NP-MRD: Showing NP-Card for 4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid (NP0269949)

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Record Information

Version

2.0

Created at

2022-09-08 15:35:10 UTC

Updated at

2022-09-08 15:35:10 UTC

NP-MRD ID

NP0269949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid

Description

4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5,6,7,12-tetrahydro-6-azatetraphen-6-yl]methyl}benzoic acid belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. 4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid is found in Streptomyces venezuelae. Based on a literature review very few articles have been published on 4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5,6,7,12-tetrahydro-6-azatetraphen-6-yl]methyl}benzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217352D          

 48 53  0  0  1  0            999 V2000
    6.1154    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4951    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753    3.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1449    4.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8453    5.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    6.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    3.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 31 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082217352D          

 48 53  0  0  1  0            999 V2000
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    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3052    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753    3.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    3.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    4.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    4.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    5.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453    5.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    6.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    3.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    2.1275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1758    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860    1.6598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5261    1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2560    2.4393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0662    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7159    3.0630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9860    3.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 37 45  1  0  0  0  0
 35 46  2  0  0  0  0
 31 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H](C[C@@H](O)[C@H]1O)OC1=C2C(=O)C3=C(C(=O)C2=CC=C1)C1=C(O)C=C(C)C=C1[C@H](CC(=O)C(O)=O)N3CC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H31NO12/c1-15-10-20-21(12-24(39)35(45)46)36(14-17-6-8-18(9-7-17)34(43)44)30-29(27(20)22(37)11-15)32(41)19-4-3-5-25(28(19)33(30)42)48-26-13-23(38)31(40)16(2)47-26/h3-11,16,21,23,26,31,37-38,40H,12-14H2,1-2H3,(H,43,44)(H,45,46)/t16-,21-,23+,26-,31-/m0/s1

> <INCHI_KEY>
OURXYGSYQVWUFL-ILDYLSGOSA-N

> <FORMULA>
C35H31NO12

> <MOLECULAR_WEIGHT>
657.628

> <EXACT_MASS>
657.184625442

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
65.21503595119687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5,6,7,12-tetrahydro-6-azatetraphen-6-yl]methyl}benzoic acid

> <JCHEM_LOGP>
3.6052322759999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.076877659305744

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.489798904040434

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2528866875223716

> <JCHEM_POLAR_SURFACE_AREA>
208.19999999999996

> <JCHEM_REFRACTIVITY>
168.64610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5H-6-azatetraphen-6-yl]methyl}benzoic acid

> <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      11.415   0.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.375  -1.558   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.391   4.844   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.903   4.553   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.407   3.098   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.911   5.718   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.407   7.173   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.424   5.427   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       5.870   3.971   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.366   5.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.375   6.591   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.870   8.046   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.879   9.210   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.391   8.919   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.399  10.083   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.911   9.792   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.895  11.538   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.895   7.464   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.887   6.300   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.187   3.971   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.195   2.807   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.707   3.098   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.715   1.934   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.211   4.553   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.723   4.844   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.203   5.718   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.707   7.173   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.691   5.427   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   18                                                       
CONECT   27   16   28   47                                                  
CONECT   28   27    6   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   46                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   46                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   45                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   37                                                       
CONECT   46   35   31   47                                                  
CONECT   47   46   27   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5,6,7,12-tetrahydro-6-azatetraphen-6-yl]methyl}benzoate	Generator

Chemical Formula

C₃₅H₃₁NO₁₂

Average Mass

657.6280 Da

Monoisotopic Mass

657.18463 Da

IUPAC Name

4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5,6,7,12-tetrahydro-6-azatetraphen-6-yl]methyl}benzoic acid

Traditional Name

4-{[(5S)-5-(2-carboxy-2-oxoethyl)-8-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5H-6-azatetraphen-6-yl]methyl}benzoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](C[C@@H](O)[C@H]1O)OC1=C2C(=O)C3=C(C(=O)C2=CC=C1)C1=C(O)C=C(C)C=C1[C@H](CC(=O)C(O)=O)N3CC1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C35H31NO12/c1-15-10-20-21(12-24(39)35(45)46)36(14-17-6-8-18(9-7-17)34(43)44)30-29(27(20)22(37)11-15)32(41)19-4-3-5-25(28(19)33(30)42)48-26-13-23(38)31(40)16(2)47-26/h3-11,16,21,23,26,31,37-38,40H,12-14H2,1-2H3,(H,43,44)(H,45,46)/t16-,21-,23+,26-,31-/m0/s1

InChI Key

OURXYGSYQVWUFL-ILDYLSGOSA-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
Streptomyces venezuelae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protopine alkaloids

Sub Class

Not Available

Direct Parent

Protopine alkaloids

Alternative Parents

Substituents

Protopine skeleton
Benzylisoquinoline
Phenanthridine
Benzoquinoline
Quinoline quinone
Naphthoquinone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Quinoline
Naphthalene
Benzoic acid
Benzoic acid or derivatives
Aryl ketone
Quinone
Phenylmethylamine
Benzylamine
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Oxane
Monosaccharide
Keto acid
Dicarboxylic acid or derivatives
Beta-aminoketone
Monocyclic benzene moiety
Alpha-keto acid
Vinylogous amide
Alpha-hydroxy ketone
Amino acid
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Amino acid or derivatives
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Enamine
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	3.61	ChemAxon
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	208.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	168.65 m³·mol⁻¹	ChemAxon
Polarizability	65.22 Å³	ChemAxon
Number of Rings	6	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163112047

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid (NP0269949)

MOL for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

3D MOL for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

3D SDF for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

3D-SDF for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

PDB for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

3D PDB for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

SMILES for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

INCHI for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

Structure for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)

3D Structure for NP0269949 (4-{[(5s)-5-(2-carboxy-2-oxoethyl)-8-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-3-methyl-7,12-dioxo-5h-6-azatetraphen-6-yl]methyl}benzoic acid)