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141801-26-5 | L-Phenylalaninamide, L-tyrosyl-L-prolyl-L-phenylalanyl-
CAS No: 141801-26-5 Catalog No: AG001H7A MDL No:
Product Description
Catalog Number:
AG001H7A
Chemical Name:
L-Phenylalaninamide, L-tyrosyl-L-prolyl-L-phenylalanyl-
CAS Number:
141801-26-5
Molecular Formula:
C32H37N5O5
Molecular Weight:
571.6667
IUPAC Name:
(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
InChI:
InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1
InChI Key:
XIJHWXXXIMEHKW-LJWNLINESA-N
SMILES:
Oc1ccc(cc1)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)Cc1ccccc1)N
UNII:
3PH5M0466G
Properties
Complexity:
911
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
571.279g/mol
Formal Charge:
0
Heavy Atom Count:
42
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
5
Isotope Atom Count:
0
Molecular Weight:
571.678g/mol
Monoisotopic Mass:
571.279g/mol
Rotatable Bond Count:
12
Topological Polar Surface Area:
168A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3
Literature
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|---|---|
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| Postnatal development of ectopic sensory fibers containing endomorphin-2 in the white matter of the spinal cord of a transgenic mouse expressing nerve growth factor in oligodendrocytes. | Neuroscience 20050101 |
| Internalization and down-regulation of mu opioid receptors by endomorphins and morphine in SH-SY5Y human neuroblastoma cells. | Brain research 20041203 |
| Depressor and bradycardic responses to microinjections of endomorphin-2 into the NTS are mediated via ionotropic glutamate receptors. | American journal of physiology. Regulatory, integrative and comparative physiology 20041001 |
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| Nonopioidergic mechanism mediating morphine-induced antianalgesia in the mouse spinal cord. | The Journal of pharmacology and experimental therapeutics 20040701 |
| Development of potent bifunctional endomorphin-2 analogues with mixed mu-/delta-opioid agonist and delta-opioid antagonist properties. | Journal of medicinal chemistry 20040701 |
| Differential conditioned place preference responses to endomorphin-1 and endomorphin-2 microinjected into the posterior nucleus accumbens shell and ventral tegmental area in the rat. | The Journal of pharmacology and experimental therapeutics 20040501 |
| Endomorphins exit the brain by a saturable efflux system at the basolateral surface of cerebral endothelial cells. | Experimental brain research 20040501 |
| Co-localization of endomorphin-2 and substance P in primary afferent nociceptors and effects of injury: a light and electron microscopic study in the rat. | The European journal of neuroscience 20040401 |
| Supraspinal anti-allodynic and rewarding effects of endomorphins in rats. | Peptides 20040401 |
| Dynorphinergic mechanism mediating endomorphin-2-induced antianalgesia in the mouse spinal cord. | The Journal of pharmacology and experimental therapeutics 20031201 |
| Lack of mu-opioid receptor-mediated G-protein activation in the spinal cord of mice lacking Exon 1 or Exons 2 and 3 of the MOR-1 gene. | Journal of pharmacological sciences 20031201 |
| Endomorphins, endogenous opioid peptides, provide antioxidant defense in the brain against free radical-induced damage. | Biochimica et biophysica acta 20031120 |
| Effects of endomorphin on substantia gelatinosa neurons in rat spinal cord slices. | British journal of pharmacology 20031101 |
| Intrathecal treatment with 6-hydroxydopamine or 5,7-dihydroxytryptamine blocks the antinociception induced by endomorphin-1 and endomorphin-2 given intracerebroventricularly in the mouse. | Journal of pharmacological sciences 20031101 |
| Degradation of endomorphin-2 at the supraspinal level in mice is initiated by dipeptidyl peptidase IV: an in vitro and in vivo study. | Biochemical pharmacology 20030815 |
| Morphine and endomorphins differentially regulate micro-opioid receptor mRNA in SHSY-5Y human neuroblastoma cells. | The Journal of pharmacology and experimental therapeutics 20030801 |
| Endomorphin-2, deltorphin II and their analogs suppress formalin-induced nociception and c-Fos expression in the rat spinal cord. | Life sciences 20030613 |
| Structural studies of [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond. | Bioorganic & medicinal chemistry 20030501 |
