NP-MRD: Showing NP-Card for (2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid (NP0261429)

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Record Information

Version

2.0

Created at

2022-09-08 03:52:19 UTC

Updated at

2022-09-08 03:52:20 UTC

NP-MRD ID

NP0261429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Description

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006041518552D          
 
 43 45  0  0  1  0            999 V2000
    9.6130   -9.0693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9014   -8.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6130   -9.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9189  -10.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3164   -8.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908   -9.0693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9014  -10.3109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7422  -10.0507    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.3127   -7.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0200   -9.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908   -9.8882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9050  -11.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5540  -10.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7422  -10.8669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7422   -9.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3738  -10.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1496  -10.2930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8103   -9.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4097  -11.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4815  -10.3037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2401  -11.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9404  -11.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0017   -8.9352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7201  -11.6828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2866   -8.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7161   -8.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2472   -7.7008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5831   -8.9244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7161   -7.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0053   -7.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0053   -6.4734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4440   -8.6253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4471   -7.7676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7058   -7.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6657   -6.4786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4422  -10.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420   -9.4855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853   -7.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6952   -9.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420  -11.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853  -11.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993  -11.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387  -11.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  6  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  2  0  0  0  0
 13 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
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 30 31  1  0  0  0  0
  7 11  1  0  0  0  0
 20 21  1  0  0  0  0
 29 30  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 11 36  1  1  0  0  0
  6 37  1  1  0  0  0
 33 38  1  1  0  0  0
 32 39  1  6  0  0  0
 36 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
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    4.8676    1.4951   -3.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1959   -1.3898    3.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0234    1.2047   -1.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
M  END

 
  Mrv1533006041518552D          
 
 43 45  0  0  1  0            999 V2000
    9.6130   -9.0693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9014   -8.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9189  -10.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4471   -7.7676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7058   -7.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6657   -6.4786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4422  -10.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420   -9.4855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853   -7.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6952   -9.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420  -11.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853  -11.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993  -11.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387  -11.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  6  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  2  0  0  0  0
 13 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  6  0  0  0
 20 23  1  1  0  0  0
 21 24  1  6  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 29  2  0  0  0  0
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
  7 11  1  0  0  0  0
 20 21  1  0  0  0  0
 29 30  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 36  1  1  0  0  0
  6 37  1  1  0  0  0
 33 38  1  1  0  0  0
 32 39  1  6  0  0  0
 36 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(=O)CO)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H31N4O17P/c21-10-1-2-24(19(35)22-10)17-15(32)14(31)9(39-17)6-38-42(36,37)41-20(18(33)34)3-7(27)12(23-11(29)5-26)16(40-20)13(30)8(28)4-25/h1-2,7-9,12-17,25-28,30-32H,3-6H2,(H,23,29)(H,33,34)(H,36,37)(H2,21,22,35)/t7-,8+,9+,12+,13+,14+,15+,16+,17+,20+/m0/s1

> <INCHI_KEY>
HOEWKBQADMRCLO-UIUGZIMDSA-N

> <FORMULA>
C20H31N4O17P

> <MOLECULAR_WEIGHT>
630.453

> <EXACT_MASS>
630.142182552

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.671539488118896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-4-hydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.87

