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SHU-9119

CAS No.:
168482-23-3
Catalog Number:
AG00APCS
Molecular Formula:
C56H72F3N15O11
Molecular Weight:
1188.2600
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$187
- +
5mg
98%
1 week
United States
$707
- +
Product Description
Catalog Number:
AG00APCS
Chemical Name:
SHU-9119
CAS Number:
168482-23-3
Molecular Formula:
C56H72F3N15O11
Molecular Weight:
1188.2600
IUPAC Name:
(3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-acetamidohexanoyl]amino]-6-[3-(diaminomethylideneamino)propyl]-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-9-(naphthalen-2-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxamide
InChI:
InChI=1S/C54H71N15O9/c1-3-4-15-40(63-31(2)70)48(73)69-45-27-46(71)59-21-10-9-17-39(47(55)72)64-51(76)43(25-35-28-61-38-16-8-7-14-37(35)38)67-49(74)41(18-11-22-60-54(56)57)65-50(75)42(24-32-19-20-33-12-5-6-13-34(33)23-32)66-52(77)44(68-53(45)78)26-36-29-58-30-62-36/h5-8,12-14,16,19-20,23,28-30,39-45,61H,3-4,9-11,15,17-18,21-22,24-27H2,1-2H3,(H2,55,72)(H,58,62)(H,59,71)(H,63,70)(H,64,76)(H,65,75)(H,66,77)(H,67,74)(H,68,78)(H,69,73)(H4,56,57,60)/t39-,40-,41-,42+,43-,44-,45-/m0/s1
InChI Key:
GGYWLZFXFKFWKL-XOJVSUSESA-N
SMILES:
OC(=O)C(F)(F)F.CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)Cc1[nH]cnc1)Cc1ccc2c(c1)cccc2)CCCNC(=N)N)Cc1c[nH]c2c1cccc2)C(=O)N)NC(=O)C
Properties
Complexity:
2090  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
0
Exact Mass:
1073.556g/mol
Formal Charge:
0
Heavy Atom Count:
78  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
13  
Isotope Atom Count:
0
Molecular Weight:
1074.258g/mol
Monoisotopic Mass:
1073.556g/mol
Rotatable Bond Count:
17  
Topological Polar Surface Area:
385A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.3  
Literature
Title Journal
Synthesis and evaluation of bivalent ligands for binding to the human melanocortin-4 receptor. Bioorganic & medicinal chemistry 20141115
The effect of melanocortin (Mc3 and Mc4) antagonists on serotonin-induced food and water intake of broiler cockerels. Journal of veterinary science 20120901
Activation of the central melanocortin system contributes to the increased arterial pressure in obese Zucker rats. American journal of physiology. Regulatory, integrative and comparative physiology 20120301
The HPA axis modulates the CNS melanocortin control of liver triacylglyceride metabolism. Physiology & behavior 20120201
Neuronostatin induces hyperalgesia in formalin test in mice. Neuroscience letters 20120106
Central administration of neuronostatin induces antinociception in mice. Peptides 20110901
Intracerebroventricular administration of neuronostatin induces depression-like effect in forced swim test of mice. Peptides 20110901
Inflammation-induced lethargy is mediated by suppression of orexin neuron activity. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110803
The melanocortin system is involved in regulating autonomic nerve activity through central pituitary adenylate cyclase-activating polypeptide. Neuroscience research 20110501
Melanocortin activity in the amygdala influences alcohol intake. Pharmacology, biochemistry, and behavior 20110301
Thyroid transcription factor-1 regulates feeding behavior via melanocortin pathway in the hypothalamus. Diabetes 20110301
Activation of the melanocortin-4 receptor causes enhanced excitation in presympathetic paraventricular neurons in obese Zucker rats. Regulatory peptides 20110117
Visfatin induces sickness responses in the brain. PloS one 20110101
Solution structures and molecular interactions of selective melanocortin receptor antagonists. Molecules and cells 20101201
The endogenous actions of hypothalamic peptides on brown adipose tissue thermogenesis in the rat. Endocrinology 20100901
Agrp neurons mediate Sirt1's action on the melanocortin system and energy balance: roles for Sirt1 in neuronal firing and synaptic plasticity. The Journal of neuroscience : the official journal of the Society for Neuroscience 20100901
Enhanced blood pressure and appetite responses to chronic central melanocortin-3/4 receptor blockade in dietary-induced obesity. Journal of hypertension 20100701
A concise synthesis of 1,4-dihydro-[1,4]diazepine-5,7-dione, a novel 7-TM receptor ligand core structure with melanocortin receptor agonist activity. Bioorganic & medicinal chemistry 20100301
