Name: (E)-C-HDMAPP (ammonium salt)
Rating: 5 (10 reviews)

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HIT ID:HIT212732673
Cas No:933030-60-5
常用名:(E)-C-HDMAPP (ammonium salt)
IUPAC:triammonium [(3E)-5-hydroxy-4-methylpent-3-en-1-yl](phosphonatooxy)phosphinate
IUPAC:triammonium [(3E)-5-hydroxy-4-methylpent-3-en-1-yl](phosphonatooxy)phosphinate
InChI key:VLHWKNAWRGFXCI-LESCHLGKSA-N

分子式:C6H23N3O7P2
分子量:311.212
氢键供体数 (HBD):1
氢键受体数 (HBA):6
LogP:-1.0635436
SMILES:[NH4+].[NH4+].[NH4+].C\C(CO)=C/CCP([O-])(=O)OP([O-])([O-])=O
SMILES:[NH4+].[NH4+].[NH4+].C\C(CO)=C/CCP([O-])(=O)OP([O-])([O-])=O

Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of γδ-T lymphocytes. Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of γδ-T cells. (E)-C-HDMAPP is the pyrophosphonate form of (E)-HDMAPP. The pyrophosphonate moiety in (E)-C-HDMAPP is much less susceptible to chemical or enzymatic hydrolysis than its pyrophosphate counterpart. As a result, (E)-C-HDMAPP is much more stable in solution and in vascular circulation. (E)-C-HDMAPP possesses comparable activity to (E)-HDMAPP, which is the most potent of the isoprenoid phosphoantigens. (E)-C-HDMAPP stimulates the synthesis of tumor necrosis factor (TNF-α) by γδ-T lymphocytes with an IC50 value of 0.91 nM. (E)-C-HDMAPP also significantly increases the number of circulating γδ-T cells in vivo, in cynomolgus monkeys.

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