CHEBI:136034 - afamelanotide

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ChEBI Name afamelanotide ChEBI ID CHEBI:136034 Definition A polypeptide comprising of 13 amino acids which is an analogue of α-melanocyte stimulating hormone. It is approved as a dermatologic drug for the prevention of phototoxicity in adult patients with erythropoietic protoporphyria. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Read full article at Wikipedia Formula C78H111N21O19 Net Charge 0 Average Mass 1646.874 Monoisotopic Mass 1645.83651 InChI InChI=1S/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1 InChIKey UAHFGYDRQSXQEB-LEBBXHLNSA-N SMILES CCCC[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 ) Application(s): dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin. View more via ChEBI Ontology ChEBI Ontology Outgoing afamelanotide (CHEBI:136034) has role dermatologic drug (CHEBI:50177) afamelanotide (CHEBI:136034) is a polypeptide (CHEBI:15841) IUPAC Name N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-α-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide INNs Sources afamelanotida WHO MedNet afamélanotide WHO MedNet afamelanotide WHO MedNet afamelanotidum WHO MedNet Synonyms Sources 4-Nle-7-Phe-alpha-MSH ChemIDplus [Nle4,D-Phe7]-α-MSH ChEBI Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 ChEBI CUV 1647 ChemIDplus CUV-1647 ChEBI CUV1647 ChemIDplus melanotan I ChemIDplus melanotan-1 ChemIDplus N-acteyl-L-Ser-L-Tyr-L-Ser-L-Nle-L-Glu-L-His-D-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-Val-NH2 ChEBI NDP-α-MSH ChEBI NDP-MSH ChemIDplus Nle4-D-Phe7-α-melanocyte-stimulating hormone ChEBI Brand Name Source Scenesse KEGG DRUG Manual Xrefs Databases 4836 DrugCentral Afamelanotide Wikipedia D10511 KEGG DRUG DB04931 DrugBank NZ554427 Patent View more database links Registry Number Type Source 75921-69-6 CAS Registry Number ChemIDplus Citations Types Sources 16293341 PubMed citation Europe PMC 16647700 PubMed citation Europe PMC 19144952 PubMed citation Europe PMC 21073357 PubMed citation Europe PMC 21597671 PubMed citation Europe PMC 23277150 PubMed citation Europe PMC 23407924 PubMed citation Europe PMC 23884489 PubMed citation Europe PMC 25230094 PubMed citation Europe PMC 25402764 PubMed citation Europe PMC 25470471 PubMed citation Europe PMC 25494545 PubMed citation Europe PMC 25607635 PubMed citation Europe PMC 25607828 PubMed citation Europe PMC 26132941 PubMed citation Europe PMC 26979527 PubMed citation Europe PMC 28003770 PubMed citation Europe PMC 28063031 PubMed citation Europe PMC 30517779 PubMed citation Europe PMC 31660977 PubMed citation Europe PMC 31987791 PubMed citation Europe PMC 32186677 PubMed citation Europe PMC 32459219 PubMed citation Europe PMC 32811524 PubMed citation Europe PMC Last Modified 08 October 2020