NP-MRD: Showing NP-Card for Maduramycin A (NP0333611)

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Record Information

Version

2.0

Created at

2024-07-16 06:45:13 UTC

Updated at

2026-02-04 18:10:06 UTC

NP-MRD ID

NP0333611

Natural Product DOI

https://doi.org/10.57994/3090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Maduramycin A

Description

Maduramycin A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Maduramycin A was first documented in 2024 (PMID: 39318040). Based on a literature review very few articles have been published on Maduramycin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03302309192D          

 65 69  0  0  1  0            999 V2000
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   12.8605   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1460   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.4289  -17.3250    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
  3  2  1  1  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
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  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
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 45 64  2  0  0  0  0
 43 65  1  0  0  0  0
  3 65  1  0  0  0  0
M  END


  Mrv2104 03302309192D          

 65 69  0  0  1  0            999 V2000
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C(=O)N[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O[C@H]3O[C@@H](CO[C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1O)=C/C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C43H61NO21/c1-20(10-7-13-22-11-4-3-5-12-22)8-6-9-21(2)14-15-27(48)44-40-36(57)38(30(51)24(17-46)60-40)64-43-37(58)39(31(52)25(18-47)62-43)65-42-35(56)33(54)29(50)26(63-42)19-59-41-34(55)32(53)28(49)23(16-45)61-41/h3-15,23-26,28-43,45-47,49-58H,16-19H2,1-2H3,(H,44,48)/b8-6+,13-7+,15-14+,20-10+,21-9+/t23-,24-,25-,26-,28-,29-,30-,31-,32+,33+,34-,35-,36-,37-,38+,39+,40-,41-,42+,43+/m0/s1

> <INCHI_KEY>
FPLLIJPSJZQETK-XLYSCQNDSA-N

> <FORMULA>
C43H61NO21

> <MOLECULAR_WEIGHT>
927.947

> <EXACT_MASS>
927.373607988

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
96.1395502985837

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4,8-dimethyl-11-phenylundeca-2,4,6,8,10-pentaenamide

> <JCHEM_LOGP>
-3.5780641376666678

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.919115341351572

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.464357939579292

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6552454516958686

> <JCHEM_POLAR_SURFACE_AREA>
356.7

> <JCHEM_REFRACTIVITY>
224.51920000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E,10E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4,8-dimethyl-11-phenylundeca-2,4,6,8,10-pentaenamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-23         0                                  
HETATM    1  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003 -19.250   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.338 -16.170   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      17.338 -19.250   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      21.339 -13.860   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.005 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.339  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      21.339  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      22.673 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.006  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      24.006 -12.320   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      22.673 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      22.673 -19.250   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      20.005 -20.790   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      14.670 -20.790   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       6.668 -19.250   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.667 -27.720   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334 -28.490   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.000 -27.720   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.334 -30.030   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000 -30.800   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.000 -32.340   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -1.334 -33.110   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -1.334 -34.650   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -2.667 -35.420   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -4.001 -34.650   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -4.001 -33.110   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -2.667 -32.340   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       8.002 -21.560   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   65                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   41                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   39                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   39                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   19   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   17   38                                                  
CONECT   38   37                                                            
CONECT   39   15    8   40                                                  
CONECT   40   39                                                            
CONECT   41    6   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   65                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   64                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   58                                                       
CONECT   64   45                                                            
CONECT   65   43    3                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₁NO₂₁

Average Mass

927.9470 Da

Monoisotopic Mass

927.37361 Da

IUPAC Name

(2E,4E,6E,8E,10E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4,8-dimethyl-11-phenylundeca-2,4,6,8,10-pentaenamide

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\C(=O)N[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O[C@H]3O[C@@H](CO[C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1O)=C/C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C43H61NO21/c1-20(10-7-13-22-11-4-3-5-12-22)8-6-9-21(2)14-15-27(48)44-40-36(57)38(30(51)24(17-46)60-40)64-43-37(58)39(31(52)25(18-47)62-43)65-42-35(56)33(54)29(50)26(63-42)19-59-41-34(55)32(53)28(49)23(16-45)61-41/h3-15,23-26,28-43,45-47,49-58H,16-19H2,1-2H3,(H,44,48)/b8-6+,13-7+,15-14+,20-10+,21-9+/t23-,24-,25-,26-,28-,29-,30-,31-,32+,33+,34-,35-,36-,37-,38+,39+,40-,41-,42+,43+/m0/s1

InChI Key

FPLLIJPSJZQETK-XLYSCQNDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.152470926, C2D6OS, simulated)	[email protected]	Nanjing University	Yan Zou	2024-07-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Actinomadura glauciflava		Not Available
Actinomadura glauciflava		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Fatty n-acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Amino saccharide
Fatty acyl
Benzenoid
Oxane
N-acyl-amine
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxamide group
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-3.6	ChemAxon
pKa (Strongest Acidic)	11.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	356.7 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	224.52 m³·mol⁻¹	ChemAxon
Polarizability	96.14 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Maduramycin A (NP0333611)

MOL for NP0333611 (Maduramycin A)

3D MOL for NP0333611 (Maduramycin A)

3D SDF for NP0333611 (Maduramycin A)

3D-SDF for NP0333611 (Maduramycin A)

PDB for NP0333611 (Maduramycin A)

3D PDB for NP0333611 (Maduramycin A)

SMILES for NP0333611 (Maduramycin A)

INCHI for NP0333611 (Maduramycin A)

Structure for NP0333611 (Maduramycin A)

3D Structure for NP0333611 (Maduramycin A)