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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 10:30:45 UTC

Update Date

2021-09-24 10:30:45 UTC

HMDB ID

HMDB0304534

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-D-glucose 6-phosphate

Description

Mannose 6-phosphate, also known as mannose 6-phosphoric acid, is a member of the class of compounds known as hexose phosphates. Hexose phosphates are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Mannose 6-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Mannose 6-phosphate can be found in a number of food items such as japanese chestnut, rubus (blackberry, raspberry), allium (onion), and nanking cherry, which makes mannose 6-phosphate a potential biomarker for the consumption of these food products. Mannose 6-phosphate may be a unique E.coli metabolite. The M6P-tagged lysosomal enzymes are shipped to the late endosomes via vesicular transport. Enzyme replacement therapy (ERT) for several lysosomal storage diseases relies on this pathway to efficiently direct synthetic enzymes to the lysosome where each can metabolize its particular substrate. The pH in the late endosome can reach 6.0, which causes dissociation of M6P from its receptor. Upon release, the enzymes are ferried to their final destination in the lysosomes. The MPRs are packed into vesicles that bud off the late endosome and return to the "trans"-Golgi network. In this way, the MPRs can be recycle.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 03261516282D          

 16 16  0  0  0  0            999 V2000
   -0.0837    0.7970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -0.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452    0.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126   -0.8530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -0.8530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271    0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416    0.7971    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972    0.7990    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.9416   -0.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    1.6002    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 16  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  6  8  1  0  0  0  0
  5 11  1  0  0  0  0
  4 10  1  0  0  0  0
  3  9  1  0  0  0  0
M  CHG  2  14  -1  16  -1
M  END
> <DATABASE_ID>
HMDB0304534

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1OC(COP([O-])([O-])=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/p-2

> <INCHI_KEY>
NBSCHQHZLSJFNQ-UHFFFAOYSA-L

> <FORMULA>
C6H11O9P

> <MOLECULAR_WEIGHT>
258.12

> <EXACT_MASS>
258.015166092

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.491973365620915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-3.056105249333333

> <ALOGPS_LOGS>
-0.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.248752256962445

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.222936327751123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64935696086094

> <JCHEM_POLAR_SURFACE_AREA>
162.57000000000002

> <JCHEM_REFRACTIVITY>
44.5529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-15         0                                  
HETATM    1  O   UNK     0      -0.156   1.488   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.490   0.718   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.490  -0.822   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.156  -1.592   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.177  -0.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.177   0.718   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.824   1.488   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.511   1.488   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.824  -1.592   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.156  -3.132   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.511  -1.592   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.157   0.718   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      -5.491   1.488   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -6.715   1.491   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      -5.491  -0.052   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.511   2.987   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    3    7    1                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1    8                                                  
CONECT    7    2   12                                                       
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    7   13                                                       
CONECT   13   12   16   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0304534
HETATM    1  O1  UNL     1      -4.167   1.251  -0.192  1.00  0.00           O  
HETATM    2  P1  UNL     1      -4.001  -0.173   0.294  1.00  0.00           P  
HETATM    3  O2  UNL     1      -4.045  -1.247  -1.025  1.00  0.00           O1-
HETATM    4  O3  UNL     1      -5.239  -0.498   1.399  1.00  0.00           O1-
HETATM    5  O4  UNL     1      -2.471  -0.380   1.009  1.00  0.00           O  
HETATM    6  C1  UNL     1      -1.576   0.561   0.539  1.00  0.00           C  
HETATM    7  C2  UNL     1      -0.597  -0.009  -0.474  1.00  0.00           C  
HETATM    8  O5  UNL     1      -0.118  -1.254  -0.108  1.00  0.00           O  
HETATM    9  C3  UNL     1       1.156  -1.521  -0.576  1.00  0.00           C  
HETATM   10  O6  UNL     1       1.427  -2.868  -0.291  1.00  0.00           O  
HETATM   11  C4  UNL     1       2.206  -0.657   0.060  1.00  0.00           C  
HETATM   12  O7  UNL     1       3.326  -0.473  -0.744  1.00  0.00           O  
HETATM   13  C5  UNL     1       1.631   0.733   0.307  1.00  0.00           C  
HETATM   14  O8  UNL     1       1.265   0.778   1.638  1.00  0.00           O  
HETATM   15  C6  UNL     1       0.502   1.005  -0.645  1.00  0.00           C  
HETATM   16  O9  UNL     1       0.016   2.288  -0.394  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.061   1.430   0.045  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.051   0.982   1.430  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.162  -0.081  -1.439  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.192  -1.402  -1.686  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.369  -3.017  -0.051  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.537  -1.125   1.015  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.785   0.340  -0.386  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.393   1.526   0.139  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.032  -0.140   1.962  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.921   1.010  -1.661  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.730   2.943  -0.235  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    5    6
CONECT    6    7   17   18
CONECT    7    8   15   19
CONECT    8    9
CONECT    9   10   11   20
CONECT   10   21
CONECT   11   12   13   22
CONECT   12   23
CONECT   13   14   15   24
CONECT   14   25
CONECT   15   16   26
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Α-D-glucose 6-phosphoric acid	Generator

