Home Other Building Blocks N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1

N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1

CAS No.:
164204-38-0
Catalog Number:
AG00ASSA
Molecular Formula:
C23H34N3Na2O10P
Molecular Weight:
589.4835
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$153
- +
5mg
≥98%
1 week
United States
$248
- +
10mg
≥98%
1 week
United States
$393
- +
25mg
≥98%
1 week
United States
$776
- +
Product Description
Catalog Number:
AG00ASSA
Chemical Name:
N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1
CAS Number:
164204-38-0
Molecular Formula:
C23H34N3Na2O10P
Molecular Weight:
589.4835
MDL Number:
MFCD01459907
IUPAC Name:
disodium;(2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[[oxido-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]pentanoyl]amino]propanoate
InChI:
InChI=1S/C23H34N3O10P.2Na/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15;;/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34);;/q;2*+1/p-2/t12-,16-,17-,18-,19+,20+,23-;;/m0../s1
InChI Key:
OQKHVXFOYFBMDJ-ODIUWQMJSA-L
SMILES:
CC(C[C@@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)NP(=O)(O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)C.[Na].[Na]
UNII:
3F7O684NXF
Properties
Complexity:
834  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
0
Exact Mass:
587.162g/mol
Formal Charge:
0
Heavy Atom Count:
39  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
587.473g/mol
Monoisotopic Mass:
587.162g/mol
Rotatable Bond Count:
10  
Topological Polar Surface Area:
216A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Neurogenic airway microvascular leakage induced by toluene inhalation in rats. European journal of pharmacology 20120615
In-silico characterization of ECE-1 inhibitors. Computers in biology and medicine 20120401
Antinociceptive effect of [Met5]enkephalin semicarbazide is not affected by dipeptidyl carboxypeptidase-I. Journal of peptide science : an official publication of the European Peptide Society 20120201
The role of neutral endopeptidase in caerulein-induced acute pancreatitis. Journal of immunology (Baltimore, Md. : 1950) 20111115
Aβ-degrading enzymes: potential for treatment of Alzheimer disease. Journal of neuropathology and experimental neurology 20111101
Crystal structure of Mycobacterium tuberculosis zinc-dependent metalloprotease-1 (Zmp1), a metalloprotease involved in pathogenicity. The Journal of biological chemistry 20110916
Dendroaspis natriuretic peptide and the designer natriuretic peptide, CD-NP, are resistant to proteolytic inactivation. Journal of molecular and cellular cardiology 20110701
Cysteine cathepsins in human carious dentin. Journal of dental research 20110401
Intranasal phosphoramidon increases beta-amyloid levels in wild-type and NEP/NEP2-deficient mice. Journal of molecular neuroscience : MN 20110301
Endothelin-1 expression by vascular endothelial growth factor in human umbilical vein endothelial cells and aortic smooth muscle cells. Hypertension in pregnancy 20110101
Neprilysin-2 is an important β-amyloid degrading enzyme. The American journal of pathology 20110101
Bradykinin-induced lung inflammation and bronchoconstriction: role in parainfluenze-3 virus-induced inflammation and airway hyperreactivity. The Journal of pharmacology and experimental therapeutics 20101201
Increased endothelial exocytosis and generation of endothelin-1 contributes to constriction of aged arteries. Circulation research 20100723
Production of an antigenic peptide by insulin-degrading enzyme. Nature immunology 20100501
Diabetes-associated changes and role of N epsilon-(carboxymethyl)lysine in big ET-1-induced coronary vasoconstriction. Peptides 20100201
Positron emission tomography of [18F]-big endothelin-1 reveals renal excretion but tissue-specific conversion to [18F]-endothelin-1 in lung and liver. British journal of pharmacology 20100201
Intrathecal substance P augments morphine-induced antinociception: possible relevance in the production of substance P N-terminal fragments. Peptides 20090901
Neutral endopeptidase inhibition enhances substance P mediated inflammation due to hypomagnesemia. Magnesium research 20090901
Functional and molecular characterization of the endothelin system in retinal arterioles. Investigative ophthalmology & visual science 20090701
Structure of human endothelin-converting enzyme I complexed with phosphoramidon. Journal of molecular biology 20090109
[Changes in the activity of amyloid-degrading metallopeptidases leads to disruption of memory in rats]. Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova 20090101
