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CHEBI:136034 - afamelanotide

ChEBI IDCHEBI:136034
ChEBI Nameafamelanotide
Stars
DefinitionA 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.
Last Modified8 October 2020
DownloadsMolfile
FormulaC78H111N21O19
Net Charge0
Average Mass1646.874
Monoisotopic Mass1645.83651
SMILESCCCC[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/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
InChIKeyUAHFGYDRQSXQEB-LEBBXHLNSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Application:
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
ChEBI Ontology
Outgoing Relation(s)
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  Source
afamelanotidaWHO MedNet
afamelanotidumWHO MedNet
afamelanotideWHO MedNet
afamélanotideWHO MedNet
Synonyms  Source
melanotan IChemIDplus
CUV 1647ChemIDplus
CUV1647ChemIDplus
Nle4-D-Phe7-α-melanocyte-stimulating hormoneChEBI
CUV-1647ChEBI
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-NH2ChEBI
Brand Name  Source
ScenesseKEGG DRUG
Manual XrefsDatabases
4836DrugCentral
DB04931DrugBank
D10511KEGG DRUG
AfamelanotideWikipedia
NZ554427Patent
Registry NumbersSources
CAS:75921-69-6ChemIDplus
Citations