Chemicals and Drugs

alpha-MSH

A 13-amino acid peptide derived from proteolytic cleavage of ADRENOCORTICOTROPIC HORMONE, the N-terminal segment of ACTH. ACTH (1-13) is amidated at the C-terminal to form ACTH (1-13)NH2 which in turn is acetylated to form alpha-MSH in the secretory granules. Alpha-MSH stimulates the synthesis and distribution of MELANIN in MELANOCYTES in mammals and MELANOPHORES in lower vertebrates.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A 13-amino acid peptide derived from proteolytic cleavage of ADRENOCORTICOTROPIC HORMONE, the N-terminal segment of ACTH. ACTH (1-13) is amidated at the C-terminal to form ACTH (1-13)NH2 which in turn is acetylated to form alpha-MSH in the secretory granules. Alpha-MSH stimulates the synthesis and distribution of MELANIN in MELANOCYTES in mammals and MELANOPHORES in lower vertebrates.

Chemical Identity

Chemical Information

Molecular Formula
C77H109N21O19S
Molecular Weight
1664.9 g/mol
CAS Registry No.
581-05-5
IUPAC Name
(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-[[(2S)-1-[[(2S)-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 acid
InChIKey
WHNFPRLDDSXQCL-UAZQEYIDSA-N
SMILES
CC(C)[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)C
MeSH Unique ID
D000521
Source
PubChem CID 16133793

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

27 entry terms
  • Acetylated ACTH (1-13)NH2
  • MSH, alpha
  • alpha Intermedin
  • alpha-Melanocyte-Stimulating Hormone
  • alpha-Melanotropin
  • Hormone, alpha-Melanocyte-Stimulating
  • Intermedin, alpha
  • alpha MSH
  • alpha Melanocyte Stimulating Hormone
  • alpha Melanotropin
  • (Des-Acetyl)-alpha-MSH
  • (Desacetyl)alpha-MSH
  • ACTH (1-13)
  • ACTH (1-13)NH2
  • ACTH(1-13)
  • Adrenocorticotropin (1-13)NH2
  • DE-alpha-MSH
  • Des-Acetyl MSH
  • Desacetyl alpha-MSH
  • Desacetyl alpha-Melanocyte-Stimulating Hormone
  • MSH, (Desacetyl)alpha-
  • Desacetyl alpha MSH
  • Desacetyl alpha Melanocyte Stimulating Hormone
  • Hormone, Desacetyl alpha-Melanocyte-Stimulating
  • MSH, Des-Acetyl
  • alpha-MSH, Desacetyl
  • alpha-Melanocyte-Stimulating Hormone, Desacetyl

MeSH Record

Aspects Covered

30 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, deficiency, drug effects, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

1988 (1981)

MeSH Record

Previous Indexing

  • MSH (1966-1987)

MeSH Hierarchy

Tree Numbers

  1. D06.472w.699w.327.935.179w
  2. D06.472w.699w.327.935.531w.750w.050w
  3. D06.472w.699w.631.525.600.179w
  4. D06.472w.699w.631.525.600.531w.750w.050w
  5. D12.644w.400w.400.935.179w
  6. D12.644w.400w.400.935.531w.750w.050w
  7. D12.644w.400w.460w.050w
  8. D12.644w.548w.365.935.179w
  9. D12.644w.548w.365.935.531w.750w.050w
  10. D12.644w.548w.691.525.690.179w
  11. D12.644w.548w.691.525.690.531w.750w.050w
  12. D12.776w.631w.650w.405.935.179w
  13. D12.776w.631w.650w.405.935.531w.750w.050w
  14. D12.776w.631w.650w.460w.050w

AMA Style

References

  1. National Library of Medicine. alpha-MSH. Medical Subject Headings (MeSH). 2026. Unique ID D000521. http://id.nlm.nih.gov/mesh/2026/D000521
  2. alpha-MSH. In: Wikipedia. https://en.wikipedia.org/wiki/%CE%91-Melanocyte-stimulating_hormone
  3. alpha-MSH. In: Wikidata. https://www.wikidata.org/wiki/Q4063639
  4. alpha-MSH. In: PubChem Compound. CID 16133793. https://pubchem.ncbi.nlm.nih.gov/compound/16133793