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α-MSH

CAT: 0804-HY-P0252-04Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-P0252-04Size:25 mg
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Description
α-MSH (α-Melanocyte-Stimulating Hormone), an endogenous neuropeptide, is an endogenous melanocortin receptor 4 (MC4R) agonist with anti-inflammatory and antipyretic activities. α-MSH is a post-translational derivative of pro-opiomelanocortin (POMC) [1][2].
CAS Number
581-05-5
Product Name Alternative
α-Melanocyte-Stimulating Hormone
UNSPSC
12352209
Target
Melanocortin Receptor
Type
Peptides
Related Pathways
GPCR/G Protein; Neuronal Signaling
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Metabolic Disease; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/_alpha_-Melanocyte-Stimulating_Hormone__MSH_,_amide.html
Purity
99.98
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : ≥ 12.5 mg/mL
Smiles
OC(C=C1)=CC=C1C[C@H](NC([C@H](CO)NC(C)=O)=O)C(N[C@@H](CO)C(N[C@@H](CCSC)C(N[C@@H](CCC(O)=O)C(N[C@@H](CC2=CN=CN2)C(N[C@@H](CC3=CC=CC=C3)C(N[C@@H](CCCNC(N)=N)C(N[C@H](C(NCC(N[C@@H](CCCCN)C(N4[C@@H](CCC4)C(N[C@H](C(N)=O)C(C)C)=O)=O)=O)=O)CC5=CNC6=CC=CC=C56)=O)=O)=O)=O)=O)=O)=O
Molecular Formula
C77H109N21O19S
Molecular Weight
1664.88
References & Citations
[1]Madhuri Singh, et al. C-terminal amino acids of alpha-melanocyte-stimulating hormone are requisite for its antibacterial activity against Staphylococcus aureus. Antimicrob Agents Chemother. 2011 May;55 (5) :1920-9.|[2]M S Kim, et al. Hypothalamic localization of the feeding effect of agouti-related peptide and alpha-melanocyte-stimulating hormone. Diabetes. 2000 Feb;49 (2) :177-82.|[3]Lipton JM, et al. Mechanisms of antiinflammatory action of alpha-MSH peptides. In vivo and in vitro evidence. Ann N Y Acad Sci. 1999;885:173-182.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture and light, under nitrogen)
Scientific Category
Peptides
Clinical Information
Phase 2
Isoform
MC4R

Chemical Information

Alpha-msh

Alpha-melanocyte stimulating hormone is a 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. It has a role as an anti-inflammatory agent.

CAS Number581-05-5
PubChem CID16133793
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
Molecular FormulaC77H109N21O19S
Molecular Weight1664.9
XLogP-4.3
Topological Polar Surface Area668
Hydrogen Bond Donor Count23
Hydrogen Bond Acceptor Count23
Rotatable Bond Count51
Heavy Atom Count118
Formal Charge0
Complexity3370
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
InChI
InChI=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
InChIKey
WHNFPRLDDSXQCL-UAZQEYIDSA-N
Chemical Structure
2D Structure
2D structure of Alpha-msh
CAS: 581-05-5
CID: 16133793
Formula: C77H109N21O19S
MW: 1664.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1664.9
XLogP3-4.3
Hydrogen Bond Donor Count23
Hydrogen Bond Acceptor Count23
Rotatable Bond Count51
Exact Mass1663.79293151
Monoisotopic Mass1663.79293151
Topological Polar Surface Area668 Ų
Heavy Atom Count118
Formal Charge0
Complexity3370
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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