NP-MRD: Showing NP-Card for 2-deoxy-d-glucose 6-phosphate (NP0320826)

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Record Information

Version

2.0

Created at

2022-09-11 22:42:05 UTC

Updated at

2022-09-11 22:42:05 UTC

NP-MRD ID

NP0320826

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-deoxy-d-glucose 6-phosphate

Description

2-Deoxy-D-glucose 6-phosphate belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. 2-Deoxy-D-glucose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Deoxy-D-glucose 6-phosphate may be a unique S. 2-deoxy-d-glucose 6-phosphate is found in Trypanosoma brucei. 2-deoxy-d-glucose 6-phosphate was first documented in 1967 (PMID: 4292705). Cerevisiae (yeast) metabolite (PMID: 6286601).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241222382D          

 20 19  0  0  1  0            999 V2000
   11.6522   -3.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6522   -5.2289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6522   -6.0539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6522   -6.8789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6522   -7.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3666   -3.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8272   -4.4039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8272   -5.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4772   -5.2289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8272   -6.0539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4772   -6.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8272   -6.8789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4772   -6.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3666   -8.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -7.2914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0166   -8.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -8.1164    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -8.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6522   -4.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4772   -4.4039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0  0  0  0
  2 19  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
 14  5  1  0  0  0  0
  6  1  2  0  0  0  0
 19  7  1  1  0  0  0
  2  8  1  1  0  0  0
  2  9  1  1  0  0  0
  3 10  1  1  0  0  0
  3 11  1  1  0  0  0
  4 12  1  1  0  0  0
  4 13  1  1  0  0  0
 14 17  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0320826

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O8P/c7-2-1-4(8)6(10)5(9)3-14-15(11,12)13/h2,4-6,8-10H,1,3H2,(H2,11,12,13)/t4-,5-,6+/m1/s1

> <INCHI_KEY>
MBPFNOMGYSRGQZ-PBXRRBTRSA-N

> <FORMULA>
C6H13O8P

> <MOLECULAR_WEIGHT>
244.1364

> <EXACT_MASS>
244.034803904

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
20.089646593490354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-2.9767681336666665

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.517987608446735

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4921812553975111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.25709231835586

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
46.8803

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-deoxy-D-glucose 6-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.751  -6.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.751  -9.761   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.751 -11.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.751 -12.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.751 -14.381   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.084  -5.911   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      20.211  -8.221   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0      20.211  -9.761   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0      23.291  -9.761   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      20.211 -11.301   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0      23.291 -11.301   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      20.211 -12.841   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      23.291 -12.841   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      23.084 -15.151   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      24.624 -13.611   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.164 -15.151   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0      24.624 -15.151   0.000  0.00  0.00           P+0
HETATM   18  O   UNK     0      24.624 -16.691   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.751  -8.221   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      23.291  -8.221   0.000  0.00  0.00           H+0
CONECT    1   19    6                                                       
CONECT    2   19    3    8    9                                             
CONECT    3    2    4   10   11                                             
CONECT    4    3    5   12   13                                             
CONECT    5    4   14                                                       
CONECT    6    1                                                            
CONECT    7   19                                                            
CONECT    8    2                                                            
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    4                                                            
CONECT   14    5   17                                                       
CONECT   15   17                                                            
CONECT   16   17                                                            
CONECT   17   14   15   16   18                                             
CONECT   18   17                                                            
CONECT   19    1    2    7   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Deoxyglucose 6-phosphate	ChEBI
2-Deoxyglucose 6-phosphoric acid	Generator
2-Deoxy-D-glucose 6-phosphoric acid	Generator

Chemical Formula

C₆H₁₃O₈P

Average Mass

244.1364 Da

Monoisotopic Mass

244.03480 Da

IUPAC Name

{[(2R,3S,4R)-2,3,4-trihydroxy-6-oxohexyl]oxy}phosphonic acid

Traditional Name

2-deoxy-D-glucose 6-phosphate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H13O8P/c7-2-1-4(8)6(10)5(9)3-14-15(11,12)13/h2,4-6,8-10H,1,3H2,(H2,11,12,13)/t4-,5-,6+/m1/s1

InChI Key

MBPFNOMGYSRGQZ-PBXRRBTRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Beta-hydroxy aldehyde
Alpha-hydrogen aldehyde
Secondary alcohol
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

deoxyaldohexose phosphate (CHEBI:16043 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-3	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	46.88 m³·mol⁻¹	ChemAxon
Polarizability	20.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

2-DEOXY-D-GLUCOSE-6-PHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108108

PDB ID

Not Available

ChEBI ID

16043

Good Scents ID

Not Available

References

General References

Biely P, Bauer S: Determination of intracellular 2-deoxy-D-glucose 6-phosphate and uridine diphosphate-2-deoxy-D-glucose. Anal Biochem. 1967 Sep;20(3):387-93. doi: 10.1016/0003-2697(67)90283-7. [PubMed:4292705 ]
Thompson J, Chassy BM: Novel phosphoenolpyruvate-dependent futile cycle in Streptococcus lactis: 2-deoxy-D-glucose uncouples energy production from growth. J Bacteriol. 1982 Sep;151(3):1454-65. doi: 10.1128/jb.151.3.1454-1465.1982. [PubMed:6286601 ]
LOTUS database [Link]

Showing NP-Card for 2-deoxy-d-glucose 6-phosphate (NP0320826)

MOL for NP0320826 (2-deoxy-d-glucose 6-phosphate)

3D MOL for NP0320826 (2-deoxy-d-glucose 6-phosphate)

3D SDF for NP0320826 (2-deoxy-d-glucose 6-phosphate)

3D-SDF for NP0320826 (2-deoxy-d-glucose 6-phosphate)

PDB for NP0320826 (2-deoxy-d-glucose 6-phosphate)

3D PDB for NP0320826 (2-deoxy-d-glucose 6-phosphate)

SMILES for NP0320826 (2-deoxy-d-glucose 6-phosphate)

INCHI for NP0320826 (2-deoxy-d-glucose 6-phosphate)

Structure for NP0320826 (2-deoxy-d-glucose 6-phosphate)

3D Structure for NP0320826 (2-deoxy-d-glucose 6-phosphate)