Key facts
CAS number:75487-36-4,
Purity:>95%,
Form:SolidSee storage information,
Molecular weight:1664.9 Da,
Molecular formula:C77H109N21O19S,
PubChem:16132144,
Nature:Synthetic,
Solubility:Soluble in water,
Biochemical name:Msh, 2-tyr-alpha-,
Canonical smiles:CC(C)C(C(=O)N)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)CNC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC4=CC=CC=C4)NC(=O)C(CC5=CN=CN5)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CO)NC(=O)C,
Isomeric 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=CN=CN5)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,
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-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions--20°C, Appropriate long-term storage conditions--20°C, Storage information-Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
MC1-R MC2-R MC3-R and MC4-R are members of the melanocortin receptor family. These receptors interact with melanocyte-stimulating hormone (MSH) peptides important for various physiological functions. The mass varies among these receptors generally ranging between 30 to 40 kDa. MC1-R is predominantly expressed in melanocytes influencing skin pigmentation whereas MC2-R also known as the adrenocorticotropic hormone (ACTH) receptor is mainly found in the adrenal cortex. MC3-R and MC4-R have a wider distribution including the central nervous system and participate in different metabolic processes.
Biological function summary
Theta melanocortin receptors play significant roles in regulating diverse processes from pigmentation to energy homeostasis. These receptors act independently and do not appear to form larger stable complexes. For instance MC1-R activation by alpha-melanocyte-stimulating hormone (alpha-MSH) increases melanin synthesis in melanocytes leading to skin darkening. In contrast MC4-R is key in controlling energy balance within the brain where it influences appetite and energy expenditure.
Pathways
Interactions between melanocortin receptors and their ligand MSH hormone play a pivotal role in the signaling pathways regulating skin pigmentation and appetite suppression. MC1-R is part of the pathway that enhances melanin production through the activation of adenylate cyclase followed by cAMP production. MC4-R fits into the central melanocortin pathway which is critical for energy homeostasis and involves proteins like Agouti-related protein (AgRP) as an antagonist. These pathways demonstrate the diverse roles of MSH receptor activities in vertebrate biology.
Variations in melanocortin receptors connect to conditions like obesity and Addison's disease. Mutations or dysfunctions in MC4-R often correlate with genetic forms of obesity due to impaired appetite control. Similarly abnormalities in MC2-R are linked to Addison's disease where ACTH signaling to the adrenal glands becomes disrupted affecting cortisol production. The interaction with proteins like proopiomelanocortin (POMC) the precursor of ACTH and MSH highlights the importance of these receptors in disease manifestations.