Role of endogenous endothelin-1 in post-ischemic cardiac dysfunction and norepinephrine overflow in rat hearts. European journal of pharmacology 20080904
Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2. Journal of medicinal chemistry 20080626
Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury. Experimental lung research 20080301
Great increase in antinociceptive potency of [Leu5]enkephalin after peptidase inhibition. Journal of pharmacological sciences 20080201
Effects of endothelin-1 1-31 on cell viabililty and [Ca2+]i in cultured neonatal rat cardiomyocytes. Physiological research 20080101
Activation of the amyloid cascade by intracerebroventricular injection of the protease inhibitor phosphoramidon. Neuro-degenerative diseases 20080101
Metabolic inactivation of the circadian transmitter, pigment dispersing factor (PDF), by neprilysin-like peptidases in Drosophila. The Journal of experimental biology 20071201
Characterisation of endothelin converting enzyme-1 shedding from endothelial cells. FEBS letters 20070918
The enhancing effects of peptidase inhibitors on the antinociceptive action of [Met5]enkephalin-Arg6-Phe7 in rats. Journal of pharmacological sciences 20070901
Potentiation of bradykinin effect by angiotensin-converting enzyme inhibition does not correlate with angiotensin-converting enzyme activity in the rat mesenteric arteries. Hypertension (Dallas, Tex. : 1979) 20070701
Functional evidence of des-Arg10-kallidin enzymatic inactivating pathway in isolated human umbilical vein. Naunyn-Schmiedeberg's archives of pharmacology 20070501
Antagonism of phosphoramidon-induced antinociception in mice by mu- but not kappa-opioid receptor blockers. Life sciences 20070417
Effect of chronic ethanol consumption on endothelin-1 generation and conversion of exogenous big-endothelin-1 by the rat carotid artery. Alcohol (Fayetteville, N.Y.) 20070301
Neutral endopeptidase up-regulation in isolated human umbilical artery: involvement in desensitization of bradykinin-induced vasoconstrictor effects. The Journal of pharmacology and experimental therapeutics 20070201
Expression of NEP2, a soluble neprilysin-like endopeptidase, during embryogenesis in Drosophila melanogaster. Peptides 20070101
Inhibition of neutral endopeptidase by thiorphan does not modify coronary vascular responses to angiotensin I, angiotensin II and bradykinin in the isolated guinea pig heart. Pharmacological reports : PR 20070101
Big ET-1 processing into vasoactive peptides in arteries and veins. Vascular pharmacology 20070101
Neprilysin protects human neuronal progenitor cells against impaired development caused by amyloid-beta peptide. Brain research 20061208
Preparation of a protected phosphoramidon precursor via an H-phosphonate coupling strategy. Bioorganic & medicinal chemistry letters 20061101
Effects of big endothelin-1 in comparison with endothelin-1 on the microvascular blood flow velocity and diameter of rat mesentery in vivo. Microvascular research 20061101
Arrhythmogenic action of endothelin-1(1-31) through conversion to endothelin-1(1-21). Experimental biology and medicine (Maywood, N.J.) 20060601
Angiotensin converting enzyme has an inhibitory role in CGRP metabolism in human skin. Peptides 20060401
Phosphodiesterase IV and neutral endopeptidase in airways from developing and allergen sensitized rabbits. Pulmonary pharmacology & therapeutics 20060101
Blood pressure responses of endothelin-1 1-31 within the rostral ventrolateral medulla through conversion to endothelin-1 1-21. Journal of cardiovascular pharmacology 20051201
Role of endothelin-1-dependent up-regulation of leptin in oral mucosal repair. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20051201
Endothelin-1-dependent leptin induction in gastric mucosal inflammatory responses to Helicobacter pylori lipopolysaccharide. Biochemical and biophysical research communications 20051104
NEP inhibitors enhance C-type natriuretic peptide-induced relaxation in porcine isolated coronary artery. Vascular pharmacology 20051001
Inhibition of neutral endopeptidase (NEP) facilitates neurogenic inflammation. Experimental neurology 20050901
Endothelin-1 (1-31) is an intermediate in the production of endothelin-1 after big endothelin-1 administration in vivo. Hypertension (Dallas, Tex. : 1979) 20050701
Contribution of endogenous endothelin-1 to basal vascular tone during normal pregnancy and preeclampsia. American journal of obstetrics and gynecology 20050701
