NP-MRD: Showing NP-Card for n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid (NP0146947)

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Record Information

Version

2.0

Created at

2022-09-02 02:26:58 UTC

Updated at

2022-09-02 02:26:58 UTC

NP-MRD ID

NP0146947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid

Description

Antimycin A, also known as antipiricullin or fintrol, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid is found in Streptomyces fimicarius and Streptomyces wadayamensis. n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid was first documented in 2006 (PMID: 16819166). Antimycin A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004191601182D          

 44 45  0  0  1  0            999 V2000
   -2.0429    3.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3313    5.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    4.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    1.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    2.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    3.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8150    3.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -3.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6132   -3.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186   -3.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831    3.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -4.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0829   -2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 16  2  1  0  0  0  0
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 39 22  1  0  0  0  0
 25 39  1  1  0  0  0
 17 40  1  6  0  0  0
 18 41  1  1  0  0  0
 20 42  1  1  0  0  0
 23 43  1  6  0  0  0
 25 44  1  6  0  0  0
M  END

     RDKit          3D

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   -3.0627    3.0753   -1.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    1.7418   -1.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0572    0.6220   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.1505   -1.2333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6942    1.1598   -1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1717   -1.3451   -0.6283 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5150   -2.5277   -1.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2839   -1.1130   -0.4616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1198   -2.2014   -0.7433 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8417   -3.9515   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -4.4216    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344   -5.6001    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789   -4.9168    2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5322    6.9304   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
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 39 78  1  0
 39 79  1  0
M  END


  Mrv1572004191601182D          

 44 45  0  0  1  0            999 V2000
   -2.0429    3.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3313    5.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2295   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3284    2.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    3.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3310   -3.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0831    3.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5294    2.0840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0117   -3.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528    3.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -0.2554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2704   -2.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    1.8018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3651   -1.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419   -0.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242   -3.4997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348   -1.0307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188   -4.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    3.3523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599   -1.9492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775   -1.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2239    2.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2241   -1.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417    1.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739    0.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350    2.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.6874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047    0.9441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5294    1.2590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901   -0.9312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1266    1.7299    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  6  0  0  0
 18  5  1  1  0  0  0
 19 12  1  0  0  0  0
 20 11  1  1  0  0  0
 21 13  2  0  0  0  0
 22 14  1  0  0  0  0
 23 17  1  0  0  0  0
 24 19  2  0  0  0  0
 24 21  1  0  0  0  0
 25 18  1  0  0  0  0
 25 20  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 15  2  0  0  0  0
 29 21  1  0  0  0  0
 23 30  1  1  0  0  0
 30 26  2  0  0  0  0
 15 31  1  4  0  0  0
 32 22  2  0  0  0  0
 33 24  1  0  0  0  0
 26 34  1  4  0  0  0
 35 27  2  0  0  0  0
 36 28  2  0  0  0  0
 37 17  1  0  0  0  0
 37 27  1  0  0  0  0
 38 18  1  0  0  0  0
 38 28  1  0  0  0  0
 39 22  1  0  0  0  0
 25 39  1  1  0  0  0
 17 40  1  6  0  0  0
 18 41  1  1  0  0  0
 20 42  1  1  0  0  0
 23 43  1  6  0  0  0
 25 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0146947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)OC(=O)[C@@]([H])(N=C(O)C2=C(O)C(=CC=C2)N=CO)[C@@]([H])(C)OC(=O)[C@]([H])(CCCCCC)[C@@]1([H])OC(=O)CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1

> <INCHI_KEY>
UIFFUZWRFRDZJC-SBOOETFBSA-N

> <FORMULA>
C28H40N2O9

> <MOLECULAR_WEIGHT>
548.633

> <EXACT_MASS>
548.273380876

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.42711125352694

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3S,4R,7R,8R,9S)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidic acid

