muramylnac-ala-isogln-lys-tripeptide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

muramylNAc-Ala-isoGln-Lys-tripeptide: Ala-Ala dipeptide is added to this tripeptide by MurF synthetase to make the peptidoglycan pentapeptide; often called muramyl tripeptide but that term is ambiguous, confused with other tripeptides of muramic acid; the phosphatidylethanolamine conjugate is sometimes used [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	119512
MeSH ID	M0107764

Synonyms (14)

Synonym
murnac-tripeptide
64374-58-9
2-[[4-[2-[2-(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxypropanoylamino]propanoylamino]-5-amino-5-oxopentanoyl]amino]-6-aminoheptanedioic acid
acmu-ala-iso-gln-2,2'-diaminopimelic acid
dl-lysine, n2-(n2-(n-(n-acetylmuramoyl)-l-alanyl)-d-alpha-glutaminyl)-6-carboxy-, erythro-
lysine, n-(n-acetylmuramoyl)-l-alanyl-d-alpha-glutaminyl-6-carboxy-, erythro-
ac-mur-l-ala-gamma-d-gln-meso-a(2)pm
n-(n-acetylmuramoyl)-l-alanyl-d-alpha-glutaminyl-6-carboxylysine,
n-acetylmuramyl-alanyl-isoglutaminyl-meso-2,2'-diaminopimelic acid
d-glutamine, n2-(n-(n-acetylmuramoyl)-l-alanyl)-n-(5-amino-1,5-dicarboxypentyl)-, (r,s)-
n-acetylmuramyl-l-alanyl-d-isoglutaminyl-l-lysine
muramylnac-ala-isogln-lys-tripeptide
DTXSID50982928
3-o-(1-{[1-({5-[(5-amino-1,5-dicarboxypentyl)imino]-1,5-dihydroxy-1-iminopentan-2-yl}imino)-1-hydroxypropan-2-yl]imino}-1-hydroxypropan-2-yl)-2-deoxy-2-[(1-hydroxyethylidene)amino]hexose

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" A definite species variation was established with regard to the toxic nature of muramyl peptides."	( Species variability for toxicity of free and liposome-encapsulated muramyl peptides administered intravenously. Brown, NO; Fidler, IJ; Hart, IR, 1985)	0.27

Compound-Compound Interactions

Excerpt	Reference	Relevance
" The purpose of this study was 2-fold: (a) to determine whether doxorubicin (DOX) would enhance or interfere with the effect of muramyl dipeptide and lipopolysaccharide on canine monocyte activation as measured by an in vitro WEHI-164 cell cytotoxicity assay; and (b) to evaluate the in vivo effect of DOX alone and combined with liposome-encapsulated muramyl tripeptide-phosphatidylethanolamine (L-MTP-PE) on monocyte activation and serum tumor necrosis factor activity."	( In vitro and in vivo effect of doxorubicin combined with liposome-encapsulated muramyl tripeptide on canine monocyte activation. Kurzman, ID; MacEwen, EG; Shi, F, 1993)	0.29

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (47)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	18 (38.30)	18.7374
1990's	20 (42.55)	18.2507
2000's	8 (17.02)	29.6817
2010's	1 (2.13)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.14

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	10.14 (24.57)
Research Supply Index	4.01 (2.92)
Research Growth Index	4.14 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (10.14)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	4 (8.00%)	5.53%
Reviews	2 (4.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	44 (88.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
glycine [no description available]	2.02	1	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
ifosfamide [no description available]	5.76	2	2	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.71	3	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	1.97	1	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
clodronic acid Clodronic Acid: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification.. clodronic acid : An organochlorine compound that is methylene chloride in which both hydrogens are replaced by phosphonic acid groups. It inhibits bone resorption and soft tissue calcification, and is used (often as the disodium salt tetrahydrate) as an adjunct in the treatment of severe hypercalcaemia associated with malignancy, and in the management of osteolytic lesions and bone pain associated with skeletal metastases.	1.99	1	0	1,1-bis(phosphonic acid); one-carbon compound; organochlorine compound	antineoplastic agent; bone density conservation agent
ribavirin Rebetron: Rebetron is tradename	1.97	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	1.96	1	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
1,2-dipalmitoyl-3-phosphatidylethanolamine 1,2-dipalmitoyl-3-phosphatidylethanolamine: RN given refers to parent cpd without isomeric designation	1.97	1	0
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	3.26	6	0
methotrexate [no description available]	5.76	2	2	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
cortisone [no description available]	1.98	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
diaminopimelic acid Diaminopimelic Acid: A diamino derivative of heptanedioic acid with amino groups at C-2 and C-6 and the general formula (COOH)CH(NH2)CH2CH2CH2CH(NH2)(COOH).. LL-2,6-diaminopimelic acid : A 2,6-diaminopimelic acid in which both chiral centres have S configuration. It is a component of bacterial cell wall.	2.71	3	0	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
udp-n-acetylmuramic acid pentapeptide [no description available]	1.97	1	0
asialo gm1 ganglioside [no description available]	1.97	1	0
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	1.97	1	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
uridine diphosphate n-acetylmuramic acid Uridine Diphosphate N-Acetylmuramic Acid: A nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed.. UDP-N-acetyl-alpha-D-muramate(3-) : A UDP-N-acetyl-D-muramate(3-) in which the anomeric centre of the pyranose fragment has alpha-configuration.	2.39	2	0	UDP-N-acetylmuramate(3-)
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.03	1	0
lipoteichoic acid lipoteichoic acid: lipopolysaccharides with an acyl group anchored to the cell membrane of gram-positive bacteria; functions as an adhesion molecule to facilitate the binding of bacteria to cells, colonization, and invasion; interacts with CD14 to induce NF-κB activation and inflammatory cytokine production; can function as surface antigen; inhibits remineraliztion of artificial lesions and surface-softened enamels;. lipoteichoic acid : A teichoic acid which is covalently bound to a lipid.	2.02	1	0

