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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 17:54:52 UTC
Update Date2021-09-14 15:18:17 UTC
HMDB IDHMDB0004381
Secondary Accession Numbers
  • HMDB04381
Metabolite Identification
Common NameN-Acetylneuraminic acid 9-phosphate
DescriptionN-Acetylneuraminic acid 9-phosphate is an intermediate in the synthesis of Acetylneuraminic acid, a process occurring in the cytosolic fraction by the human enzyme N-Acetylneuraminic acid 9-phosphate (Neu5Ac 9-P) synthase, that catalyzes the synthesis of N-Acetylneuraminic acid 9-phosphate, in a reaction by the mechanism of aldol condensation of phosphoenolpyruvate (PEP) with sugar substrates, ManNAc-6-P (N-acetylmannosamine 6-phosphate) or Man-6-P (mannose 6-phosphate). N-Acetylneuraminic acid 9-phosphate is converted to N-Acetylneuraminic acid by the enzyme N-acetylneuraminate-9-phosphate phosphatase. (PMID: 16503877 , 6093772 ).
Structure
Thumb
Synonyms
ValueSource
N-Acetylneuraminate 9-phosphateChEBI
N-Acetylneuraminic acid 9-phosphoric acidGenerator
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid 9-(dihydrogen phosphate)HMDB
N-Acetyl- 9-(dihydrogen phosphate)-neuraminic acidHMDB
N-Acetyl-neuraminic acid-9-phosphateHMDB
Chemical FormulaC11H20NO12P
Average Molecular Weight389.2498
Monoisotopic Molecular Weight389.072311621
IUPAC Name(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
Traditional Name(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
CAS Registry Number37992-17-9
SMILES
[H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C11H20NO12P/c1-4(13)12-7-5(14)2-11(19,10(17)18)24-9(7)8(16)6(15)3-23-25(20,21)22/h5-9,14-16,19H,2-3H2,1H3,(H,12,13)(H,17,18)(H2,20,21,22)/t5-,6+,7+,8+,9+,11?/m0/s1
InChI KeySQMNIXJSBCSNCI-LUWBGTNYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylneuraminate-9-phosphates. These are neuraminic acids carrying an N-acyl substituent, as well as a phosphate group at the O9-position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminate-9-phosphates
Alternative Parents
Substituents
  • N-acylneuraminate-9-phosphate
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Monoalkyl phosphate
  • Alpha-hydroxy acid
  • Organic phosphoric acid derivative
  • Hydroxy acid
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyran
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Hemiacetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.235Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023369
KNApSAcK IDNot Available
Chemspider ID389789
KEGG Compound IDC06241
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440962
PDB IDNot Available
ChEBI ID27438
Food Biomarker OntologyNot Available
VMH IDACNAMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hao J, Vann WF, Hinderlich S, Sundaramoorthy M: Elimination of 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthase activity from human N-acetylneuraminic acid 9-phosphate synthase by a single mutation. Biochem J. 2006 Jul 1;397(1):195-201. [PubMed:16503877 ]
  2. Van Rinsum J, Van Dijk W, Hooghwinkel GJ, Ferwerda W: Subcellular localization and tissue distribution of sialic acid-forming enzymes. N-acetylneuraminate-9-phosphate synthase and N-acetylneuraminate 9-phosphatase. Biochem J. 1984 Oct 15;223(2):323-8. [PubMed:6093772 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:
NANS
Uniprot ID:
Q9NR45
Molecular weight:
40307.26
Reactions
N-Acetylneuraminic acid 9-phosphate + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Phosphoenolpyruvic acid + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
NANP
Uniprot ID:
Q8TBE9
Molecular weight:
27812.875
Reactions
N-Acetylneuraminic acid 9-phosphate + Water → N-Acetylneuraminic acid + Phosphatedetails