alpha-D-mannose 1-phosphate (YMDB00831)

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Identification

YMDB ID

YMDB00831

Name

alpha-D-mannose 1-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Mannose 1-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. D-Mannose 1-phosphate exists in all living species, ranging from bacteria to plants to humans. In yeast, D-mannose 1-phosphate is involved in the metabolic pathway called the mannose metabolism pathway. Based on a literature review a significant number of articles have been published on D-Mannose 1-phosphate.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

1-(dihydrogen phosphate)-D-Mannopyranose
1-(dihydrogen phosphate)-delta-Mannopyranose
1-O-phosphono-alpha-D-mannopyranose
alpha-D-mannose 1-phosphate
alpha-delta-Mannose 1-phosphate
D-Mannose 1-phosphate
D-mannose 1-phosphates
D-mannose-1-phosphate
delta-mannose 1-phosphates
delta-mannose-1-phosphate
Mannose 1-phosphate
Mannose 1-phosphate-Mannopyranose
mannose-1-P
1-O-Phosphono-a-D-mannopyranose
1-O-Phosphono-α-D-mannopyranose
a-D-Mannose 1-phosphate
a-D-Mannose 1-phosphoric acid
alpha-D-Mannose 1-phosphoric acid
Α-D-mannose 1-phosphate
Α-D-mannose 1-phosphoric acid
D-Mannose 1-phosphoric acid
Mannose phosphate
Mannosyl phosphate
alpha-D-Mannopyranosyl phosphate
Α-D-mannopyranosyl phosphate

CAS number

27251-84-9

Weight

Average: 260.1358
Monoisotopic: 260.029718526

InChI Key

HXXFSFRBOHSIMQ-RWOPYEJCSA-N

InChI

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

α-D-mannose 1-phosphate

Chemical Formula

C₆H₁₃O₉P

SMILES

OC[C@H]1O[C@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

alpha-D-hexose 1-phosphate (CHEBI:18205 )
D-mannose 1-phosphate (CHEBI:18205 )

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	32.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	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	20.79 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

Not Available

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

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-014i-1893000000-0ec9e139257029be0d07	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1893000000-0ec9e139257029be0d07	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-ee60e23a7f8053dae6d3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, negative	splash10-0a4i-0090000000-2e5875c3e22b2e3a71a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, negative	splash10-052b-9040000000-89ecbcd295c6d0384f71	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, negative	splash10-002b-9000000000-14994c7e3eb1e8740c0c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, negative	splash10-004j-9000000000-d9caf3d442b3d1049cb7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, negative	splash10-004i-9000000000-d811f3fa31d259632f06	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-002b-9010000000-8a25a18fb090da386513	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-014i-0000090000-6be9a8a818482ea3cdc0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-066r-0080090000-079a2526bc0a82c74128	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-0a4i-0090010000-67955d75fc73e364bf18	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0a4i-0090000000-95f1d24de8e759cab1f5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-0a4i-4090000000-d83cbd491021191292e0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, negative	splash10-052b-9040000000-0f0c04a19b0af9146da8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-0002-9010000000-c9bc8b9da20017c781ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-002b-9000000000-227ba0ed92621a8da230	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-004j-9000000000-e52ce7e33a84536729c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 40V, negative	splash10-004j-9000000000-90073d80126ab47a6be6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-004i-9000000000-ee9b279cec8affdff472	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, negative	splash10-0a4i-0092300000-ec5386566d535bcfb5c4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-0090000000-487f81588e1cfed3c7c3	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9240000000-0a7885872856fe43526b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-b437590c213fb263989d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0532-9100000000-97504a02d14244b901cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-9360000000-98c3aee1d36863dc12ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-92ad15ffc9eae3eed039	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfc211275bafe42581ae	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
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Hashimoto, H., Sakakibara, A., Yamasaki, M., Yoda, K. (1997). "Saccharomyces cerevisiae VIG9 encodes GDP-mannose pyrophosphorylase, which is essential for protein glycosylation." J Biol Chem 272:16308-16314.9195935

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18205
HMDB ID	HMDB06330
Pubchem Compound ID	25245607
Kegg ID	C00636
ChemSpider ID	24604707
FOODB ID	FDB031268
Wikipedia	alpha-D-mannose_1-phosphate
BioCyc ID	MANNOSE-1P

Enzymes

Protein Details

1. Mannose-1-phosphate guanyltransferase

General function:: Involved in transferase activity
Specific function:: Involved in cell wall synthesis where it is required for glycosylation. Involved in cell cycle progression through cell- size checkpoint
Gene Name:: MPG1
Uniprot ID:: P41940
Molecular weight:: 39565.60156

Reactions

GTP + alpha-D-mannose 1-phosphate → diphosphate + GDP-mannose.

Structure for #<Compound:0xafc05864>

Enzymes

Reactions