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
7.1471618496666665

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.351971855183726

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2877397377417656

> <JCHEM_PKA_STRONGEST_BASIC>
0.028330233565098673

> <JCHEM_POLAR_SURFACE_AREA>
164.30999999999997

> <JCHEM_REFRACTIVITY>
143.15400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
antimycin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -3.813   6.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.218   9.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.712   8.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.428  -0.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.589   2.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.480   5.430   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.146   6.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.188   5.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.521   6.200   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.485  -7.178   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.855   5.430   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.011  -5.730   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.968  -7.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.755   7.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.065  -7.980   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.228   8.617   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.905   0.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.072   2.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.021  -4.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.855   3.890   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.022  -6.265   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.765   5.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.085  -0.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.505  -4.818   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.302   3.363   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.548  -3.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.408   3.363   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.625  -0.477   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -1.538  -6.533   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       1.558  -1.924   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      -3.582  -8.247   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.249   6.258   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.485  -3.638   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.065  -2.836   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.418   4.543   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.152  -1.924   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.638   2.030   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.805   0.513   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.292   4.543   0.000  0.00  0.00           O+0
HETATM   40  H   UNK     0       2.239   1.283   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.555   1.762   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.855   2.350   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.968  -1.738   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.836   3.229   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10   12   13                                                       
CONECT   11    9   20                                                       
CONECT   12   10   19                                                       
CONECT   13   10   21                                                       
CONECT   14   16   22                                                       
CONECT   15   29   31                                                       
CONECT   16    2    3   14                                                  
CONECT   17    4   23   37   40                                             
CONECT   18    5   25   38   41                                             
CONECT   19   12   24   26                                                  
CONECT   20   11   25   27   42                                             
CONECT   21   13   24   29                                                  
CONECT   22   14   32   39                                                  
CONECT   23   17   28   30   43                                             
CONECT   24   19   21   33                                                  
CONECT   25   18   20   39   44                                             
CONECT   26   19   30   34                                                  
CONECT   27   20   35   37                                                  
CONECT   28   23   36   38                                                  
CONECT   29   15   21                                                       
CONECT   30   23   26                                                       
CONECT   31   15                                                            
CONECT   32   22                                                            
CONECT   33   24                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   17   27                                                       
CONECT   38   18   28                                                       
CONECT   39   22   25                                                       
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   20                                                            
CONECT   43   23                                                            
CONECT   44   25                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Value	Source
Antimycin a1	ChEBI
Antimycin a1b	ChEBI
Antipiricullin	ChEBI
Fintrol	ChEBI
Virosin	ChEBI
[(2R,3S,6S,7R,8R)-3-[(3-formamido-2-Hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoic acid	Generator
Antimycin a	MeSH

Chemical Formula

C₂₈H₄₀N₂O₉

Average Mass

548.6330 Da

Monoisotopic Mass

548.27338 Da

IUPAC Name

N-[(3S,4R,7R,8R,9S)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidic acid

Traditional Name

antimycin A

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)OC(=O)[C@@]([H])(N=C(O)C2=C(O)C(=CC=C2)N=CO)[C@@]([H])(C)OC(=O)[C@]([H])(CCCCCC)[C@@]1([H])OC(=O)CC(C)C

InChI Identifier

InChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1

InChI Key

UIFFUZWRFRDZJC-SBOOETFBSA-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 fimicarius	LOTUS Database	35616633
Streptomyces wadayamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Tricarboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboximidic acid derivative
Carboximidic acid
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:22584 )
formamides (CHEBI:22584 )
benzamides (CHEBI:22584 )
lactone (CHEBI:22584 )

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	4.25	ALOGPS
logP	7.15	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	0.028	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	164.31 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	143.15 m³·mol⁻¹	ChemAxon
Polarizability	58.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-5744

BiGG ID

Not Available

Wikipedia Link

Antimycin A

METLIN ID

Not Available

PubChem Compound

14957

PDB ID

Not Available

ChEBI ID

2762

Good Scents ID

Not Available

References

General References

Maeda M, Hasebe Y, Egawa K, Shibanuma M, Nose K: Inhibition of angiogenesis and HIF-1alpha activity by antimycin A1. Biol Pharm Bull. 2006 Jul;29(7):1344-8. doi: 10.1248/bpb.29.1344. [PubMed:16819166 ]
LOTUS database [Link]

Showing NP-Card for n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid (NP0146947)

MOL for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D MOL for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D SDF for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D-SDF for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

PDB for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D PDB for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

SMILES for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

INCHI for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

Structure for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D Structure for NP0146947 (n-[(3s,4r,7r,8r,9s)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)