-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-Val-NH2 ChEBI
N-acetyl-L-Ser-L-Tyr-L-Ser-L-Met-L-α-Glu-L-His-L-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-valinamide ChEBI
Manual Xref Database
Alpha-Melanocyte-stimulating_hormone Wikipedia
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Registry Numbers Types Sources
581-05-5 CAS Registry Number ChEBI
741840 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
33210000 PubMed citation Europe PMC
33523420 PubMed citation Europe PMC
33639356 PubMed citation Europe PMC
33765043 PubMed citation Europe PMC
34904527 PubMed citation Europe PMC
35717488 PubMed citation Europe PMC
35733058 PubMed citation Europe PMC
36900442 PubMed citation Europe PMC
37001274 PubMed citation Europe PMC
37217094 PubMed citation Europe PMC
Last Modified
12 July 2023