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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-21 17:58:20 UTC
HMDB IDHMDB0001062
Secondary Accession Numbers
  • HMDB01062
Metabolite Identification
Common NameN-Acetyl-D-Glucosamine 6-Phosphate
DescriptionN-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase.
Structure
Thumb
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-phosphateMeSH
GlcNAc6pMeSH
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 Number102029-88-9
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
DescriptionThis compound belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Glutamate metabolism
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
Polarizability25.8 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000j-2943000000-e2bb568a8e9b660ec0beView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000j-2934000000-4140d40b85c7474418f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-50926fdd7300073d5059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9412000000-a1461b202e6744bf4f35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-e7ac8ef113fa566a7265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-364ae19f8cdb4e2d51caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-ecee6a11feb4582407b4View in MoNA
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 Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
2-Hydroxyglutric Aciduria (D And L Form)Pw000212Pw000212 greyscalePw000212 simpleNot Available
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyPw000070Pw000070 greyscalePw000070 simpleNot Available
Amino Sugar MetabolismPw000008Pw000008 greyscalePw000008 simpleMap00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseasePw000510Pw000510 greyscalePw000510 simpleNot Available
Glutamate MetabolismPw000003Pw000003 greyscalePw000003 simpleMap00250
Displaying entries 1 - 5 of 12 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022401
KNApSAcK IDNot Available
Chemspider ID389821
KEGG Compound IDC00357
BioCyc IDN-ACETYL-D-GLUCOSAMINE-6-P
BiGG ID34733
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0001062
METLIN ID5975
PubChem Compound440996
PDB ID1FRZ
ChEBI ID15784
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

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
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
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
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
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
General function:
Involved in carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Molecular weight:
27090.845