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Showing metabocard for N-Acetyl-D-Glucosamine 6-Phosphate (HMDB0001062)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:54 UTC
HMDB IDHMDB0001062
Secondary Accession Numbers
  • HMDB01062
Metabolite Identification
Common NameN-Acetyl-D-Glucosamine 6-Phosphate
DescriptionN-Acetyl-D-Glucosamine 6-Phosphate, also known as N-acetyl-D-glucosamine-6-p or GLCNAC6P, 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-Glucosamine 6-Phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-Glucosamine 6-Phosphate exists in all living species, ranging from bacteria to humans. Within humans, N-acetyl-D-glucosamine 6-phosphate participates in a number of enzymatic reactions. In particular, N-acetyl-D-glucosamine 6-phosphate can be biosynthesized from N-acetyl-D-glucosamine; which is mediated by the enzyme N-acetyl-D-glucosamine kinase. In addition, N-acetyl-D-glucosamine 6-phosphate can be converted into glucosamine 6-phosphate and acetic acid through its interaction with the enzyme putative N-acetylglucosamine-6-phosphate deacetylase. In humans, N-acetyl-D-glucosamine 6-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway.
Structure
Data?1582752174
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Acetamido-2-deoxy-6-O-phosphono-D-glucopyranoseChEBI
N-Acetyl-D-glucosamine 6-phosphoric acidGenerator
N-Acetyl-D-glucosamine-6-pHMDB
N-Acetyl-D-glucosamine-6-phosphateHMDB
N-Acetyl-glucosamine-6-pHMDB
N-Acetyl-glucosamine-6-phosphateHMDB
N-Acetylglucosamine-6-pHMDB
N-Acetylglucosamine 6-phosphateHMDB
GlcNAc6pHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
IUPAC Name{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number18191-20-3
SMILES
CC(=O)N[C@H]1C(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-RTRLPJTCSA-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:

Role

Industrial application:

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
Polarizability25.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9730000000-66d6101e8cb0c5ca3fc1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fk9-7391350000-2eb6c4c504e0841c1908Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-50926fdd7300073d5059Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9412000000-a1461b202e6744bf4f35Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-e7ac8ef113fa566a7265Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-364ae19f8cdb4e2d51caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-ecee6a11feb4582407b4Spectrum
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.173 +/- 0.163 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.192 +/- 0.574 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03951
Phenol Explorer Compound IDNot Available
FooDB IDFDB022401
KNApSAcK IDC00019661
Chemspider ID389821
KEGG Compound IDC00357
BioCyc IDNot Available
BiGG ID34733
Wikipedia LinkNot Available
METLIN ID5975
PubChem Compound440996
PDB IDNot Available
ChEBI ID15784
Food Biomarker OntologyNot Available
VMH IDACGAM6P
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Komatsuzawa H, Fujiwara T, Nishi H, Yamada S, Ohara M, McCallum N, Berger-Bachi B, Sugai M: The gate controlling cell wall synthesis in Staphylococcus aureus. Mol Microbiol. 2004 Aug;53(4):1221-31. [PubMed:15306023 ]

Enzymes

Enzyme Details
1. Glucosamine 6-phosphate N-acetyltransferase
General function:
Involved in N-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GNPNAT1
Uniprot ID:
Q96EK6
Molecular weight:
20748.965
Reactions
Acetyl-CoA + Glucosamine 6-phosphate → Coenzyme A + N-Acetyl-D-Glucosamine 6-Phosphatedetails
Enzyme Details
2. Glucosamine-6-phosphate isomerase 1
General function:
Involved in carbohydrate metabolic process
Specific function:
Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
Gene Name:
GNPDA1
Uniprot ID:
P46926
Molecular weight:
32668.29
Enzyme Details
3. N-acetyl-D-glucosamine kinase
General function:
Carbohydrate transport and metabolism
Specific function:
Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded. Also has ManNAc kinase activity.
Gene Name:
NAGK
Uniprot ID:
Q9UJ70
Molecular weight:
42037.295
Reactions
Adenosine triphosphate + N-Acetyl-D-glucosamine → ADP + N-Acetyl-D-Glucosamine 6-Phosphatedetails
Enzyme Details
4. Phosphoacetylglucosamine mutase
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P.
Gene Name:
PGM3
Uniprot ID:
O95394
Molecular weight:
62940.905
Reactions
N-Acetyl-glucosamine 1-phosphate → N-Acetyl-D-Glucosamine 6-Phosphatedetails
N-Acetyl-D-Glucosamine 6-Phosphate → N-Acetyl-glucosamine 1-phosphatedetails
Enzyme Details
5. Putative N-acetylglucosamine-6-phosphate deacetylase
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:
AMDHD2
Uniprot ID:
Q9Y303
Molecular weight:
63594.415
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water → Glucosamine 6-phosphate + Acetic aciddetails
Enzyme Details
6. Glucosamine-6-phosphate isomerase 2
General function:
Involved in carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Molecular weight:
27090.845