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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:52 UTC
HMDB IDHMDB01121
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-D-mannosamine 6-phosphate
DescriptionN-Acetyl-D-mannosamine 6-phosphate is an intermediate in amino sugar metabolism and is a substrate for UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase, Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase, Alpha-N-acetylglucosaminidase and Exostosin-2. It can be generated from N-acetyl-neuraminate-9-phosphate or N-acetyl-D-mannosamine.
Structure
Thumb
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
N-Acetyl-a-D-mannosamine 6-phosphateGenerator
N-Acetyl-a-D-mannosamine 6-phosphoric acidGenerator
N-Acetyl-alpha-D-mannosamine 6-phosphoric acidGenerator
N-Acetyl-α-D-mannosamine 6-phosphateGenerator
N-Acetyl-α-D-mannosamine 6-phosphoric acidGenerator
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
ManNAc-6-PHMDB
N-Acetyl-D-mannosamine-6-PHMDB
N-Acetyl-D-mannosamine-6-phosphateHMDB
N-Acetylmannosamine-6-PHMDB
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 KeyInChIKey=BRGMHAYQAZFZDJ-UOLFYFMNSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m3·mol-1ChemAxon
Polarizability25.24 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2196000000-8aa0b82454ed7fe1de1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2a-4591000000-dca968a4092f312565acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900000000-933daf9b2c351b0a86b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v00-5931000000-4a813f2d6d4480fc5e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8cdef6bcf81376fb24e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a998778a46bb52c7223aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseSMP00534Not Available
Salla Disease/Infantile Sialic Acid Storage DiseaseSMP00240Not Available
Sialuria or French Type SialuriaSMP00216Not Available
Sialuria or French Type SialuriaSMP00217Not Available
Tay-Sachs DiseaseSMP00390Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
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 IDFDB022435
KNApSAcK IDNot Available
Chemspider ID389249
KEGG Compound IDC04257
BioCyc IDN-ACETYL-D-MANNOSAMINE-6P
BiGG ID43459
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01121
Metagene LinkHMDB01121
METLIN IDNot Available
PubChem Compound440273
PDB IDBMX
ChEBI ID62165
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 + Phosphoric acid → 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 + Phosphoric acid → 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 + Phosphoric acid → 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 + Phosphoric acid → 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 + Phosphoric acid → 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 + Phosphoric acid → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails