alpha-D-glucose-1-phosphate

Identification

Name
alpha-D-glucose-1-phosphate
Accession Number
DB02843  (EXPT01520)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • glucose-1-phosphate
Categories
Not Available
UNII
CIX3U01VAU
CAS number
59-56-3
Weight
Average: 260.1358
Monoisotopic: 260.029718526
Chemical Formula
C6H13O9P
InChI Key
HXXFSFRBOHSIMQ-VFUOTHLCSA-N
InChI
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1
IUPAC Name
{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
SMILES
OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhosphomannomutase/phosphoglucomutaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UGlycogen phosphorylase, muscle formNot AvailableHuman
UGlucose-1-phosphate thymidylyltransferaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UMaltodextrin phosphorylaseNot AvailableEscherichia coli (strain K12)
UGlucose-1-phosphataseNot 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
KEGG Compound
C00103
PubChem Compound
65533
PubChem Substance
46504861
ChemSpider
58977
BindingDB
23188
ChEBI
29042
HET
G1P
PDB Entries
1g0r / 1g23 / 1h5r / 1l5v / 1nt4 / 1p5d / 1uxq / 1uxt / 2b0c / 2ux8
show 10 more

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
PropertyValueSource
water solubility1E+006 mg/LMERCK INDEX (1996); extremely soluble
pKa1.11MERCK INDEX (1996); pK1
Predicted Properties
PropertyValueSource
Water Solubility32.3 mg/mLALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9872
Blood Brain Barrier+0.8276
Caco-2 permeable-0.7291
P-glycoprotein substrateNon-substrate0.6877
P-glycoprotein inhibitor INon-inhibitor0.8008
P-glycoprotein inhibitor IINon-inhibitor0.99
Renal organic cation transporterNon-inhibitor0.909
CYP450 2C9 substrateNon-substrate0.7999
CYP450 2D6 substrateNon-substrate0.8332
CYP450 3A4 substrateNon-substrate0.5878
CYP450 1A2 substrateNon-inhibitor0.917
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9692
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9751
Ames testNon AMES toxic0.7654
CarcinogenicityNon-carcinogens0.917
BiodegradationReady biodegradable0.7227
Rat acute toxicity2.0534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9038
hERG inhibition (predictor II)Non-inhibitor0.8874
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-MSsplash10-014i-0890000000-cb800147fb5e99a510e7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0090000000-2a3b56296e3be19cb31e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-5190000000-fdc51a7b0fd975e56650
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-69de35d5ce6872252869
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-9963fa05cb28ee4e9750
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-817af0fa07de830dfcf8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0090000000-2322457ec511bd92510d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-5090000000-d986f523677b1a7addcd
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-ce71459726865b116c97
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-41baf1958afa8e1bca49
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-bfea8e3efab209c2697e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-1090000000-8e32630bfab3f0ed6178
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-0c85f2f24f79558bd95e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-9030000000-cc7fbcb760461482d91a
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Monosaccharide phosphates
Alternative Parents
Hexoses / Monoalkyl phosphates / Oxanes / Secondary alcohols / Polyols / Oxacyclic compounds / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Hexose monosaccharide / Monosaccharide phosphate / Monoalkyl phosphate / Organic phosphoric acid derivative / Oxane / Alkyl phosphate / Phosphoric acid ester / Secondary alcohol / Oxacycle / Organoheterocyclic compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-glucopyranose 1-phosphate (CHEBI:29042)

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Phosphomannomutase activity
Specific Function
Highly reversible phosphoryltransferase. The phosphomannomutase activity produces a precursor for alginate polymerization, the alginate layer causes a mucoid phenotype and provides a protective bar...
Gene Name
algC
Uniprot ID
P26276
Uniprot Name
Phosphomannomutase/phosphoglucomutase
Molecular Weight
50295.09 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
Human
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis.
Gene Name
rmlA
Uniprot ID
Q9HU22
Uniprot Name
Glucose-1-phosphate thymidylyltransferase
Molecular Weight
32456.65 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
malP
Uniprot ID
P00490
Uniprot Name
Maltodextrin phosphorylase
Molecular Weight
90521.74 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
Glucose-1-phosphatase activity
Specific Function
Absolutely required for the growth of E.coli in a high-phosphate medium containing G-1-P as the sole carbon source.
Gene Name
agp
Uniprot ID
P19926
Uniprot Name
Glucose-1-phosphatase
Molecular Weight
45682.62 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 August 02, 2018 04:57