Role of central leptin signaling in renal macrophage infiltration. Endocrine journal 20100101
Distinct effects of leptin and a melanocortin receptor agonist injected into medial hypothalamic nuclei on glucose uptake in peripheral tissues. Diabetes 20091201
A functional melanocortin system may be required for chronic CNS-mediated antidiabetic and cardiovascular actions of leptin. Diabetes 20090801
Mediobasal hypothalamic leucine sensing regulates food intake through activation of a hypothalamus-brainstem circuit. The Journal of neuroscience : the official journal of the Society for Neuroscience 20090701
Hindbrain leptin stimulation induces anorexia and hyperthermia mediated by hindbrain melanocortin receptors. Endocrinology 20090401
Pituitary adenylate cyclase-activating polypeptide inhibits food intake in mice through activation of the hypothalamic melanocortin system. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090101
Xenin, a gastrointestinal peptide, regulates feeding independent of the melanocortin signaling pathway. Diabetes 20090101
Gestational weight gain by reduced brain melanocortin activity affects offspring energy balance in rats. International journal of obesity (2005) 20090101
Peripheral antinociceptive effects of MC4 receptor antagonists in a rat model of neuropathic pain - a biochemical and behavioral study. Pharmacological reports : PR 20090101
Mechanisms mediating renal sympathetic activation to leptin in obesity. American journal of physiology. Regulatory, integrative and comparative physiology 20081201
Brain apolipoprotein E: an important regulator of food intake in rats. Diabetes 20080801
Agouti-related peptide and MC3/4 receptor agonists both inhibit excitatory hypothalamic ventromedial nucleus neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20080521
Endogenous melanocortin system activity contributes to the elevated arterial pressure in spontaneously hypertensive rats. Hypertension (Dallas, Tex. : 1979) 20080401
A derivative of the melanocortin receptor antagonist SHU9119 (PG932) increases food intake when administered peripherally. Peptides 20080101
The central melanocortin system directly controls peripheral lipid metabolism. The Journal of clinical investigation 20071101
Enterostatin inhibition of dietary fat intake is modulated through the melanocortin system. Peptides 20070301
Melanocortins and agouti-related protein modulate the excitability of two arcuate nucleus neuron populations by alteration of resting potassium conductances. The Journal of physiology 20070115
Functional characterization of the modified melanocortin peptides responsible for ligand selectivity at the human melanocortin receptors. Peptides 20061101
Cell signaling and trafficking of human melanocortin receptors in real time using two-photon fluorescence and confocal laser microscopy: differentiation of agonists and antagonists. Chemical biology & drug design 20061001
Cardiovascular effects of adrenocorticotropin microinjections into the rostral ventrolateral medullary pressor area of the rat. Brain research 20060802
Activation of the melanocortin-4 receptor mobilizes intracellular free calcium in immortalized hypothalamic neurons. The Journal of surgical research 20060515
Effects of central leptin infusion on the reward-potentiating effect of D-amphetamine. Brain research 20060504
Melanocortin modulation of inflammatory cytokine and neuroendocrine responses to endotoxin in the monkey. Endocrinology 20060401
Molecular characterization of human melanocortin-3 receptor ligand-receptor interaction. Biochemistry 20060131
Effect of the melanocortin receptor stimulation or inhibition on ethanol intake in alcohol-preferring rats. Peptides 20060101
Feeding, body weight, and sensitivity to non-ingestive reward stimuli during and after 12-day continuous central infusions of melanocortin receptor ligands. Peptides 20051101
Inhibition of morphine tolerance by spinal melanocortin receptor blockade. Pain 20051001
Activation of melanocortin receptors accelerates the gonadotropin-releasing hormone pulse generator activity in goats. Neuroscience letters 20050805
Effects of high-fat diets with different carbohydrate-to-protein ratios on energy homeostasis in rats with impaired brain melanocortin receptor activity. American journal of physiology. Regulatory, integrative and comparative physiology 20050701
