MiMeDB: Showing metabocard for D-Mannose 1-phosphate (MMDBc0029651)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:09 UTC

Update Date

2022-08-31 14:16:31 UTC

Metabolite ID

MMDBc0029651

Metabolite Identification

Common Name

D-Mannose 1-phosphate

Description

D-Mannose 1-phosphate is a normal metabolite intermediate in the Fructose and mannose metabolism, and substrate of phosphomannomutase 1 (PMM, EC: 5.4.2.8), an enzyme necessary for the synthesis of GDP-mannose. PMM converts mannose 6-phosphate to mannose-1-phosphate, which is required for the synthesis of GDP-mannose, a substrate for dolichol-linked oligosaccharide synthesis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231216312D          

 16 16  0  0  0  0            999 V2000
   -0.2387    0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -0.4807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1902   -0.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387   -0.8932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2387   -1.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532   -0.4807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6677   -0.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.3443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6677    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152    1.5818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152    0.7568    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -0.0682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1  2  1  0  0  0  0
  9  7  1  0  0  0  0
  7  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  1  0  0  0
  5  6  1  1  0  0  0
  7  8  1  6  0  0  0
  9 10  1  1  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>
MMDBc0029651

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
HXXFSFRBOHSIMQ-QTVWNMPRSA-N

> <FORMULA>
C6H13O9P

> <MOLECULAR_WEIGHT>
260.1358

> <EXACT_MASS>
260.029718526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
20.682088928835967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.056105249333333

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2188934582423325

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1553718480897146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810995814615806

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
46.796299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-mannose 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.446   1.413   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.888   0.643   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.888  -0.897   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.222  -1.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.446  -1.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.446  -3.207   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.779  -0.897   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.113  -1.667   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.779   0.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.113   1.413   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.447   0.643   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.222   1.413   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.762   2.953   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.302   1.413   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       3.762   1.413   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0       3.762  -0.127   0.000  0.00  0.00           O+0
CONECT    1    9    2                                                       
CONECT    2    1    3   12                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    9    5    8                                                  
CONECT    8    7                                                            
CONECT    9    1    7   10                                                  
CONECT   10    9   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
D-Mannose 1-phosphates	ChEBI
Mannose 1-phosphate	ChEBI
Mannose 1-phosphoric acid	Generator
D-Mannose 1-phosphoric acid	Generator
1-(Dihydrogen phosphate)-D-mannopyranose	HMDB
1-(Dihydrogen phosphate)-delta-mannopyranose	HMDB
alpha-D-Mannose 1-phosphate	HMDB
alpha-delta-Mannose 1-phosphate	HMDB
D-Mannose-1-phosphate	HMDB
delta-Mannose 1-phosphates	HMDB
delta-Mannose-1-phosphate	HMDB
Mannose 1-phosphate-mannopyranose	HMDB
Mannose-1-P	HMDB

Molecular Formula

C₆H₁₃O₉P

Average Mass

260.1358

Monoisotopic Mass

260.029718526

IUPAC Name

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

Traditional Name

D-mannose 1-phosphate

CAS Registry Number

27251-84-9

SMILES

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

InChI Identifier

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

InChI Key

HXXFSFRBOHSIMQ-QTVWNMPRSA-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
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

mannose phosphate (CHEBI:35374 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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	20.68 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
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-014i-1893000000-0ec9e139257029be0d07	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1893000000-0ec9e139257029be0d07	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-ee60e23a7f8053dae6d3	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0fsi-3930250000-c69e78c38872d5ee6b95	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-9480000000-6d21f499da6e13bbe38d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-68aeffe1ebca2d4d4362	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfc211275bafe42581ae	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9240000000-4057005941a73b47e92b	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-2b520b8d7520453613e5	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9100000000-adafd3ed58bf5371e4a1	2015-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000230	ADP-Mannose	Adenosine monophosphate	Nudix (nucleoside diphosphate linked moiety x)-type motif 5	ADPmannose Diphosphatase	VMH	10567213 10722730 12717453
MMDBr0002486	Guanosine triphosphate	Guanosine diphosphate mannose	Gdp-mannose pyrophosphorylase a	GTP:Alpha-D-Mannose-1-Phosphate Guanylyltransferase	VMH	10025667 8549746 9451026
MMDBr0003985	Adenosine triphosphate	ADP	Not Available	RE1508C	VMH	10085245
MMDBr0007483	Guanosine diphosphate	Guanosine diphosphate mannose	Not Available	Mannose-1-Phosphate Guanylyltransferase (GDP)	VMH	30371894
MMDBr0007530	D-Mannose 1-phosphate	Mannose 6-phosphate	Not Available	Phosphomannomutase	VMH	30371894
MMDBr0008361	Guanosine triphosphate	Guanosine diphosphate mannose	Not Available	Mannose-1-phosphate guanylyltransferase	VMH	30371894
MMDBr0018329	alpha-D-mannose 6-phosphate	D-Mannose 1-phosphate	Phosphomannomutase	Transfers of a phosphate group; Isomerization	PathBank	31602464
MMDBr0018330	Hydrogen Ion	Guanosine diphosphate mannose	Mannose-1-phosphate guanylyltransferase	Transfer of a GMP	PathBank	31602464
MMDBr0019483	Mannose 6-phosphate	D-Mannose 1-phosphate	Phosphomannomutase	Transfers of a phosphate group; Isomerization	PathBank	31602464
MMDBr0019560	Hydrogen Ion	Guanosine diphosphate mannose	Mannose-1-phosphate guanyltransferase		PathBank	31602464

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	130	Human feces; Human sputum; Human pleural fluid plaque; Human ; Human feces; pleural fluid plaque; bal; Human stool; Human unknown; Pig ; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	80	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	251	Human feces; Human ; Human stool; Pig ; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

DB02867

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023892

KNApSAcK ID

C00007389

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mannose_1-phosphate

METLIN ID

Not Available

PubChem Compound

644175

PDB ID

Not Available

ChEBI ID

35374

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pirard M, Achouri Y, Collet JF, Schollen E, Matthijs G, Van Schaftingen E: Kinetic properties and tissular distribution of mammalian phosphomannomutase isozymes. Biochem J. 1999 Apr 1;339 ( Pt 1):201-7. [PubMed:10085245 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 ]

Showing metabocard for D-Mannose 1-phosphate (MMDBc0029651)

MOL for #<Metabolite:0x000055d24b1b7d30>

3D MOL for #<Metabolite:0x000055d24b1b7d30>

3D SDF for #<Metabolite:0x000055d24b1b7d30>

3D-SDF for #<Metabolite:0x000055d24b1b7d30>

PDB for #<Metabolite:0x000055d24b1b7d30>

3D PDB for #<Metabolite:0x000055d24b1b7d30>

SMILES for #<Metabolite:0x000055d24b1b7d30>

INCHI for #<Metabolite:0x000055d24b1b7d30>

Structure for #<Metabolite:0x000055d24b1b7d30>

3D Structure for #<Metabolite:0x000055d24b1b7d30>