An official website of the United States government

alpha-D-glucosamine 1-phosphate

PubChem CID
188960
Structure
alpha-D-glucosamine 1-phosphate_small.png
alpha-D-glucosamine 1-phosphate_3D_Structure.png
Molecular Formula
Synonyms
  • alpha-D-glucosamine 1-phosphate
  • 2152-75-2
  • Glucosamine 1-phosphate
  • D-glucosamine 1-phosphate
  • [(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
Molecular Weight
259.15 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
Alpha-D-glucosamine 1-phosphate is a glucosamine phosphate. It has a role as an Escherichia coli metabolite. It is functionally related to an alpha-D-glucosamine. It is a conjugate acid of an alpha-D-glucosamine 1-phosphate(1-).
alpha-D-Glucosamine 1-phosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Glucosamine 1-phosphate has been reported in Daphnia pulex and Trypanosoma brucei with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
alpha-D-glucosamine 1-phosphate.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
a-GlcN1P
IUPAC
phosphono 2-amino-2-deoxy-alpha-D-gluco-hexopyranoside

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

3.1.2 InChI

InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.3 InChIKey

YMJBYRVFGYXULK-QZABAPFNSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.4 SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)O)N)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C6H14NO8P
Computed by PubChem 2.2 (PubChem release 2024.11.20)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 UNII

3.3.3 ChEBI ID

3.3.4 DrugBank ID

3.3.5 DSSTox Substance ID

3.3.6 KEGG ID

3.3.7 Metabolomics Workbench ID

3.3.8 Nikkaji Number

3.3.9 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

glucosamine 1-phosphate

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
259.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
-6.2
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
259.04570340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
259.04570340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
163 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
282
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Collision Cross Section

153 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
158.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

4.3 Chemical Classes

4.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 MS-MS

1 of 2
NIST Number
1171710
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
260.053
Total Peaks
116
m/z Top Peak
242
m/z 2nd Highest
224
m/z 3rd Highest
126
Thumbnail
Thumbnail
2 of 2
NIST Number
1171777
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
258.0384
Total Peaks
28
m/z Top Peak
78.9
m/z 2nd Highest
240
m/z 3rd Highest
96.9
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 Biochemical Reactions

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

9.5 Chemical-Gene Co-Occurrences in Literature

9.6 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Protein Bound 3D Structures

11.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

11.2 Chemical-Target Interactions

11.3 Pathways

12 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 NORMAN Suspect List Exchange Classification

13.5 CCSBase Classification

13.6 EPA DSSTox Classification

13.7 LOTUS Tree

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  6. ChEBI
  7. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  8. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  9. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    alpha-D-glucosamine 1-phosphate
    https://www.ymdb.ca/compounds/YMDB00754
  10. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  13. Natural Product Activity and Species Source (NPASS)
  14. Metabolomics Workbench
  15. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    D-Glucosamine 1-phosphate
    http://www.nist.gov/srd/nist1a.cfm
  16. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Glucosamine 1-phosphate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. Protein Data Bank in Europe (PDBe)
  18. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  19. Springer Nature
  20. Wikidata
    alpha-D-glucosamine 1-phosphate
    https://www.wikidata.org/wiki/Q27094063
  21. PubChem
  22. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  23. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  24. PATENTSCOPE (WIPO)
  25. NCBI
CONTENTS