Monophosphoryl Lipid A (Synthetic)(MPLA) - ≥99% , CAS No.1246298-63-4

CAS: 1246298-63-4 Cat. No.: M130160 Molecular Weight: 1763.47 EC Number: 850-455-1 PubChem CID: 134687617

GRADE & PURITY ≥99%

Synonyms

GLA | GLUCOPYRANOSYL LIPID A AMMONIUM | GLA-SE | MONOPHOSPHORYL LIPID A (SYNTHETIC) AMMONIUM | Monophosphoryl lipid A (synthetic) | GLA (ADJUVANT) AMMONIUM | LAPRETOLIMOD AMMONIUM | HY-130320 | HEXAACYL MONOPHOSPHORYL LIPID A AMMONIUM SALT | A1O9D5VN5D |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

By generating a pathogen-specific immune response before infection, vaccination is recognized as an effective way to prevent infection. Typically, immunization with vaccine antigens alone does not induce a robust or durable immune response - leading to a failure of protective immunity against infection. Therefore, adjuvants are needed to enhance the cellular or humoral immune response after immunization.

Monophosphoryl lipid A (MPLA) is either extracted from bacterial lipid A or by chemical synthesis.
MPLA has been used:
• as a component of cobalt porphyrin-phospholipid (Co-PoP) liposomes for the immunization of mice with membrane proximal external region (MPER) of the gp41 envelope protein 
• as an adjuvant along with dimethyldioctadecylammonium bromide(DDA) for C. muridarum recombinant membrane protein based multi-subunit vaccine
• as toll-like receptor-4 (TLR4) agonist adjuvant for respiratory syncytial virus (RSV) fusion (F) protein FI-RSV vaccine

Specifications

Synonyms

GLA | GLUCOPYRANOSYL LIPID A AMMONIUM | GLA-SE | MONOPHOSPHORYL LIPID A (SYNTHETIC) AMMONIUM | Monophosphoryl lipid A (synthetic) | GLA (ADJUVANT) AMMONIUM | LAPRETOLIMOD AMMONIUM | HY-130320 | HEXAACYL MONOPHOSPHORYL LIPID A AMMONIUM SALT | A1O9D5VN5D |

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Monophosphoryl lipid A (MPLA) is a natural agonist for the toll-like receptor-4 (TLR4). It is useful as an adjuvant in immunization. MPLA is a safe prophylactic agent and has immunotherapeutic applications. MPLA used in vaccination improves B cell and T c

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

AGONIST

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504773176
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773176
• Canonical Smiles: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)NC1C(C(C(OC1OCC2C(C(C(C(O2)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)CO)OP(=O)(O)[O-])OC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC.[NH4+]
• IUPAC Name: azanium;[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6S)-3,6-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxyoxan-2-yl]methoxy]-2-(hydroxymethyl)-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-3-yl] hydrogen phosphate
• InChIKey: UPAZUDUZKTYFBG-HNPUZVNISA-N
• INCHI: 1S/C96H181N2O22P.H3N/c1-7-13-19-25-31-37-39-45-51-57-63-69-85(104)114-79(67-61-55-49-43-35-29-23-17-11-5)73-84(103)98-90-94(119-88(107)74-80(68-62-56-50-44-36-30-24-18-12-6)115-86(105)70-64-58-52-46-40-38-32-26-20-14-8-2)92(120-121(110,111)112)81(75-99)117-96(90)113-76-82-91(108)93(118-87(106)72-78(101)66-60-54-48-42-34-28-22-16-10-4)89(95(109)116-82)97-83(102)71-77(100)65-59-53-47-41-33-27-21-15-9-3;/h77-82,89-96,99-101,108-109H,7-76H2,1-6H3,(H,97,102)(H,98,103)(H2,110,111,112);1H3/t77-,78-,79-,80-,81-,82-,89-,90-,91-,92-,93-,94-,95+,96-;/m1./s1
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O)NC(=O)C[C@@H](CCCCCCCCCCC)O)OC(=O)C[C@@H](CCCCCCCCCCC)O)O)CO)OP(=O)(O)[O-])OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC.[NH4+]
• PubChem CID: 134687617
• Molecular Weight: 1763.47

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Amino sugars
            • Level7 Acylaminosugars

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Amino sugars
• Direct Parent: Acylaminosugars
• Alternative Parents: Saccharolipids N-acyl-alpha-hexosamines Fatty acyl glycosides of mono- and disaccharides Tetracarboxylic acids and derivatives Alkyl glycosides Fatty acid esters Beta hydroxy acids and derivatives Oxanes N-acyl amines Monosaccharides Alkyl phosphates Secondary alcohols Carboxylic acid esters Oxacyclic compounds Carboxylic acid amides Organopnictogen compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Saccharolipid - Acylaminosugar - N-acyl-alpha-hexosamine - Fatty acyl glycoside of mono- or disaccharide - Fatty acyl glycoside - Tetracarboxylic acid or derivatives - Alkyl glycoside - Fatty acid ester - Beta-hydroxy acid - Fatty acyl - Alkyl phosphate - Phosphoric acid ester - Oxane - Organic phosphoric acid derivative - N-acyl-amine - Monosaccharide - Hydroxy acid - Fatty amide - Secondary alcohol - Carboxylic acid ester - Carboxamide group - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organonitrogen compound - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Moisture sensitive
• Molecular Weight: 1763.500 g/mol
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 88
• Exact Mass: 1763.31 Da
• Monoisotopic Mass: 1762.31 Da
• Topological Polar Surface Area: 363.000 Ų
• Heavy Atom Count: 122
• Formal Charge: 0
• Complexity: 2550.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3