The role of substance P and bradykinin in the cough reflex and bronchoconstriction in guinea-pigs. European journal of pharmacology 20050418
Purification, characterization cloning, and sequencing of metalloendopeptidase from Streptomyces septatus TH-2. Archives of biochemistry and biophysics 20050215
Down-regulation does not mediate natriuretic peptide-dependent desensitization of natriuretic peptide receptor (NPR)-A or NPR-B: guanylyl cyclase-linked natriuretic peptide receptors do not internalize. Molecular pharmacology 20050101
Effective antiprotease-antibiotic treatment of experimental anthrax. BMC infectious diseases 20050101
Further evidence on the anxiogenic-like effect of substance P evaluated in the elevated plus-maze in rats. Behavioural brain research 20041005
Despite minimal hemodynamic alterations endotoxemia modulates NOS and p38-MAPK phosphorylation via metalloendopeptidases. Molecular and cellular biochemistry 20041001
[Physiological and pathophysiological roles of the endothelin converting enzymes]. Nihon rinsho. Japanese journal of clinical medicine 20040901
Hypoxia augments TNF-alpha-mediated endothelin-1 release and cell proliferation in human optic nerve head astrocytes. Biochemical and biophysical research communications 20040604
Endothelin-induced constriction of the ductus venosus in fetal sheep: developmental aspects and possible interaction with vasodilatory prostaglandin. British journal of pharmacology 20040601
[Endothelin]. Nihon rinsho. Japanese journal of clinical medicine 20040601
A continuous spectrophotometric assay for Pseudomonas aeruginosa LasA protease (staphylolysin) using a two-stage enzymatic reaction. Analytical biochemistry 20040515
The effect of phosphoramidon on inflammation-mediated preterm delivery in a mouse model. American journal of obstetrics and gynecology 20040201
Signal pathway involved in increased expression of neutral endopeptidase 24.11 by gonadotropin releasing hormone in choriocarcinoma cells. Placenta 20040101
[The new class of drugs-- metalloprotease inhibitors -- in the treatment of heart failure]. Klinicheskaia meditsina 20040101
A low dose of angiotensin II increases inotropism through activation of reverse Na(+)/Ca(2+) exchange by endothelin release. Cardiovascular research 20031201
[Protective effects of phosphoramidon on the experimental myocardial injury in rats]. Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 20031201
Active amino acids of the Kell blood group protein and model of the ectodomain based on the structure of neutral endopeptidase 24.11. Blood 20031015
Metalloendopeptidase inhibition regulates phosphorylation of p38-mitogen-activated protein kinase and nitric oxide synthase in heart after endotoxemia. Shock (Augusta, Ga.) 20031001
The role of endothelin converting enzyme inhibition during group B streptococcus-induced pulmonary hypertension in newborn piglets. Pediatric research 20030901
Cerebral angiogenesis and expression of VEGF after subarachnoid hemorrhage (SAH) in rats. Brain research 20030815
Isolation and characterization of a zinc-containing metalloprotease expressed by Vibrio tubiashii. Canadian journal of microbiology 20030801
The effects of phosphoramidon on the expression of human endothelin-converting enzyme-1 (ECE-1) isoforms. Journal of cardiovascular pharmacology 20030701
[D-Val22]big ET-1[16-38] inhibits endothelin-converting enzyme activity: a promising concept in the prevention of cerebral vasospasm. Neurosurgical review 20030501
Pseudomonas aeruginosa elastase degrades surfactant proteins A and D. American journal of respiratory cell and molecular biology 20030401
Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of protein kinase C constrictor pathway. Neurological research 20030401
Binding of a new bioactive 31-amino-acid endothelin-1 to an endothelin ET(B) or ET(B)-like receptor in porcine lungs. European journal of pharmacology 20030328
Peptidases prevent mu-opioid receptor internalization in dorsal horn neurons by endogenously released opioids. The Journal of neuroscience : the official journal of the Society for Neuroscience 20030301
Effects of kinins on mammalian spermatozoa and the impact of peptidolytic enzymes. Andrologia 20030201
Effect of endothelin-1 (1-31) on the renal resistance vessels. The journal of medical investigation : JMI 20030201
Role of tachykinins in the bronchoconstriction induced by HCl intraesophageal instillation in the rabbit. Life sciences 20030124
Action of three ectopeptidases on corticotropin-releasing factor: metabolism and functional aspects. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030101
