| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:36:22 UTC |
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| Update Date | 2020-04-22 15:05:15 UTC |
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| BMDB ID | BMDB0000773 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | N-Acetyl-a-neuraminic acid |
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| Description | N-Acetyl-a-neuraminic acid, also known as alpha-neu5ac or O-sialIC ACID, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetyl-a-neuraminic acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on N-Acetyl-a-neuraminic acid. |
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| Structure | |
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| Synonyms | | Value | Source |
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| alpha-Neu5ac | ChEBI | | O-SIALIC ACID | ChEBI | | WURCS=2.0/1,1,0/[aad21122h-2a_2-6_5*ncc/3=o]/1/ | ChEBI | | a-Neu5ac | Generator | | Α-neu5ac | Generator | | O-SIALate | Generator | | N-Acetyl-a-neuraminate | Generator | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonic acid | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonic acid | HMDB | | 5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonate | HMDB | | 5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonic acid | HMDB | | 5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonate | HMDB | | 5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonic acid | HMDB | | N-Acetyl-a-D-neuraminate | HMDB | | N-Acetyl-a-D-neuraminic acid | HMDB | | N-Acetyl-alpha-delta-neuraminate | HMDB | | N-Acetyl-alpha-delta-neuraminic acid | HMDB | | N-Acetyl-alpha-neuraminate | HMDB | | PolySia | HMDB | | Polysialic acid | HMDB | | N-Acetyl-alpha-neuraminic acid | HMDB | | N-Acetyl-α-neuraminate | HMDB | | N-Acetyl-α-neuraminic acid | HMDB | | Acid, N-acetylneuraminic | HMDB | | Acid, sialic | HMDB | | N Acetylneuraminic acid | HMDB | | N-Acetylneuraminic acid | HMDB | | Sialic acid | HMDB | | N-Acetyl-a-neuraminic acid | Generator |
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| Chemical Formula | C11H19NO9 |
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| Average Molecular Weight | 309.2699 |
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| Monoisotopic Molecular Weight | 309.105981211 |
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| IUPAC Name | (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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| Traditional Name | N-acetylneuraminic acid |
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| CAS Registry Number | 21646-00-4 |
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| SMILES | [H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO |
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| InChI Identifier | InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1 |
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| InChI Key | SQVRNKJHWKZAKO-YRMXFSIDSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | N-acylneuraminic acids |
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| Alternative Parents | |
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| Substituents | - N-acylneuraminic acid
- Neuraminic acid
- C-glucuronide
- C-glycosyl compound
- Glycosyl compound
- Alpha-hydroxy acid
- Pyran
- Hydroxy acid
- Oxane
- Acetamide
- Carboxamide group
- Hemiacetal
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic nitrogen compound
- Organopnictogen compound
- Primary alcohol
- Organic oxide
- Carbonyl group
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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