Adrenocorticotropin evokes transient elevations in intracellular free calcium ([Ca2+]i) and increases basal [Ca2+]i in resting chondrocytes through a phospholipase C-dependent mechanism. Endocrinology 20050701
Functional selectivity of melanocortin 4 receptor peptide and nonpeptide agonists: evidence for ligand-specific conformational states. The Journal of pharmacology and experimental therapeutics 20050601
Blockade of melanocortin transmission inhibits cocaine reward. The European journal of neuroscience 20050401
alpha-MSH and gamma-MSH inhibit IL-1beta induced activation of the hypothalamic-pituitary-adrenal axis through central melanocortin receptors. Regulatory peptides 20041115
Activation of MAP kinase by MC4-R through PI3 kinase. Regulatory peptides 20040815
Agouti-related protein antagonizes glucocorticoid production induced through melanocortin 4 receptor activation in bovine adrenal cells: a possible autocrine control. Endocrinology 20040201
Agonist-dependent internalization of the human melanocortin-4 receptors in human embryonic kidney 293 cells. The Journal of pharmacology and experimental therapeutics 20031201
Interrelationships between mu opioid and melanocortin receptors in mediating food intake in rats. Brain research 20031121
The effect of morphine on MC4 and CRF receptor mRNAs in the rat amygdala and attenuation of tolerance after their blockade. Brain research 20031114
Extensive structure-activity studies of lactam derivatives of MT-II and SHU-9119: their activity and selectivity at human melanocortin receptors 3, 4, and 5. The journal of peptide research : official journal of the American Peptide Society 20031101
Further evidence that melanocortins prevent myocardial reperfusion injury by activating melanocortin MC3 receptors. European journal of pharmacology 20030923
Interaction between the spinal melanocortin and opioid systems in a rat model of neuropathic pain. Anesthesiology 20030801
Alpha-melanocyte-stimulating hormone stimulates prolactin secretion through melanocortin-3 receptors expressed in mammotropes in the mouse pituitary. Neuroendocrinology 20030801
Physiologic effect of leptin on insulin secretion is mediated mainly through central mechanisms. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030601
Inverse agonist activity of agouti and agouti-related protein. Peptides 20030401
Modulation of melanocortin-induced changes in spinal nociception by mu-opioid receptor agonist and antagonist in neuropathic rats. Neuroreport 20021220
Estradiol treatment fails to affect the feeding responses to melanocortin-3/4 receptor agonism or antagonism in ovariectomized rats. Peptides 20020901
Activation of central melanocortin pathways by fenfluramine. Science (New York, N.Y.) 20020726
Molecular determinants of human melanocortin-4 receptor responsible for antagonist SHU9119 selective activity. The Journal of biological chemistry 20020607
Hyperleptinemia in A(y)/a mice upregulates arcuate cocaine- and amphetamine-regulated transcript expression. American journal of physiology. Endocrinology and metabolism 20020401
The melanocortin receptor agonist MTII augments the rewarding effect of amphetamine in ad-libitum-fed and food-restricted rats. Psychopharmacology 20020401
Chronic blockade of melanocortin receptors alleviates allodynia in rats with neuropathic pain. Anesthesia and analgesia 20011201
Activation of central melanocortin receptors by MT-II increases cavernosal pressure in rabbits by the neuronal release of NO. British journal of pharmacology 20011201
Central melanocortin receptors regulate insulin action. The Journal of clinical investigation 20011001
Structure activity studies of the melanocortin-4 receptor by in vitro mutagenesis: identification of agouti-related protein (AGRP), melanocortin agonist and synthetic peptide antagonist interaction determinants. Biochemistry 20010522
Hypothalamic, metabolic, and behavioral responses to pharmacological inhibition of CNS melanocortin signaling in rats. The Journal of neuroscience : the official journal of the Society for Neuroscience 20010515
Characterization of melanocortin receptor ligands on cloned brain melanocortin receptors and on grooming behavior in the rat. European journal of pharmacology 19990813
Further pharmacological characterization of the selective melanocortin 4 receptor antagonist HS014: comparison with SHU9119. Neuropeptides 19990601
Properties