NP-MRD: Showing NP-Card for α-d-glucosamine 1-phosphate (NP0150299)

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Record Information

Version

1.0

Created at

2022-09-02 06:20:57 UTC

Updated at

2022-09-02 06:20:57 UTC

NP-MRD ID

NP0150299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-d-glucosamine 1-phosphate

Description

Glucosamine 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. Glucosamine 1-Phosphate is a very strong basic compound (based on its pKa). Glucosamine 1-Phosphate exists in both E. α-d-glucosamine 1-phosphate is found in Daphnia pulex and Trypanosoma brucei. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    0.6591    2.4029   -0.3747 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127    1.1431   -0.8954 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8697   -0.0284   -0.3617 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3625    0.1949    0.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291    0.1429    1.0116 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5816    1.5311    0.9088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865   -0.5944    2.4253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736   -0.8271   -0.2866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -1.2037   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305   -1.0791    0.3713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6264   -2.4382    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8082   -2.2931    1.3043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.2124   -0.4623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1622   -0.1381    0.2127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443    1.1361   -0.6035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0116    1.7883   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966    2.6066   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    3.1558   -0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561    1.2004   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7589   -0.1847   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -0.5854    2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843   -0.2074   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -0.5585    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9309   -3.0928    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266   -2.8701   -0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831   -2.0579    2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.6967   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7939    0.4846   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668    1.7721    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    1.5094   -2.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 10  1  0
 10 11  1  0
 11 12  1  0
 10  9  1  0
  9  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  5  8  1  0
  5  6  2  0
  3  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
 15 29  1  1
 16 30  1  0
 13 27  1  6
 14 28  1  0
 10 23  1  1
 11 24  1  0
 11 25  1  0
 12 26  1  0
  3 20  1  6
  7 21  1  0
  8 22  1  0
M  END


  Mrv0541 02241222352D          

 16 16  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  6  0  0  0
  2  1  1  0  0  0  0
  2 12  1  6  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  8  1  1  0  0  0
  3  5  1  0  0  0  0
  5 10  1  1  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  6  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>
NP0150299

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6-/m1/s1

> <INCHI_KEY>
YMJBYRVFGYXULK-QZABAPFNSA-N

> <FORMULA>
C6H14NO8P

> <MOLECULAR_WEIGHT>
259.151

> <EXACT_MASS>
259.045702941

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
21.237894289193314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.59

> <JCHEM_LOGP>
-4.175617677240273

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.242011904159365

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.178810463362137

> <JCHEM_PKA_STRONGEST_BASIC>
8.692592555712746

> <JCHEM_POLAR_SURFACE_AREA>
162.7

> <JCHEM_REFRACTIVITY>
48.453799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-D-glucosamine 1-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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       2.667   3.080   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    7    2    4                                                  
CONECT    2    1   12    3                                                  
CONECT    3    2    5                                                       
CONECT    4    1    8    6                                                  
CONECT    5    3   10    6                                                  
CONECT    6    4    5    9                                                  
CONECT    7    1                                                            
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    5   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

View in JSmol

Synonyms

Value	Source
2-Amino-2-deoxy-1-O-phosphono-alpha-D-glucopyranose	ChEBI
D-Glucosamine 1-phosphate	ChEBI
2-Amino-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
D-Glucosamine 1-phosphoric acid	Generator
Glucosamine 1-phosphoric acid	Generator
GLUCOSAMINE 1-phosphATE	ChEBI
a-D-Glucosamine 1-phosphate	Generator
a-D-Glucosamine 1-phosphoric acid	Generator
alpha-D-Glucosamine 1-phosphoric acid	Generator
α-D-glucosamine 1-phosphate	Generator
α-D-glucosamine 1-phosphoric acid	Generator

Chemical Formula

C₆H₁₄NO₈P

Average Mass

259.1510 Da

Monoisotopic Mass

259.04570 Da

IUPAC Name

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

Traditional Name

α-D-glucosamine 1-phosphate

CAS Registry Number

Not Available

SMILES

N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O

InChI Identifier

InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6-/m1/s1

InChI Key

YMJBYRVFGYXULK-QZABAPFNSA-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
Daphnia pulex	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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
Amino saccharide
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
1,2-aminoalcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Primary alcohol
Primary amine
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine phosphate (CHEBI:27625 )

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	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	8.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	21.24 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

External Links

HMDB ID

Not Available

DrugBank ID

DB03111

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019579

Chemspider ID

Not Available

KEGG Compound ID

C06156

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188960

PDB ID

Not Available

ChEBI ID

27625

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for α-d-glucosamine 1-phosphate (NP0150299)

MOL for NP0150299 (α-d-glucosamine 1-phosphate)

3D MOL for NP0150299 (α-d-glucosamine 1-phosphate)

3D SDF for NP0150299 (α-d-glucosamine 1-phosphate)

3D-SDF for NP0150299 (α-d-glucosamine 1-phosphate)

PDB for NP0150299 (α-d-glucosamine 1-phosphate)

3D PDB for NP0150299 (α-d-glucosamine 1-phosphate)

SMILES for NP0150299 (α-d-glucosamine 1-phosphate)

INCHI for NP0150299 (α-d-glucosamine 1-phosphate)

Structure for NP0150299 (α-d-glucosamine 1-phosphate)

3D Structure for NP0150299 (α-d-glucosamine 1-phosphate)