Attenuation of renal ischemia/reperfusion injury by a triple drug combination therapy. Journal of nephrology 20030101
Cardioprotective effects of phosphoramidon on myocardial structure and function in murine Chagas' disease. International journal for parasitology 20021101
The mechanisms for tachykinin-induced contractions of the rabbit corpus cavernosum. British journal of pharmacology 20021101
Effect of endothelin-converting enzyme inhibitors on big endothelin-1 induced contraction in isolated rat basilar artery. Acta neurochirurgica 20021101
Combination therapy of N-acetylcysteine, sodium nitroprusside and phosphoramidon attenuates ischemia-reperfusion injury in rat kidney. Molecular and cellular biochemistry 20021101
Attenuation of ischemia/reperfusion induced MAP kinases by N-acetyl cysteine, sodium nitroprusside and phosphoramidon. Molecular and cellular biochemistry 20021101
The increased proliferation of cultured neuroblastoma cells treated with vasoactive intestinal peptide is enhanced by simultaneous inhibition of neutral endopeptidase. Regulatory peptides 20021015
Effect of quercetin on plasma extravasation in rat CNS and dura mater by ACE and NEP inhibition. Phytotherapy research : PTR 20020901
Endothelin-converting enzyme activity in human cerebral circulation. Neurosurgery 20020801
Characterization of PgPepO, a bacterial homologue of endothelin-converting enzyme-1. Clinical science (London, England : 1979) 20020801
Expression, purification and characterization of the monomeric and dimeric forms of soluble bovine endothelin converting enzyme-1a. Clinical science (London, England : 1979) 20020801
Phosphoramidon treatment improves the consequences of chagasic heart disease in mice. Clinical science (London, England : 1979) 20020801
Pressor and pulmonary responses to ET-1(1-31) in guinea-pigs. British journal of pharmacology 20020701
Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation. Placenta 20020701
Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of Rho kinase constrictor pathway. Neurological research 20020601
Inhibition of endothelin-1 improves survival and vasculopathy in rat cardiac transplants treated with cyclosporine. Transplantation 20020415
Substance P induced preprotachykinin-a mRNA, neutral endopeptidase mRNA and substance P in cultured normal fibroblasts. International archives of allergy and immunology 20020401
Enhancement of neurokinin A-induced smooth muscle contraction in human urinary bladder by mucosal removal and phosphoramidon: relationship to peptidase inhibition. European journal of pharmacology 20020308
Endothelin-1[1-31]: a novel autocrine-paracrine regulator of human adrenal cortex secretion and growth. The Journal of clinical endocrinology and metabolism 20020101
Endothelin-converting enzyme activity in vascular smooth muscle preparations in vitro. Methods in molecular biology (Clifton, N.J.) 20020101
Zinc and Manduca sexta hemocyte functions. Journal of insect science (Online) 20020101
Soluble recombinant neprilysin induces aggrecanase-mediated cleavage of aggrecan in cartilage explant cultures. Archives of biochemistry and biophysics 20011215
The role of substance P release in the lung with esophageal acid. The American journal of medicine 20011203
Effect of neutral endopeptidase inhibitor on bradykinin-induced bronchoconstriction. Life sciences 20011121
In vitro contractile effects of neurokinin receptor blockade in the human ureter. The Journal of urology 20011001
Differential effects of U46619 on renal regional hemodynamics in the rat: involvement of endothelin. The Journal of pharmacology and experimental therapeutics 20011001
Determination of bradykinin in rat urine by coupled-column high pressure liquid chromatography with precolumn derivatization with a water-soluble fluorogenic reagent. Analytical biochemistry 20011001
Roles of mast cells and sensory nerves in cutaneous vascular hyperpermeability and scratching behavior induced by poly-L-arginine in rats. European journal of pharmacology 20010817
A proteinase inhibitor decreases tumor growth in a laparoscopic rat model. Surgical endoscopy 20010801
Deletion of neutral endopeptidase exacerbates intestinal inflammation induced by Clostridium difficile toxin A. American journal of physiology. Gastrointestinal and liver physiology 20010801
Changes in the expression of tachykinin receptors in the rat uterus during the course of pregnancy. Biology of reproduction 20010801
