Basic information
- CAS
24967-27-9- Standard SMILES
CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1O- InChIKey
JINJZWSZQKHCIP-UFGQHTETSA-N- Molecular formula
- C11H17NO8
- Average molar mass
- 291.25 g/mol
- Monoisotopic mass
- 291.0954165
Overview
2-deoxy-2,3-dehydro-N-acetylneuraminic acid is N-Acetylneuraminic acid reduced across the 2,3-bond with loss of the hydroxy group at C-2; it is a minor component of body fluids although abundant in sialuria. It is a conjugate acid of a 2-deoxy-2,3-dehydro-N-acetylneuraminate.
Names & identifiers
- Preferred name
- 5-N-Acetyl-2-deoxy-2,3-didehydro-neuraminic acid
- IUPAC
- (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
- English name
- N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT
- Molecular formula
- C11H17NO8
- Molecular weight
- 291.25
Names & synonyms
Neu2en5Ac5-N-Acetyl-2-deoxy-2,3-didehydro-neuraminic acidSNFG:Neu2en5AcNeu2en5Ac (SNFG)RefChem:111343624967-27-9Neu5Ac2en2-Deoxy-2,3-dehydro-N-acetylneuraminic acidN-Acetyl-2,3-dehydro-2-deoxyneuraminic acid2,3-Dehydro-2-deoxy-N-acetylneuraminic acidN-Acetyl-2,3-didehydro-2-deoxyneuraminic acid1,3-Dehydro-2-deoxy-N-acetylneuraminicacid
Show more names
N-ACETYL-2 3-DEHYDRO-2-DEOXYNEURAMINIC &2-deoxy-2,3-dehydro-n-acetylneuraminicacid1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid DANAN-Acetyl-2,3-didehydro-2-deoxyneuraminic Acid >N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid >=93%
D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acidMFCD001358102-deoxy-2,3-dehydro-n-acetyl-neuraminic acidCHEMBL96712QR7675ZK8XCHEBI:280622,3-didehydro-2-deoxy-N-acetylneuraminic acid
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 157 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 409
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 227 · 227-228
- Boiling point
- 773.4 · 773.4±60.0 °C(Predicted)
- Density
- 1.58 · 1.58±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 2 O: · H2O: soluble50mg/mL, clear, colorless
- pka
- 3.9 · 3.90±0.70(Predicted)
- form
- Solid
- color
- White to Pale Yellow
- biological source
- synthetic (organic)
- optical activity
- 20 · [α]20/D 40.8 to 51.0 °, c =0.66% (w/v) in water
- Water Solubility
- 1 mM · water: 1mM
- BRN
- 8722455 · 8722455
- InChI
- 1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesNeuraminidase (sialidase) inhibitor
UsesN-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is a bacterial, viral, and mammalian neuraminidase inhibitor. It can be used in biological study of knockdown of Neu4 and injection of sialidase inhibitor such as DANA resulted in impairment of long-term potentiation at mossy fiber-CA3 synapses and hippocampus-dependent spatial memory in rats.
Suppliers35 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
上海凯森斯生物科技有限公司18616988519 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
Aladdin Scientific[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
Related reactions
0 records
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Compound notes
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