MiMeDB: Showing metabocard for alpha-D-Glucosamine 1-phosphate (MMDBc0031727)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:46:02 UTC

Update Date

2024-10-13 06:52:39 UTC

Metabolite ID

MMDBc0031727

Metabolite Identification

Common Name

alpha-D-Glucosamine 1-phosphate

Description

Alpha-D-glucosamine 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is involved and amino sugar and nucleotide sugar metabolism.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222352D          

 16 16  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  6  0  0  0
  2  1  1  0  0  0  0
  2 12  1  6  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  8  1  1  0  0  0
  3  5  1  0  0  0  0
  5 10  1  1  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 15  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031727

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
YMJBYRVFGYXULK-QZABAPFNSA-N

> <FORMULA>
C6H14NO8P

> <MOLECULAR_WEIGHT>
259.151

> <EXACT_MASS>
259.045702941

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
21.237894289193314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-2.59

> <JCHEM_LOGP>
-4.175617677240273

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.242011904159365

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.178810463362137

> <JCHEM_PKA_STRONGEST_BASIC>
8.692592555712746

> <JCHEM_POLAR_SURFACE_AREA>
162.7

> <JCHEM_REFRACTIVITY>
48.453799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-D-glucosamine 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       2.667   3.080   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    7    2    4                                                  
CONECT    2    1   12    3                                                  
CONECT    3    2    5                                                       
CONECT    4    1    8    6                                                  
CONECT    5    3   10    6                                                  
CONECT    6    4    5    9                                                  
CONECT    7    1                                                            
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    5   11                                                       
CONECT   11   10                                                            
CONECT   12    2   15                                                       
CONECT   13   15                                                            
CONECT   14   15                                                            
CONECT   15   12   13   14   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
2-Amino-2-deoxy-1-O-phosphono-alpha-D-glucopyranose	ChEBI
D-Glucosamine 1-phosphate	ChEBI
2-Amino-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
D-Glucosamine 1-phosphoric acid	Generator
Glucosamine 1-phosphoric acid	Generator
GLUCOSAMINE 1-phosphATE	ChEBI
a-D-Glucosamine 1-phosphate	Generator
a-D-Glucosamine 1-phosphoric acid	Generator
alpha-D-Glucosamine 1-phosphoric acid	Generator
α-D-glucosamine 1-phosphate	Generator
α-D-glucosamine 1-phosphoric acid	Generator

Molecular Formula

C₆H₁₄NO₈P

Average Mass

259.151

Monoisotopic Mass

259.045702941

IUPAC Name

{[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

α-D-glucosamine 1-phosphate

CAS Registry Number

Not Available

SMILES

N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O

InChI Identifier

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

InChI Key

YMJBYRVFGYXULK-QZABAPFNSA-N

Chemical Taxonomy

Description

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

Substituents

Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Amino saccharide
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
1,2-aminoalcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Primary alcohol
Primary amine
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine phosphate (CHEBI:27625 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	35.1 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	8.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	21.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9010000000-4a4369962a02bbefd288	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1390000000-19b3065167a88b742feb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ow-9550000000-52be51437d4b754c9a4d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9200000000-b0eb00d809084bbdb3d3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054t-9010000000-da9819227ffe756d390b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-42c6841338922884a12a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-21af41c3ae65f0ccd866	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	406	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Cattle ; Rat ; Turkey ; Lion ; Chicken ; River trout ; Sheep ; Human mucosa; Human sputum; Human subgingival plaque	Unknown
Bacteria	Cyanobacteria	34	Human
Bacteria	Firmicutes	165	Human feces; Human ; Catfish ; Human saliva; Cattle
Bacteria	Tenericutes	1
Bacteria	Aquificae	2
Bacteria	Actinobacteria	60	Human ; Human feces; Cattle
Bacteria	Deinococcus-thermus	5
Bacteria	Thermotogae	9
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Acidobacteria	2
Archaea/Archaea	Euryarchaeota	19
Bacteria	nah	1
Bacteria	Nitrospirae	1
Archaea/Archaea	Crenarchaeota	1
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Dictyoglomi	2
Archaea	Euryarchaeota	2
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB03111

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00019579

Chemspider ID

Not Available

KEGG Compound ID

C06156

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188960

PDB ID

Not Available

ChEBI ID

27625

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for alpha-D-Glucosamine 1-phosphate (MMDBc0031727)

MOL for #<Metabolite:0x00007fdb4c6872f0>

3D MOL for #<Metabolite:0x00007fdb4c6872f0>

3D SDF for #<Metabolite:0x00007fdb4c6872f0>

3D-SDF for #<Metabolite:0x00007fdb4c6872f0>

PDB for #<Metabolite:0x00007fdb4c6872f0>

3D PDB for #<Metabolite:0x00007fdb4c6872f0>

SMILES for #<Metabolite:0x00007fdb4c6872f0>

INCHI for #<Metabolite:0x00007fdb4c6872f0>

Structure for #<Metabolite:0x00007fdb4c6872f0>

3D Structure for #<Metabolite:0x00007fdb4c6872f0>