Degradation of the Alzheimer's amyloid beta peptide by endothelin-converting enzyme. The Journal of biological chemistry 20010706
Neprilysin degrades both amyloid beta peptides 1-40 and 1-42 most rapidly and efficiently among thiorphan- and phosphoramidon-sensitive endopeptidases. The Journal of biological chemistry 20010615
Soluble CD44 inhibits melanoma tumor growth by blocking cell surface CD44 binding to hyaluronic acid. Oncogene 20010607
Effect of ECE and NEP inhibition on cigarette smoke-induced cell proliferation in the rat lung. Inhalation toxicology 20010601
Endothelium-dependent relaxation in response to low concentrations of bradykinin is enhanced by phosphoramidon, bosentan and BQ-123 in bovine coronary arteries in vitro. Japanese journal of pharmacology 20010601
The lungs as an anti-inflammatory organ of the body. Critical care medicine 20010501
A three-dimensional model of endothelin-converting enzyme (ECE) based on the X-ray structure of neutral endopeptidase 24.11 (NEP). Protein engineering 20010501
Isoprostaglandin E2 type-III (8-iso-prostaglandin E2) evoked contractions in the human internal mammary artery. Life sciences 20010413
Phosphoramidon-sensitive endothelin-converting enzymes modulate cerebral blood flow and neural damage of hypoxic rats. Neuroscience letters 20010330
Reverse mode of the Na+-Ca2+ exchange after myocardial stretch: underlying mechanism of the slow force response. Circulation research 20010302
Interactions of human matrix metalloproteinase 7 (matrilysin) with the inhibitors thiorphan and R-94138. Journal of biochemistry 20010301
Antinociceptive effect produced by intracerebroventricularly administered dynorphin A is potentiated by p-hydroxymercuribenzoate or phosphoramidon in the mouse formalin test. Brain research 20010209
Neutral endopeptidase terminates substance P-induced inflammation in allergic contact dermatitis. Journal of immunology (Baltimore, Md. : 1950) 20010115
Mitogen-activated protein kinase activity regulation role of angiotensin and endothelin systems in vascular smooth muscle cells. European journal of pharmacology 20010105
Effect of phosphoramidon on brain tissue angiogenesis in the chronic phase of vasospasm after subarachnoid hemorrhage in the rat. Medical science monitor : international medical journal of experimental and clinical research 20010101
Role of endothelin-converting enzyme-1 in the suppression of constitutive nitric oxide synthase in rat gastric mucosal injury by indomethacin. Scandinavian journal of gastroenterology 20001101
Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme. Japanese journal of pharmacology 20000901
Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction. Cardiovascular research 19981201
Influence of several peptidase inhibitors on the pro-inflammatory effects of substance P, capsaicin and collagenase. Naunyn-Schmiedeberg's archives of pharmacology 19961101
In vitro metabolism of an insect neuropeptide by neural membrane preparations from Lymantria dispar. Peptides 19960101
Regulation of N-formyl-methionyl-leucyl-phenylalanine receptor recycling by surface membrane neutral endopeptidase-mediated degradation of ligand. Journal of leukocyte biology 19951001
Brain cathepsin B but not metalloendopeptidases degrade rAPP751 with production of amyloidogenic fragments. Comparison with synthetic peptides emulating beta- and gamma-secretase sites. International journal of peptide and protein research 19950101
Purification and characterization of a neutral zinc endopeptidase secreted by Flavobacterium meningosepticum. Archives of biochemistry and biophysics 19940515
Degradation of bradykinin by neutral endopeptidase (EC 3.4.24.11) in cultured human endothelial cells. European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies 19930501
Jurkat T cells express a functional neutral endopeptidase activity (CALLA) involved in T cell activation. The EMBO journal 19921101
Functional reactivity of different central opioid receptor systems following clomipramine treatments. Pharmacological research 19900101
Neuropeptide-degrading endopeptidase activity of locust (Schistocerca gregaria) synaptic membranes. The Biochemical journal 19881101
Effects of bestatin and phosphoramidon on the hypertensive response to physostigmine in the rat. Fundamental & clinical pharmacology 19870101
Enkephalinase inhibition suppresses naloxone-induced jumping in morphine-dependent mice. Archives internationales de pharmacodynamie et de therapie 19861001
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