Condition	Relationship Strength	Studies	Trials
Bone Cancer [description not available]	7.97	6	5
Osteogenic Sarcoma [description not available]	8.28	7	6
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	7.97	6	5
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	8.28	7	6
Colitis, Granulomatous [description not available]	2.43	2	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	2.43	2	0
Polyarthritis [description not available]	2.04	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.4	2	0
Granulomas [description not available]	2.04	1	0
Arthritis Acute or chronic inflammation of JOINTS.	2.04	1	0
Dermatitis Any inflammation of the skin.	2.04	1	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	2.04	1	0
Uveitis Inflammation of part or all of the uvea, the middle (vascular) tunic of the eye, and commonly involving the other tunics (sclera and cornea, and the retina). (Dorland, 27th ed)	2.04	1	0
Malignant Melanoma [description not available]	5.37	5	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	5.37	5	1
Carcinoma, Anaplastic [description not available]	2.88	1	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.88	1	0
Infections, Klebsiella [description not available]	1.96	1	0
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	1.96	1	0
Delayed Hypersensitivity [description not available]	1.98	1	0
Innate Inflammatory Response [description not available]	1.98	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	1.98	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.98	1	0
Cancer of Skin [description not available]	2.38	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.38	2	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.66	3	0
Adenocarcinoma Of Kidney [description not available]	1.98	1	0
Cancer of Kidney [description not available]	1.98	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	1.98	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	1.98	1	0
Cancer of Lung [description not available]	4.28	4	1
Lung Neoplasms Tumors or cancer of the LUNG.	4.28	4	1
Canine Diseases [description not available]	4.34	2	2
Cancer of Mouth [description not available]	3.38	1	1
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.38	1	1
Benign Neoplasms [description not available]	2.89	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.89	1	0
Blood Poisoning [description not available]	1.97	1	0
Infections, Pneumococcal [description not available]	2.38	2	0
Pneumococcal Infections Infections with bacteria of the species STREPTOCOCCUS PNEUMONIAE.	2.38	2	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	1.97	1	0
Bacterial Disease [description not available]	1.97	1	0
Leukocytopenia [description not available]	1.97	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	1.97	1	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	1.97	1	0
Grippe [description not available]	1.97	1	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	1.97	1	0
Experimental Neoplasms [description not available]	2.37	2	0
Plasma Cell Tumor [description not available]	1.96	1	0
Plasmacytoma Any discrete, presumably solitary, mass of neoplastic PLASMA CELLS either in BONE MARROW or various extramedullary sites.	1.96	1	0
Peritoneal Carcinomatosis [description not available]	1.97	1	0
EHS Tumor [description not available]	1.97	1	0
Abdominal Neoplasms New abnormal growth of tissue in the ABDOMEN.	1.97	1	0
Neoplasm Seeding The local implantation of tumor cells by contamination of instruments and surgical equipment during and after surgical resection, resulting in local growth of the cells and tumor formation.	1.97	1	0
Peritoneal Neoplasms Tumors or cancer of the PERITONEUM.	1.97	1	0
Herpes Simplex Virus Infection [description not available]	1.97	1	0
Infections, Orthomyxoviridae [description not available]	1.97	1	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	1.97	1	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	1.97	1	0
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	1.97	1	0
Cancer, Radiation-Induced [description not available]	1.96	1	0
Germinoblastoma [description not available]	1.96	1	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.96	1	0

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