D-mannose 6-phosphate (YMDB00966)

Identification

YMDB ID

YMDB00966

Name

D-mannose 6-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-mannose 6-phosphate 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. Based on a literature review a significant number of articles have been published on D-mannose 6-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

6-O-phosphono-D-mannose
alpha-D-mannose-6-P
alpha-D-mannose-6-phosphate
alpha-delta-mannose-6-P
alpha-delta-mannose-6-phosphate
D-Mannose 6-phosphate
D-Mannose, 6-(dihydrogen phosphate)
delta-Mannose 6-phosphate
Man-6-p
Mannose 6-phosphate
Mannose 6-phosphic acid
Mannose-6-phosphate
D-Mannose 6-phosphoric acid
Mannose-6-phosphate dilithium salt
Mannose-6-phosphate disodium salt
Mannose-6-phosphate sodium salt, (D)-isomer

CAS number

3672-15-9

Weight

Average: 260.1358
Monoisotopic: 260.029718526

InChI Key

NBSCHQHZLSJFNQ-QTVWNMPRSA-N

InChI

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)/t2-,3-,4+,5+,6?/m1/s1

IUPAC Name

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

Traditional IUPAC Name

mannose 6-phosphate

Chemical Formula

C₆H₁₃O₉P

SMILES

OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-hexopyranose 6-phosphate (CHEBI:48066 )
D-mannose 6-phosphate (CHEBI:48066 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	31.4 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-0.92	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	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Amino sugar and nucleotide sugar metabolism	PW002413
Mannose Metabolism	PW002391

KEGG Pathways

Amino sugar and nucleotide sugar metabolism	ec00520
Fructose and mannose metabolism	ec00051

SMPDB Reactions

Not Available

KEGG Reactions

Adenosine triphosphate + D-Mannose → D-mannose 6-phosphate + hydron + ADP

D-mannose 6-phosphate ↔ Fructose 6-phosphate

D-Mannose 1-phosphate ↔ D-mannose 6-phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9740000000-a6e81224fb97751dc2e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-94ea79ec673f4688b7a0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-5940000000-c649262446626dcb8d6e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uka-9800000000-aae2cb792906d2dec6cd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-8290000000-8e20219f94b3fe964e38	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-b19b64f5cb4124047baf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ecb75a44e3d25affdf31	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-9060000000-b446300429049a22bea4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-d5aaca13a836cb9f1725	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dm-0970000000-40dbaf3d3c72cf65bf47	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-7900000000-00bc03290b6c0bfb7f84	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-7a6ff6606f1dbc2f0ae4	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Roux, C., Lee, J. H., Jeffery, C. J., Salmon, L. (2004). "Inhibition of type I and type II phosphomannose isomerases by the reaction intermediate analogue 5-phospho-D-arabinonohydroxamic acid supports a catalytic role for the metal cofactor." Biochemistry 43:2926-2934.15005628
Foret, J., de Courcy, B., Gresh, N., Piquemal, J. P., Salmon, L. (2009). "Synthesis and evaluation of non-hydrolyzable D-mannose 6-phosphate surrogates reveal 6-deoxy-6-dicarboxymethyl-D-mannose as a new strong inhibitor of phosphomannose isomerases." Bioorg Med Chem 17:7100-7107.19783448

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17369
HMDB ID	HMDB01078
Pubchem Compound ID	65127
Kegg ID	C00275
ChemSpider ID	25057696
FOODB ID	FDB030772
Wikipedia	Mannose_6-phosphate
BioCyc ID	MANNOSE-6P

Enzymes

Protein Details

1. Hexokinase-2

General function:: Involved in ATP binding
Specific function:: Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:: HXK2
Uniprot ID:: P04807
Molecular weight:: 53942.0

Reactions

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

Protein Details

2. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:: HXK1
Uniprot ID:: P04806
Molecular weight:: 53737.89844

Reactions

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

Protein Details

3. Mannose-6-phosphate isomerase

General function:: Involved in mannose-6-phosphate isomerase activity
Specific function:: Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions
Gene Name:: PMI40
Uniprot ID:: P29952
Molecular weight:: 48188.30078

Reactions

D-mannose 6-phosphate → D-fructose 6-phosphate.

Protein Details

4. Phosphomannomutase

General function:: Involved in catalytic activity
Specific function:: Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions
Gene Name:: SEC53
Uniprot ID:: P07283
Molecular weight:: 29062.69922

Reactions

Alpha-D-mannose 1-phosphate → D-mannose 6-phosphate.

Structure for #<Compound:0xb159705c>

Enzymes

Reactions

Reactions

Reactions

Reactions