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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-05-22 20:33:23 UTC
Update Date2020-02-26 21:26:18 UTC
HMDB IDHMDB0006268
Secondary Accession Numbers
  • HMDB06268
Metabolite Identification
Common NameN-Acetylneuraminate 9-phosphate
DescriptionN-Acetylneuraminate 9-phosphate belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetylneuraminate 9-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, N-acetylneuraminate 9-phosphate participates in a number of enzymatic reactions. In particular, N-acetylneuraminate 9-phosphate can be biosynthesized from N-acetyl-D-mannosamine 6-phosphate and phosphoenolpyruvic acid through the action of the enzyme sialic acid synthase. In addition, N-acetylneuraminate 9-phosphate can be converted into N-acetylneuraminic acid; which is mediated by the enzyme N-acylneuraminate-9-phosphatase. In humans, N-acetylneuraminate 9-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway.
Structure
Data?1582752378
Synonyms
ValueSource
N-Acetylneuraminic acid 9-phosphoric acidGenerator
Chemical FormulaC11H20NO12P
Average Molecular Weight389.2498
Monoisotopic Molecular Weight389.072311621
IUPAC Name(4R,5S,6S)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
Traditional Name(4R,5S,6S)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=O)N[C@H]1[C@H](O)CC(O)(O[C@@H]1[C@H](O)[C@H](O)COP(O)(O)=O)C(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?/m1/s1
InChI KeySQMNIXJSBCSNCI-KHLKYKDFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • 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
  • Carboxamide group
  • Secondary alcohol
  • 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 DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP-2.6ALOGPS
logP-3.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area223.31 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.65 m³·mol⁻¹ChemAxon
Polarizability32.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9743000000-b73738966b1be90e21d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03di-9540238000-9bc6425495a2d9e98f2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-1139000000-31a61c834ec1e7590647Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-6798000000-0e71876811a2de198680Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9360000000-c2de932aecb7f5fddf22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0umj-4494000000-0fa3501a59ff2e606f0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9000000000-abb61d928b00d92157c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e6e329e3f59fa84a900Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023867
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06241
BioCyc IDNot Available
BiGG ID47736
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477814
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
NANP
Uniprot ID:
Q8TBE9
Molecular weight:
27812.875