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CHEBI:195325 - α-melanocyte stimulating hormone

ChEBI IDCHEBI:195325
ChEBI Nameα-melanocyte stimulating hormone
Stars
ASCII Namealpha-melanocyte stimulating hormone
DefinitionA 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.
Last Modified12 July 2023
Submitterwctseng
DownloadsMolfile
FormulaC77H109N21O19S
Net Charge0
Average Mass1664.914
Monoisotopic Mass1663.79293
SMILESCSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1cncn1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1cnc2ccccc12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(N)=O)C(C)C
InChIInChI=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
InChIKeyWHNFPRLDDSXQCL-UAZQEYIDSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
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  Source
Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2ChEBI
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-NH2ChEBI
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-valinamideChEBI
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-NH2ChEBI
intermedinSUBMITTER
melanotropinSUBMITTER
Manual XrefsDatabases
Alpha-Melanocyte-stimulating_hormoneWikipedia
Registry NumbersSources
Reaxys:741840Reaxys
CAS:581-05-5ChEBI
Citations