CAS 24967-27-9|N-acetyl-2,3-didehydro-2-deoxyneuraminic acid
| Common Name | N-acetyl-2,3-didehydro-2-deoxyneuraminic acid | ||
|---|---|---|---|
| CAS Number | 24967-27-9 | Molecular Weight | 291.25500 |
| Density | 1.58g/cm3 | Boiling Point | 773.4ºC at 760 mmHg |
| Molecular Formula | C11H17NO8 | Melting Point | 227-228ºC |
| MSDS | ChineseUSA | Flash Point | 421.6ºC |
Names
| Name | n-acetylneuraminic acid, 2,3-dehydro-2-deoxy-, sodium salt |
|---|---|
| Synonym | More Synonyms |
BiologicalActivity
| Description | N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity[1][2]. |
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| Related Catalog | Signaling Pathways >>Anti-infection >>Influenza VirusResearch Areas >>Infection |
| In Vitro | N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4]. |
| In Vivo | N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10 mg/kg; i.p.; daily) attenuates pulmonary fibrosis in a mouse model[3]. Animal Model: Mice (Mouse model of pulmonary fibrosis)[3] Dosage: 10 mg/kg Administration: I.p.; daily (starting at day 10 after Bleomycin, and then euthanized at day 21) Result: Inhibition of sialidases starting at day 10 after bleomycin attenuates fibrosis. |
| References | [1]. Magesh S, et al. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorg Med Chem Lett. 2008;18(2):532-537. [2]. Xiao A, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47. [3]. Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8. [4]. Minami A, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion. Sci Rep. 2020;10(1):5198. Published 2020 Mar 23. |
Chemical & Physical Properties
| Density | 1.58g/cm3 |
|---|---|
| Boiling Point | 773.4ºC at 760 mmHg |
| Melting Point | 227-228ºC |
| Molecular Formula | C11H17NO8 |
| Molecular Weight | 291.25500 |
| Flash Point | 421.6ºC |
| Exact Mass | 291.09500 |
| PSA | 156.55000 |
| Vapour Pressure | 1.27E-27mmHg at 25°C |
| Index of Refraction | 1.612 |
| InChIKey | JINJZWSZQKHCIP-UFGQHTETSA-N |
| SMILES | CC(=O)NC1C(O)C=C(C(=O)O)OC1C(O)C(O)CO |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Safety Phrases | 22-24/25 |
| RIDADR | NONH for all modes of transport |
Articles45
More Articles| Chemistry, metabolism, and biological functions of sialic acids. Adv. Carbohydr. Chem. Biochem. 40 , 131, (1982) | |
| Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues. J. Med. Chem. 56(7) , 2948-58, (2013) In the past two decades, human neuraminidases (human sialidases, hNEUs) have been found to be involved in numerous pathways in biology. The development of selective and potent inhibitors of these enzy... | |
| Elastin-derived peptides are new regulators of insulin resistance development in mice. Diabetes 62(11) , 3807-16, (2013) Although it has long been established that the extracellular matrix acts as a mechanical support, its degradation products, which mainly accumulate during aging, have also been demonstrated to play an... |
Synonyms
| 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid |
| 2,3,4-TRIMETHYL-3-PENTANOL |
| 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoic acid |
| N-acetyl-2,3-didehydro-2-deoxyneuraminic acid |
| 1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID |
| 2,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID |
| 2,3-Dehydro-2-deoxy-N-acetylneuraminic AcidDANA |
| MFCD00057470 |
| N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid |
| 2,3-didehydro-2-deoxy-N-acetylneuraminic acid |
| 2-deoxy-2,3-dehydro-n-acetylneuraminicacid |
| EINECS 246-550-7 |