> <JCHEM_LOGP>
-6.5584117814695295

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.9142485151850774

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.21965169522835382

> <JCHEM_PKA_STRONGEST_BASIC>
1.4827323968684658

> <JCHEM_POLAR_SURFACE_AREA>
340.92

> <JCHEM_REFRACTIVITY>
127.12229999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cmp-N-glycoloylneuraminate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      17.944 -16.929   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.616 -16.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      17.944 -18.458   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.382 -18.761   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.257 -16.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.290 -16.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.616 -19.247   0.000  0.00  0.00           C+0
HETATM    8  P   UNK     0      21.919 -18.761   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      19.250 -14.638   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      20.571 -16.929   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.290 -18.458   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.623 -20.762   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.434 -18.761   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      21.919 -20.285   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      21.919 -17.232   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      24.964 -18.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.413 -19.214   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      27.646 -18.316   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      26.898 -20.662   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.899 -19.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.448 -20.662   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      26.022 -21.821   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      29.870 -16.679   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      29.344 -21.808   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      28.535 -15.905   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.203 -15.932   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      28.461 -14.375   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      27.222 -16.659   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      31.203 -14.382   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.877 -13.607   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      29.877 -12.084   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      13.896 -16.100   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.901 -14.499   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.518 -13.694   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.443 -12.093   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0      13.892 -19.253   0.000  0.00  0.00           N+0
HETATM   37  H   UNK     0      13.892 -17.706   0.000  0.00  0.00           H+0
HETATM   38  O   UNK     0      15.279 -13.704   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.498 -16.892   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      13.892 -20.855   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.279 -21.655   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.505 -21.655   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.085 -20.836   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    1    9   10                                                  
CONECT    6    2   11   32   37                                             
CONECT    7    3   12   11                                                  
CONECT    8    4   13   14   15                                             
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    6    7   36                                                  
CONECT   12    7                                                            
CONECT   13    8   16                                                       
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17   21   22                                                  
CONECT   20   18   23   21                                                  
CONECT   21   19   24   20                                                  
CONECT   22   19                                                            
CONECT   23   20   25   26                                                  
CONECT   24   21                                                            
CONECT   25   23   27   28                                                  
CONECT   26   23   29                                                       
CONECT   27   25   30                                                       
CONECT   28   25                                                            
CONECT   29   26   30                                                       
CONECT   30   27   31   29                                                  
CONECT   31   30                                                            
CONECT   32    6   33   39                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   11   40                                                       
CONECT   37    6                                                            
CONECT   38   33                                                            
CONECT   39   32                                                            
CONECT   40   36   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
CMP-beta-Neu5GC	ChEBI
CMP-N-Glycoloylneuraminate	ChEBI
CMP-N-Glycolylneuraminate	ChEBI
CMP-Neu5GC	ChEBI
CMP-NeuNGc	ChEBI
Cytidine-5'-monophosphono-N-glycoloyllneuraminic acid	ChEBI
CMP-b-Neu5GC	Generator
CMP-Β-neu5GC	Generator
CMP-N-Glycoloylneuraminic acid	Generator
CMP-N-Glycolylneuraminic acid	Generator
Cytidine-5'-monophosphono-N-glycoloyllneuraminate	Generator
CMP-N-Glycoloyl-b-neuraminate	Generator
CMP-N-Glycoloyl-b-neuraminic acid	Generator
CMP-N-Glycoloyl-beta-neuraminate	Generator
CMP-N-Glycoloyl-β-neuraminate	Generator
CMP-N-Glycoloyl-β-neuraminic acid	Generator
Cytidine monophosphate-N-glycoloylneuraminic acid	MeSH

Chemical Formula

C₂₀H₃₁N₄O₁₇P

Average Mass

630.4530 Da

Monoisotopic Mass

630.14218 Da

IUPAC Name

(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-4-hydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

cmp-N-glycoloylneuraminate

CAS Registry Number

Not Available

SMILES

[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(=O)CO)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C20H31N4O17P/c21-10-1-2-24(19(35)22-10)17-15(32)14(31)9(39-17)6-38-42(36,37)41-20(18(33)34)3-7(27)12(23-11(29)5-26)16(40-20)13(30)8(28)4-25/h1-2,7-9,12-17,25-28,30-32H,3-6H2,(H,23,29)(H,33,34)(H,36,37)(H2,21,22,35)/t7-,8+,9+,12+,13+,14+,15+,16+,17+,20+/m0/s1

InChI Key

HOEWKBQADMRCLO-UIUGZIMDSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside monophosphate
N-acylneuraminic acid
N-acylneuraminic acid or derivatives
Neuraminic acid
Pentose phosphate
Pentose-5-phosphate
C-glucuronide
C-glycosyl compound
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Dialkyl phosphate
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Alkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Imidolactam
Pyran
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Carboxamide group
Amino acid
Amino acid or derivatives
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organic oxide
Primary alcohol
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

CMP-N-acyl-beta-neuraminic acid (CHEBI:18098 )

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	-2.9	ALOGPS
logP	-6.6	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-0.22	ChemAxon
pKa (Strongest Basic)	1.48	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	340.92 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	127.12 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

C03691

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

656501

PDB ID

Not Available

ChEBI ID

18098

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid (NP0261429)

MOL for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

3D MOL for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

3D SDF for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

3D-SDF for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

PDB for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

3D PDB for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

SMILES for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

INCHI for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

Structure for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)

3D Structure for NP0261429 ((2r,4s,5r,6r)-2-({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid)