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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:58 UTC
HMDB IDHMDB0001121
Secondary Accession Numbers
  • HMDB01121
Metabolite Identification
Common NameN-Acetyl-D-mannosamine 6-phosphate
DescriptionN-Acetyl-D-mannosamine 6-phosphate, also known as N-acetyl-D-mannosamine-6-p or mannac-6-p, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-mannosamine 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-mannosamine 6-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, N-acetyl-D-mannosamine 6-phosphate participates in a number of enzymatic reactions. In particular, N-acetyl-D-mannosamine 6-phosphate can be biosynthesized from N-acetylmannosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In addition, N-acetyl-D-mannosamine 6-phosphate and phosphoenolpyruvic acid can be converted into N-acetylneuraminate 9-phosphate; which is catalyzed by the enzyme sialic acid synthase. In humans, N-acetyl-D-mannosamine 6-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway.
Structure
Data?1582752178
Synonyms
ValueSource
2-(Acetylamino)-2-deoxy-6-O-phosphono-alpha-D-mannopyranoseChEBI
2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannopyranoseChEBI
2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannoseChEBI
2-(Acetylamino)-2-deoxy-6-O-phosphono-a-D-mannopyranoseGenerator
2-(Acetylamino)-2-deoxy-6-O-phosphono-α-D-mannopyranoseGenerator
2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannopyranoseGenerator
2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannopyranoseGenerator
2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannoseGenerator
2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannoseGenerator
N-Acetyl-D-mannosamine 6-phosphoric acidGenerator
ManNAc-6-pHMDB
N-Acetyl-D-mannosamine-6-pHMDB
N-Acetyl-D-mannosamine-6-phosphateHMDB
N-Acetylmannosamine-6-pHMDB
2-Acetamido-2-deoxy-mannose-6-phosphateHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
IUPAC Name{[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number873185-52-5
SMILES
CC(=O)N[C@@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5+,6-,7-,8+/m1/s1
InChI KeyBRGMHAYQAZFZDJ-UOLFYFMNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Acetamide
  • 1,2-diol
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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 Solubility17.6 g/LALOGPS
logP-2ALOGPS
logP-3.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m³·mol⁻¹ChemAxon
Polarizability25.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-000t-9740000000-cab3a2db3c6cb3b55bdaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-5932260000-cf5a295bb3aa57a99de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v00-5931000000-4a813f2d6d4480fc5e41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8cdef6bcf81376fb24e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a998778a46bb52c7223aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2196000000-8aa0b82454ed7fe1de1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2a-4591000000-dca968a4092f312565acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900000000-933daf9b2c351b0a86b6Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB022435
KNApSAcK IDNot Available
Chemspider ID389249
KEGG Compound IDC04257
BioCyc IDNot Available
BiGG ID43459
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440273
PDB IDBMX
ChEBI ID62165
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 ATP binding
Specific function:
Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:
GNE
Uniprot ID:
Q9Y223
Molecular weight:
83065.25
Reactions
Adenosine triphosphate + N-Acetylmannosamine → ADP + N-Acetyl-D-mannosamine 6-phosphatedetails
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 phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Lipid phosphatase that acts on phosphatidylinositol 3-phosphate and phosphatidylinositol (3,5)-bisphosphate.
Gene Name:
MTMR1
Uniprot ID:
Q13613
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup. Has phosphatase activity towards phosphatidylinositol 3-phosphate and phosphatidylinositol 3,5-bisphosphate.
Gene Name:
MTMR2
Uniprot ID:
Q13614
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup. Acts as a negative regulator of KCNN4/KCa3.1 channel activity in CD4+ T-cells possibly by decreasing intracellular levels of phosphatidylinositol 3 phosphatase. Negatively regulates proliferation of reactivated CD4+ T-cells.
Gene Name:
MTMR6
Uniprot ID:
Q9Y217
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup (Probable).
Gene Name:
MTMR7
Uniprot ID:
Q9Y216
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails