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Record Information
Version4.0
Creation Date2007-05-22 20:33:23 UTC
Update Date2017-09-27 08:24:42 UTC
HMDB IDHMDB0006268
Secondary Accession Numbers
  • HMDB06268
Metabolite Identification
Common NameN-Acetylneuraminate 9-phosphate
DescriptionN-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29).
Structure
Thumb
SynonymsNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-1139000000-31a61c834ec1e7590647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-6798000000-0e71876811a2de198680View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9360000000-c2de932aecb7f5fddf22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0umj-4494000000-0fa3501a59ff2e606f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9000000000-abb61d928b00d92157c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e6e329e3f59fa84a900View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Amino Sugar MetabolismPw000008Pw000008 greyscalePw000008 simpleMap00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseasePw000510Pw000510 greyscalePw000510 simpleNot Available
Salla Disease/Infantile Sialic Acid Storage DiseasePw000124Pw000124 greyscalePw000124 simpleNot Available
Sialuria or French Type SialuriaPw000123Pw000123 greyscalePw000123 simpleNot Available
Tay-Sachs DiseasePw000215Pw000215 greyscalePw000215 simpleNot Available
Displaying all 5 entries
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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