NP-MRD: Showing NP-Card for methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate (NP0270754)

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Record Information

Version

2.0

Created at

2022-09-08 16:48:19 UTC

Updated at

2022-09-08 16:48:19 UTC

NP-MRD ID

NP0270754

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate

Description

SF-2140 belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond. methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate was first documented in 1984 (PMID: 6090375). Based on a literature review very few articles have been published on SF-2140 (PMID: 6548734).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218482D          

 26 28  0  0  1  0            999 V2000
    2.0300   -5.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -4.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -3.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    1.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 12 25  1  0  0  0  0
 11 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.8702    2.8857   -0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    1.7262   -0.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7928    0.5902   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0424    0.5765   -1.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0362   -0.6156   -1.3178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6353   -1.8662   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.9681    0.7260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6329   -3.0641    1.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906   -2.0721    0.5852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0150   -2.3386    1.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -0.6973    0.0584 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2667   -0.5798    0.0463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -1.5733    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378   -1.0955    0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.8432    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937   -1.5189    1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619   -1.2455    2.7280 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.2466   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521    1.2218   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753    0.8603   -0.2320 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.6861   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491    2.5170   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.8571   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    1.8573   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    0.5562   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6789   -0.5210   -1.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536    2.6779   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258    3.2015    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996    3.6755   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306   -0.7461   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383   -1.7299   -0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2954   -2.7393   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2945   -1.0065    1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5298   -2.9309    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -2.8488   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -1.9671    2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    0.0442    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156   -2.6107    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -1.5349   -0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071   -2.9344    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844    1.3314    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009    2.7510   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863    1.5260   -1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6038    3.2652   -0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    3.8821   -0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4520    2.1121   -0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 26  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 26  5  1  0
 25 12  1  0
 25 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  9 35  1  6
 10 36  1  0
 11 37  1  1
 13 38  1  0
 15 39  1  0
 15 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END


  Mrv1652309082218482D          

 26 28  0  0  1  0            999 V2000
    2.0300   -5.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -4.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -3.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    1.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 12 25  1  0  0  0  0
 11 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270754

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@@H](O)[C@H](O)[C@H](O1)N1C=C(CC#N)C2=C(OC)C=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2O6/c1-24-13-5-3-4-11-15(13)10(6-7-19)9-20(11)17-16(22)12(21)8-14(26-17)18(23)25-2/h3-5,9,12,14,16-17,21-22H,6,8H2,1-2H3/t12-,14+,16+,17+/m1/s1

> <INCHI_KEY>
HTFYSSZLIDVAIP-QCPWZWHMSA-N

> <FORMULA>
C18H20N2O6

> <MOLECULAR_WEIGHT>
360.366

> <EXACT_MASS>
360.132136372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.40985674761984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,4R,5S,6S)-6-[3-(cyanomethyl)-4-methoxy-1H-indol-1-yl]-4,5-dihydroxyoxane-2-carboxylate

> <JCHEM_LOGP>
0.5762108906666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.807645838891919

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.632349310782857

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2514034827475955

> <JCHEM_POLAR_SURFACE_AREA>
113.94

> <JCHEM_REFRACTIVITY>
89.99280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4R,5S,6S)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       3.789 -10.376   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.759  -9.231   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.235  -7.767   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.741  -7.447   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.839  -6.118   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.363   2.048   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   26                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   14   19   25                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   18   12                                                  
CONECT   26   11    5                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl-(3-cyanomethyl-4-methoxyindole-1-yl-N-(4-deoxy-alpha lyxo-hexopyranoside))uronate	MeSH

Chemical Formula

C₁₈H₂₀N₂O₆

Average Mass

360.3660 Da

Monoisotopic Mass

360.13214 Da

IUPAC Name

methyl (2S,4R,5S,6S)-6-[3-(cyanomethyl)-4-methoxy-1H-indol-1-yl]-4,5-dihydroxyoxane-2-carboxylate

Traditional Name

methyl (2S,4R,5S,6S)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@@H](O)[C@H](O)[C@H](O1)N1C=C(CC#N)C2=C(OC)C=CC=C12

InChI Identifier

InChI=1S/C18H20N2O6/c1-24-13-5-3-4-11-15(13)10(6-7-19)9-20(11)17-16(22)12(21)8-14(26-17)18(23)25-2/h3-5,9,12,14,16-17,21-22H,6,8H2,1-2H3/t12-,14+,16+,17+/m1/s1

InChI Key

HTFYSSZLIDVAIP-QCPWZWHMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-glucuronides

Alternative Parents

Substituents

N-glucuronide
Glycosyl compound
N-glycosyl compound
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Oxane
Pyran
Substituted pyrrole
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Secondary alcohol
1,2-diol
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Nitrile
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Carbonitrile
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Cyanide
Carbonyl group
Alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.58	ChemAxon
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.99 m³·mol⁻¹	ChemAxon
Polarizability	36.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00018601

Chemspider ID

5293053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6917832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ito T, Ohba K, Koyama M, Sezaki M, Tohyama H, Shomura T, Fukuyasu H, Kazuno Y, Niwa T, Kojima M, et al.: A new antiviral antibiotic SF-2140 produced by Actinomadura. J Antibiot (Tokyo). 1984 Aug;37(8):931-4. doi: 10.7164/antibiotics.37.931. [PubMed:6090375 ]
Tohyama H, Miyadoh S, Ito M, Shomura T, Ito T, Ishikawa T, Kojima M: A new indole N-glycoside antibiotic SF-2140 from an Actinomadura. I. Taxonomy and fermentation of producing microorganism. J Antibiot (Tokyo). 1984 Oct;37(10):1144-8. doi: 10.7164/antibiotics.37.1144. [PubMed:6548734 ]
LOTUS database [Link]

Showing NP-Card for methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate (NP0270754)

MOL for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

3D MOL for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

3D SDF for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

3D-SDF for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

PDB for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

3D PDB for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

SMILES for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

INCHI for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

Structure for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)

3D Structure for NP0270754 (methyl (2s,4r,5s,6s)-6-[3-(cyanomethyl)-4-methoxyindol-1-yl]-4,5-dihydroxyoxane-2-carboxylate)