NP-MRD: Showing NP-Card for N-Acetyl-D-mannosamine 6-phosphate (NP0062875)

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Record Information

Version

2.0

Created at

2022-04-28 07:25:03 UTC

Updated at

2022-04-28 07:25:04 UTC

NP-MRD ID

NP0062875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-D-mannosamine 6-phosphate

Description

{[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxy}phosphonic acid 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. N-Acetyl-D-mannosamine 6-phosphate is found in Escherichia coli K1. Based on a literature review very few articles have been published on {[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxy}phosphonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.3916    1.6503    1.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3536    1.2967    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162    2.2656   -0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    0.1010    0.4866 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3925   -0.0929   -0.1341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1705    0.4951    0.4462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4436    1.3197    1.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7345   -0.4471    0.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069   -1.3387   -0.0817 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6390   -1.0004   -0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.3692   -0.6509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8598    1.1615    0.1553 P   0  0  1  0  0  5  0  0  0  0  0  0
    5.2289    0.7576   -0.1127 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6310    2.8153   -0.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    0.9553    1.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488   -1.5213   -1.1588 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4446   -2.6966   -1.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -1.5614   -0.4212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0899   -2.2094   -1.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6757    0.8749    1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582    2.5818    1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559    1.9636   -1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1030   -0.7150    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179    0.3477   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677    1.1794   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    1.7564    1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -2.3111    0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7989   -1.4780   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208   -1.3961    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    3.3616    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7541    0.0268    2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.6377   -1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280   -2.7005   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9701   -2.0093    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726   -3.1638   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  1  6
 12 14  1  0
 12 15  1  0
 12 13  2  0
  9 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  5  6  1  0
  7 26  1  0
  6 25  1  6
  9 27  1  1
 10 28  1  0
 10 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  6
 17 33  1  0
 18 34  1  1
 19 35  1  0
  5 24  1  6
  4 23  1  0
  3 22  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652304282209252D          

 19 19  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  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    0.0000    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    1.2375    0.0000 C   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
   -2.1434    1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  4 13  1  1  0  0  0
  3 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  6  0  0  0
  1 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1NC(O)=C

> <INCHI_IDENTIFIER>
InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-13H,1-2H2,(H2,14,15,16)/t4-,5-,6-,7-,8+/m1/s1

> <INCHI_KEY>
JVXDUMVCBMSFKZ-PVFLNQBWSA-N

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.188

> <EXACT_MASS>
301.056268097

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.610678618762222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.02

> <JCHEM_LOGP>
-3.1751038957992983

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.288646926883

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.223125203120385

> <JCHEM_PKA_STRONGEST_BASIC>
5.191837849248617

> <JCHEM_POLAR_SURFACE_AREA>
168.94

> <JCHEM_REFRACTIVITY>
68.19909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0      -4.001   2.310   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0      -5.335   3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.771   0.976   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.231   3.644   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    4                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
{[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxy}phosphonate	Generator

Chemical Formula

C₈H₁₆NO₉P

Average Mass

301.1880 Da

Monoisotopic Mass

301.05627 Da

IUPAC Name

{[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[(1-hydroxyethenyl)amino]oxan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-13H,1-2H2,(H2,14,15,16)/t4-,5-,6-,7-,8+/m1/s1

InChI Key

JVXDUMVCBMSFKZ-PVFLNQBWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli K1	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Secondary alcohol
Ketene acetal or derivatives
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Secondary amine
Polyol
Secondary aliphatic amine
Alkanolamine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	ALOGPS
logP	-3.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	5.19	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	168.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.2 m³·mol⁻¹	ChemAxon
Polarizability	25.61 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

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163104646

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-Acetyl-D-mannosamine 6-phosphate (NP0062875)

MOL for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

3D MOL for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

3D SDF for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

3D-SDF for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

PDB for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

3D PDB for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

SMILES for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

INCHI for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

Structure for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)

3D Structure for NP0062875 (N-Acetyl-D-mannosamine 6-phosphate)