Synonym
504; PHAD®-504; Monophosphoryl Lipid A-504; PHAD-504; PHAD 504; PHAD504;
IUPAC/Chemical Name
ammonium (2R,3S,4R,5R,6R)-6-(((2R,3S,4R,5R,6S)-3,6-dihydroxy-5-((R)-3-hydroxytetradecanamido)-4-(((R)-3-hydroxytetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-((R)-3-(dodecanoyloxy)tetradecanamido)-2-(hydroxymethyl)-4-(((R)-3-(tetradecanoyloxy)tetradecanoyl)oxy)tetrahydro-2H-pyran-3-yl hydrogen phosphate
InChi Key
CYRPJUBABDDIFR-ADEWMWGLSA-N
InChi Code
InChI=1S/C94H177N2O22P.H3N/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)113-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)117-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)112-83(102)67-61-55-49-43-36-30-24-18-12-6)94(115-79(73-97)90(92)118-119(108,109)110)111-74-80-89(106)91(116-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(93(107)114-80)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2;/h75-80,87-94,97-99,106-107H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,108,109,110);1H3/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93+,94-;/m1./s1
SMILES Code
O[C@H]([C@@H](CO[C@@H]([C@@H]1NC(C[C@H](OC(CCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](CO)[C@@H](OP([O-])(O)=O)[C@@H]1OC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](O)[C@@H]2NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H]2OC(C[C@H](O)CCCCCCCCCCC)=O.[NH4+]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
PHAD®-504 was designed as a synthetic structural analog of detoxified MPLA derived from E. coli lipopolysaccharide (LPS). It is structurally similar to PHAD®, differing only in the length of a single fatty acid chain.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,735.45
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1. Ji Y, An J, Hwang D, Ha DH, Lim SM, Lee C, Zhao J, Song HK, Yang EG, Zhou P, Chung HS. Metabolic engineering of Escherichia coli to produce a monophosphoryl lipid A adjuvant. Metab Eng. 2020 Jan;57:193-202. doi: 10.1016/j.ymben.2019.11.009. Epub 2019 Nov 28. PMID: 31786244; PMCID: PMC6960009.
Huang, W. C., Deng, B., Seffouh, A., Ortega, J., Long, C. A., Suresh, R. V., ... & Lovell, J. F. (2020). Antibody response of a particle-inducing, liposome vaccine adjuvant admixed with a Pfs230 fragment. npj Vaccines, 5(1), 23.
Mabrouk, M. T., Huang, W. C., Miura, K., Li-Purcell, N., Atilla-Gokcumen, G. E., Seffouh, A., ... & Lovell, J. A cobalt porphyrin liposomal adjuvant with reduced MPLA, capability for lyophilization and re-constitution, and thermostability.