| The antitussive effects of endomorphin-1 and endomorphin-2 in mice. | European journal of pharmacology 20030425 |
| The effect of endomorphins on the release of 3H-norepinephrine from rat nucleus tractus solitarii slices. | Regulatory peptides 20030328 |
| Endomorphin 2 analogues containing Dmp residue as an aromatic amino acid surrogate with high mu-opioid receptor affinity and selectivity. | Bioorganic & medicinal chemistry 20030306 |
| Endomorphin-1 and -2 induce naloxone-precipitated withdrawal syndromes in rats. | Peptides 20030301 |
| Synthesis and evaluation of potential affinity labels derived from endomorphin-2. | The journal of peptide research : official journal of the American Peptide Society 20030201 |
| Loss of mu-opioid receptor-mediated G-protein activation in the pons/medulla of mice lacking the exons 2 and 3 of mu-opioid receptor gene. | Neuroscience letters 20021225 |
| Endomorphin-1 and -2 immunoreactive cells in the hypothalamus are labeled by fluoro-gold injections to the ventral tegmental area. | The Journal of comparative neurology 20021216 |
| Cross-tolerance between the different mu-opioid receptor agonists endomorphin-1, endomorphin-2 and morphine at the spinal level in the rat. | Neuroscience letters 20021213 |
| Endomorphin analogues containing D-Pro2 discriminate different mu-opioid receptor mediated antinociception in mice. | British journal of pharmacology 20021201 |
| Spinal pretreatment with antisense oligodeoxynucleotides against exon-1, -4, or -8 of mu-opioid receptor clone leads to differential loss of spinal endomorphin-1-and endomorphin-2-induced antinociception in the mouse. | The Journal of pharmacology and experimental therapeutics 20021101 |
| Effect of guanidino modification and proline substitution on the in vitro stability and blood-brain barrier permeability of endomorphin II. | Journal of pharmaceutical sciences 20021001 |
| Endomorphins suppress nociception-induced c-Fos and Zif/268 expression in the rat spinal dorsal horn. | European journal of pharmacology 20020906 |
| Endomorphins 1 and 2 inhibit IL-10 and IL-12 production and innate immune functions, and potentiate NF-kappaB DNA binding in THP-1 differentiated to macrophage-like cells. | Scandinavian journal of immunology 20020901 |
| In vitro quantitative study of the degradation of endomorphins. | Peptides 20020901 |
| Anatomical and functional correlation of the endomorphins with mu opioid receptor splice variants. | The European journal of neuroscience 20020901 |
| The antinociceptive properties of endomorphin-1 and endomorphin-2 in the mouse. | Japanese journal of pharmacology 20020701 |
| Differential antinociceptive effects induced by intrathecally-administered endomorphin-1 and endomorphin-2 in mice. | Japanese journal of pharmacology 20020701 |
| Endomorphin-induced motivational effect: differential mechanism of endomorphin-1 and endomorphin-2. | Japanese journal of pharmacology 20020701 |
| Differential mechanism of G-protein activation induced by endogenous mu-opioid peptides, endomorphin and beta-endorphin. | Japanese journal of pharmacology 20020701 |
| Endomorphins 1 and 2 induce amnesia via selective modulation of dopamine receptors in mice. | European journal of pharmacology 20020620 |
| Opioid peptides endomorphin-1 and endomorphin-2 in the immune system in humans and in a rodent model of inflammation. | Annals of the New York Academy of Sciences 20020601 |
| Differential antagonism of endomorphin-1 and endomorphin-2 supraspinal antinociception by naloxonazine and 3-methylnaltrexone. | Peptides 20020501 |
| Endomorphins, Met-enkephalin, Tyr-MIF-1, and the P-glycoprotein efflux system. | Drug metabolism and disposition: the biological fate of chemicals 20020301 |
| Responses to microinjections of endomorphin and nociceptin into the medullary cardiovascular areas. | Clinical and experimental pharmacology & physiology 20020301 |
| Involvement of mu(1)-opioid receptors and cholinergic neurotransmission in the endomorphins-induced impairment of passive avoidance learning in mice. | Behavioural brain research 20020201 |
| Activation of mu-opioid receptors inhibits lordosis behavior in estrogen and progesterone-primed female rats. | Hormones and behavior 20020201 |
| Endomorphins inhibit contractile responses of rat thoracic aorta rings induced by phenylephrine and angiotensin II in vitro. | Acta pharmacologica Sinica 20020101 |
| Endomorphin-2 inhibits GABAergic inputs to cardiac parasympathetic neurons in the nucleus ambiguus. | Neuroscience 20020101 |