Chemical Formula

C₆H₁₁O₉P

Average Molecular Weight

258.12

Monoisotopic Molecular Weight

258.015166092

IUPAC Name

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate

Traditional Name

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate

CAS Registry Number

Not Available

SMILES

OC1OC(COP([O-])([O-])=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/p-2

InChI Key

NBSCHQHZLSJFNQ-UHFFFAOYSA-L

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
Organic phosphoric acid derivative
Oxane
Alkyl phosphate
Phosphoric acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a hexose-6-phosphate (MANNOSE-6P )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	162.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.55 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	155.185	32859911
AllCCS	[M+H-H2O]+	151.448	32859911
AllCCS	[M+Na]+	159.653	32859911
AllCCS	[M+NH4]+	158.655	32859911
AllCCS	[M-H]-	140.917	32859911
AllCCS	[M+Na-2H]-	140.838	32859911
AllCCS	[M+HCOO]-	140.847	32859911
DeepCCS	[M+H]+	150.618	30932474
DeepCCS	[M-H]-	148.26	30932474
DeepCCS	[M-2H]-	181.156	30932474
DeepCCS	[M+Na]+	156.711	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 10V, Positive-QTOF	splash10-0a4i-0490000000-b3fd53bffdb24df0bbcd	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 20V, Positive-QTOF	splash10-03dj-1960000000-24e14c556590d92e8b0e	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 40V, Positive-QTOF	splash10-0f6t-4900000000-3caf4b8bee63aa687ad2	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 10V, Negative-QTOF	splash10-0a4i-0090000000-35229ddd3efd37a1990b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 20V, Negative-QTOF	splash10-0a4i-6290000000-2d01316127ba65ccdb37	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-D-glucose 6-phosphate 40V, Negative-QTOF	splash10-053v-9200000000-7296d89ab58a8e9511fd	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031265

KNApSAcK ID

Not Available

Chemspider ID

3658466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4459709

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for alpha-D-glucose 6-phosphate (HMDB0304534)

MOL for HMDB0304534 (alpha-D-glucose 6-phosphate)

3D MOL for HMDB0304534 (alpha-D-glucose 6-phosphate)

3D SDF for HMDB0304534 (alpha-D-glucose 6-phosphate)

3D-SDF for HMDB0304534 (alpha-D-glucose 6-phosphate)

PDB for HMDB0304534 (alpha-D-glucose 6-phosphate)

3D PDB for HMDB0304534 (alpha-D-glucose 6-phosphate)

SMILES for HMDB0304534 (alpha-D-glucose 6-phosphate)

INCHI for HMDB0304534 (alpha-D-glucose 6-phosphate)

Structure for HMDB0304534 (alpha-D-glucose 6-phosphate)

3D Structure for HMDB0304534 (alpha-D-glucose 6-phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

NMR Spectra