Afamelanotide
(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Molecular Identity
Afamelanotide
(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
PubChem CID: 16197727
2D Structure
Properties
C78H111N21O19
Molecular Formula
1646.80
Molecular Weight
g/mol
1645.8365
Exact Mass
Da
-3.5
XLogP
Drug-like (Lipinski: < 5)
643
TPSA
May have limited oral absorption
23
H-Bond Donors
22
H-Bond Acceptors
3360
Complexity
SMILES
Canonical SMILES
SMILES: CCCCC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)NC(CCCCN)C(=O)N5CCCC5C(=O)NC(C(C)C)C(=O)N)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CO)NC(=O)CIsomeric SMILES
SMILES: CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N5CCC[C@H]5C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)CSynonyms(20)
AfamelanotideMelanotan4-Norleucyl-7-phenylalanine-alpha-mshDTXSID40226843NDPMSH(Nle(4),D-Phe(7))alpha-MSHRefChem:57383D02BB02DTXCID70149334(4S)-4-(((2S)-2-(((2S)-2-(((2S)-2-(((2S)-2-acetamido-3-hydroxypropanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-3-hydroxypropanoyl)amino)hexanoyl)amino)-5-(((2S)-1-(((2R)-1-(((2S)-1-(((2S)-1-((2-(((2S)-6-amino-1-((2S)-2-(((2S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxohexan-2-yl)amino)-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-5-carbamimidamido-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid4-Nle-7-Phe-alpha-MSH75921-69-6Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2afamelanotidaafamelanotidum
Data from PubChem (NCBI)
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