N-acetyl-D-glucosamine-6-phosphate

Identification

Name
N-acetyl-D-glucosamine-6-phosphate
Accession Number
DB03951  (EXPT00050)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2-acetamido-2-deoxy-6-O-phosphono-D-glucopyranose
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 301.1877
Monoisotopic: 301.056267627
Chemical Formula
C8H16NO9P
InChI Key
BRGMHAYQAZFZDJ-RTRLPJTCSA-N
InChI
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
IUPAC Name
{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlucosamine-6-phosphate isomerase 1Not AvailableHuman
UGlucosamine-6-phosphate deaminaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01062
KEGG Compound
C00357
PubChem Compound
440996
PubChem Substance
46506695
ChemSpider
389821
ChEBI
15784
HET
16G

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9954
Blood Brain Barrier-0.7722
Caco-2 permeable-0.7047
P-glycoprotein substrateNon-substrate0.733
P-glycoprotein inhibitor INon-inhibitor0.7786
P-glycoprotein inhibitor IINon-inhibitor0.9789
Renal organic cation transporterNon-inhibitor0.9623
CYP450 2C9 substrateNon-substrate0.6614
CYP450 2D6 substrateNon-substrate0.8311
CYP450 3A4 substrateNon-substrate0.5241
CYP450 1A2 substrateNon-inhibitor0.8826
CYP450 2C9 inhibitorNon-inhibitor0.905
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8757
CYP450 3A4 inhibitorNon-inhibitor0.9675
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9654
Ames testNon AMES toxic0.6072
CarcinogenicityNon-carcinogens0.9498
BiodegradationReady biodegradable0.6633
Rat acute toxicity2.3156 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9739
hERG inhibition (predictor II)Non-inhibitor0.9238
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000j-2943000000-e2bb568a8e9b660ec0be
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000j-2934000000-4140d40b85c7474418f6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-2196000000-8aa0b82454ed7fe1de1b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w2a-4591000000-dca968a4092f312565ac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dm-6900000000-933daf9b2c351b0a86b6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0v00-5931000000-4a813f2d6d4480fc5e41
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-8cdef6bcf81376fb24e2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-a998778a46bb52c7223a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0009000000-50926fdd7300073d5059
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9412000000-a1461b202e6744bf4f35
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9000000000-e7ac8ef113fa566a7265
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9000000000-364ae19f8cdb4e2d51ca
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004j-9000000000-ecee6a11feb4582407b4

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Acylaminosugars
Alternative Parents
Hexose phosphates / N-acyl-alpha-hexosamines / Monosaccharide phosphates / Monoalkyl phosphates / Oxanes / Acetamides / 1,2-diols / Secondary carboxylic acid amides / Hemiacetals / Secondary alcohols
show 6 more
Substituents
Acylaminosugar / Hexose phosphate / N-acyl-alpha-hexosamine / Monosaccharide phosphate / Monoalkyl phosphate / Monosaccharide / Organic phosphoric acid derivative / Alkyl phosphate / Oxane / Phosphoric acid ester
show 18 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acyl-D-glucosamine 6-phosphate (CHEBI:15784)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Hydrolase activity
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
Uniprot Name
Glucosamine-6-phosphate isomerase 1
Molecular Weight
32668.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Catalyzes the reversible isomerization-deamination of glucosamine 6-phosphate (GlcN6P) to form fructose 6-phosphate (Fru6P) and ammonium ion.
Gene Name
nagB
Uniprot ID
P0A759
Uniprot Name
Glucosamine-6-phosphate deaminase
Molecular Weight
29774.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:35