MiMeDB: Showing metabocard for D-glucosamine 6-phosphate (MMDBc0054434)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:12:05 UTC

Update Date

2022-08-12 20:09:00 UTC

Metabolite ID

MMDBc0054434

Metabolite Identification

Common Name

D-glucosamine 6-phosphate

Description

D-glucosamine 6-phosphate, also known as D-glucosamine phosphoric acid, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. The pyranose form of D-glucosamine 6-phosphate. D-glucosamine 6-phosphate is a very strong basic compound (based on its pKa). D-glucosamine 6-phosphate may be a unique E. coli metabolite. In humans, D-glucosamine 6-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07171212452D          
 
 16 16  0  0  1  0            999 V2000
   15.4158  -11.3864    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.2337  -11.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6017  -11.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4158  -10.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4158  -12.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9391  -10.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6481  -11.3864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6481  -12.2118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3535  -10.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3535  -12.6282    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9391  -12.6170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0700  -11.3864    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   19.0700  -12.2118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3535  -13.4870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7754  -10.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7754  -12.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  6  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  1  0  0  0
 12 15  1  4  0  0  0
 13 16  1  6  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054434

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6?/m1/s1

> <INCHI_KEY>
XHMJOUIAFHJHBW-IVMDWMLBSA-N

> <FORMULA>
C6H14NO8P

> <MOLECULAR_WEIGHT>
259.151

> <EXACT_MASS>
259.045702941

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
20.953527563791006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-4.175672293724102

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.244475918446593

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2231700437457214

> <JCHEM_PKA_STRONGEST_BASIC>
8.234242859039174

> <JCHEM_POLAR_SURFACE_AREA>
162.70000000000002

> <JCHEM_REFRACTIVITY>
48.453799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-glucosamine 6-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-12         0                                  
HETATM    1  P   UNK     0      28.776 -21.255   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      30.303 -21.255   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.256 -21.255   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.776 -19.651   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      28.776 -22.851   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      31.620 -20.491   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.943 -21.255   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.943 -22.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      34.260 -20.491   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      34.260 -23.573   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      31.620 -23.552   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      35.597 -21.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.597 -22.795   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      34.260 -25.176   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      36.914 -20.491   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      36.914 -23.552   0.000  0.00  0.00           N+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7   12                                                       
CONECT   10    8   13   14                                                  
CONECT   11    8                                                            
CONECT   12    9   15   13                                                  
CONECT   13   10   16   12                                                  
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
2-Amino-2-deoxy-6-O-phosphono-D-glucopyranose	ChEBI
D-Glucosamine phosphate	ChEBI
D-Glucosamine-6-phosphate	ChEBI
D-Glucosamine phosphoric acid	Generator
D-Glucosamine-6-phosphoric acid	Generator
D-Glucosamine 6-phosphoric acid	Generator
2-amino-2-Deoxy-D-glucopyranose 6-phosphoric acid	Generator
Glucosamine 6-phosphate	MeSH
GLCN-6-P	MeSH
Glucosamine 6-phosphate, disodium salt	MeSH
Glucosamine 6-phosphate, monosodium salt	MeSH

Molecular Formula

C₆H₁₄NO₈P

Average Mass

259.151

Monoisotopic Mass

259.045702941

IUPAC Name

{[(2R,3S,4R,5R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid

Traditional Name

D-glucosamine 6-phosphate

CAS Registry Number

Not Available

SMILES

N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

XHMJOUIAFHJHBW-IVMDWMLBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucosamine 6-phosphate (CHEBI:47987 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	34.8 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	8.23	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	20.95 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 (TMS_2_7) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1490000000-d62893ba556f288f33d0	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-9740000000-e26066113bf4f9024c4c	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-9500000000-23ca3a957efb876b2141	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0699-7950000000-14fb214fc6b8035c474b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-db417a25c3d1c526bec5	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a125f5e7f8b95f10b389	2019-02-23	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
Eukaryota/Fungi	Ascomycota	9	Human feces; Human saliva; Human supragingival plaque
Viruses/Bamfordvirae	Nucleocytoviricota	1
Bacteria	Actinobacteria	60	Human ; Human feces; Cattle
Bacteria	Proteobacteria	397	Human ; Human feces; Pig ; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Human mucosa; Human sputum; Human subgingival plaque; Chicken
Archaea	Crenarchaeota	1
Archaea/Archaea	Crenarchaeota	4
Bacteria	Firmicutes	156	Human feces; Human ; Cattle
Bacteria	Cyanobacteria	29	Human
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Deinococcus-thermus	5
Bacteria	Dictyoglomi	2
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Acidobacteria	2
Archaea/Archaea	Euryarchaeota	21
Archaea	Euryarchaeota	2
Bacteria	nah	2
Bacteria	Thermotogae	6
Bacteria	Nitrospirae	1
Archaea/Archaea	nah	1
Eukaryota/Fungi	Microsporidia	1
Bacteria	Aquificae	1
Bacteria	Bacteroidetes	1	Human ; Human feces
Bacteria	Chlorobi	1
Bacteria	Spirochaetes	3	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00019580

Chemspider ID

Not Available

KEGG Compound ID

C00352

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440997

PDB ID

Not Available

ChEBI ID

47987

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 D-glucosamine 6-phosphate (MMDBc0054434)

MOL for #<Metabolite:0x00007fecb0cc3dd8>

3D MOL for #<Metabolite:0x00007fecb0cc3dd8>

3D SDF for #<Metabolite:0x00007fecb0cc3dd8>

3D-SDF for #<Metabolite:0x00007fecb0cc3dd8>

PDB for #<Metabolite:0x00007fecb0cc3dd8>

3D PDB for #<Metabolite:0x00007fecb0cc3dd8>

SMILES for #<Metabolite:0x00007fecb0cc3dd8>

INCHI for #<Metabolite:0x00007fecb0cc3dd8>

Structure for #<Metabolite:0x00007fecb0cc3dd8>

3D Structure for #<Metabolite:0x00007fecb0cc3dd8>