| Release of [Met5]enkephalin from the spinal cord by intraventricularly administered endomorphin-2, but not endomorphin-1 in the anesthetized rat. | Neuroscience letters 20011204 |
| Endomorphin-1 improves scopolamine-induced impairment of short-term memory via mu1-opioid receptor in mice. | Neuroreport 20011204 |
| Acute antinociceptive tolerance and asymmetric cross-tolerance between endomorphin-1 and endomorphin-2 given intracerebroventricularly in the mouse. | The Journal of pharmacology and experimental therapeutics 20011201 |
| Pseudoproline-containing analogues of morphiceptin and endomorphin-2: evidence for a cis Tyr-Pro amide bond in the bioactive conformation. | Journal of medicinal chemistry 20011108 |
| Conformational comparison of mu-selective endomorphin-2 with its C-terminal free acid in DMSO solution, by 1H NMR spectroscopy and molecular modeling calculation. | The journal of peptide research : official journal of the American Peptide Society 20011101 |
| Up-regulation of spinal mu-opioid receptor function to activate G-protein by chronic naloxone treatment. | Brain research 20010921 |
| Differential antinociceptive effects induced by intrathecally administered endomorphin-1 and endomorphin-2 in the mouse. | European journal of pharmacology 20010921 |
| Changes in brain content of nociceptin/orphanin FQ and endomorphin 2 in a rat model of neuropathic pain. | Neuroscience letters 20010921 |
| Partial agonistic action of endomorphins in the mouse spinal cord. | Neuroscience letters 20010907 |
| Endomorphins 1 and 2 modulate chemotaxis, phagocytosis and superoxide anion production by microglia. | Journal of neuroimmunology 20010903 |
| Behavioral and neuroendocrine actions of endomorphin-2. | Peptides 20010901 |
| Differential antinociception induced by spinally administered endomorphin-1 and endomorphin-2 in the mouse. | The Journal of pharmacology and experimental therapeutics 20010801 |
| Effects of loperamide and other opioid-related substances on the transcriptional regulation of the rat pro-opiomelanocortin gene in AtT20 cells. | Neuroendocrinology 20010801 |
| Lack of the involvement of mu1-opioid receptor subtype on motivational effects induced by the endogenous mu-opioid receptor ligands endomorphin-1 and -2 in the mouse. | Neuroscience letters 20010727 |
| Saturable brain-to-blood transport of endomorphins. | Experimental brain research 20010701 |
| Endomorphins 1 and 2, endogenous mu-opioid receptor agonists, impair passive avoidance learning in mice. | European journal of pharmacology 20010608 |
| Involvement of spinal protein kinase Cgamma in the attenuation of opioid mu-receptor-mediated G-protein activation after chronic intrathecal administration of [D-Ala2,N-MePhe4,Gly-Ol(5)]enkephalin. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20010601 |
| Receptor constants for endomorphin-1 and endomorphin-1-ol indicate differences in efficacy and receptor occupancy. | European journal of pharmacology 20010601 |
| Endomorphins and activation of the hypothalamo-pituitary-adrenal axis. | The Journal of endocrinology 20010401 |
| Role of cholecystokinin in the reduction of endomorphin-2-induced antinociception in diabetic mice. | European journal of pharmacology 20010323 |
| Differential effects of endomorphin-1 and -2 on amphetamine sensitization: neurochemical and behavioral aspects. | Synapse (New York, N.Y.) 20010301 |
| Different motivational effects induced by the endogenous mu-opioid receptor ligands endomorphin-1 and -2 in the mouse. | Neuroscience 20010101 |
| Endomorphin and mu-opioid receptors in mouse brain mediate the analgesic effect induced by 2 Hz but not 100 Hz electroacupuncture stimulation. | Neuroscience letters 20001124 |
| Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine. | American journal of respiratory and critical care medicine 20000901 |
| G protein activation by endomorphins in the mouse periaqueductal gray matter. | Journal of biomedical science 20000101 |
| Endomorphin-1 and endomorphin-2 activate mu-opioid receptors in myenteric neurons of the guinea-pig small intestine. | Naunyn-Schmiedeberg's archives of pharmacology 19981201 |
| Endomorphins fully activate a cloned human mu opioid receptor. | FEBS letters 19981113 |
| A potent and selective endogenous agonist for the mu-opiate receptor. | Nature 19970403 |
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