NP-MRD: Showing NP-Card for (2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid (NP0298272)

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Record Information

Version

2.0

Created at

2022-09-10 09:23:37 UTC

Updated at

2022-09-10 09:23:38 UTC

NP-MRD ID

NP0298272

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid

Description

Bengamide A 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. (2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid is found in Rhabdastrella globostellata. (2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid was first documented in 2007 (PMID: 17656313). Based on a literature review a small amount of articles have been published on Bengamide A (PMID: 22705020) (PMID: 29476895) (PMID: 30736491) (PMID: 28185457).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211232D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102211232D          

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    2.2741   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5609   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9899   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7043   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4188   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1333   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477  -10.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5622   -9.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2767   -9.9239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9583   -9.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7467   -9.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0481  -10.4703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8708  -10.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2287  -11.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7640  -11.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0514  -11.3370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5162  -10.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3389  -10.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4094  -12.0803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9446  -12.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2321  -12.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6968  -11.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5900  -12.8852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4127  -12.9469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1253  -13.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3026  -13.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8379  -14.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1958  -14.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0152  -14.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6356  -11.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1003  -11.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8198  -11.3078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2150  -10.7466    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 22 23  1  4  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 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
 35 37  1  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 40 41  1  0  0  0  0
 17 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298272

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H](N=C(O)[C@H](OC)[C@H](O)[C@@H](O)[C@H](O)\C=C\C(C)C)C(O)=NC1

> <INCHI_IDENTIFIER>
InChI=1S/C31H56N2O8/c1-5-6-7-8-9-10-11-12-13-14-15-16-26(35)41-23-18-19-24(30(38)32-21-23)33-31(39)29(40-4)28(37)27(36)25(34)20-17-22(2)3/h17,20,22-25,27-29,34,36-37H,5-16,18-19,21H2,1-4H3,(H,32,38)(H,33,39)/b20-17+/t23-,24-,25+,27-,28+,29+/m0/s1

> <INCHI_KEY>
NKASPYGDXVCCTA-HADZOMMTSA-N

> <FORMULA>
C31H56N2O8

> <MOLECULAR_WEIGHT>
584.795

> <EXACT_MASS>
584.403666771

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
66.79395503372379

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-N-[(3S,6S)-7-hydroxy-3-(tetradecanoyloxy)-3,4,5,6-tetrahydro-2H-azepin-6-yl]-2-methoxy-8-methylnon-6-enimidic acid

> <JCHEM_LOGP>
4.718363902416141

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.5561115584331437

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.227482650131205

> <JCHEM_PKA_STRONGEST_BASIC>
4.66549981585138

> <JCHEM_POLAR_SURFACE_AREA>
161.39999999999998

> <JCHEM_REFRACTIVITY>
158.91970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-N-[(3S,6S)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3H-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.911 -17.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.245 -18.525   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.579 -17.755   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.912 -18.525   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.246 -17.755   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.580 -18.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.913 -17.755   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.247 -18.525   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.581 -17.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.914 -18.525   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.248 -17.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.582 -18.525   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.915 -17.755   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.249 -18.525   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      20.249 -20.065   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      21.583 -17.755   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.916 -18.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.189 -17.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.660 -18.111   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.223 -19.545   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      27.759 -19.660   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      28.427 -21.047   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      27.559 -22.320   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      29.963 -21.162   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.830 -19.890   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      32.366 -20.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.631 -22.550   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      29.763 -23.822   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      32.167 -22.665   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      33.034 -21.392   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      32.835 -24.052   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      34.370 -24.167   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      31.967 -25.325   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.432 -25.210   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      29.564 -26.482   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      30.232 -27.870   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      28.028 -26.367   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.453 -20.878   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      26.321 -22.151   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      23.930 -21.108   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      22.801 -20.060   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   41                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   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   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   20   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   17                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   82    0
END

View in JSmol

Synonyms

Value	Source
(3S,6S)-7-oxo-6-(((2R,3R,4S,5R,6E)-3,4,5-Trihydroxy-2-methoxy-8-methyl-6-nonenoyl)amino)-3-azepanyl myristate	MeSH

Chemical Formula

C₃₁H₅₆N₂O₈

Average Mass

584.7950 Da

Monoisotopic Mass

584.40367 Da

IUPAC Name

(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-N-[(3S,6S)-7-hydroxy-3-(tetradecanoyloxy)-3,4,5,6-tetrahydro-2H-azepin-6-yl]-2-methoxy-8-methylnon-6-enimidic acid

Traditional Name

(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-N-[(3S,6S)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3H-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H](N=C(O)[C@H](OC)[C@H](O)[C@@H](O)[C@H](O)\C=C\C(C)C)C(O)=NC1

InChI Identifier

InChI=1S/C31H56N2O8/c1-5-6-7-8-9-10-11-12-13-14-15-16-26(35)41-23-18-19-24(30(38)32-21-23)33-31(39)29(40-4)28(37)27(36)25(34)20-17-22(2)3/h17,20,22-25,27-29,34,36-37H,5-16,18-19,21H2,1-4H3,(H,32,38)(H,33,39)/b20-17+/t23-,24-,25+,27-,28+,29+/m0/s1

InChI Key

NKASPYGDXVCCTA-HADZOMMTSA-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
Rhabdastrella globostellata	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

N-acyl-alpha amino acid or derivatives
Caprolactam
Azepane
Fatty acid ester
Fatty amide
Monosaccharide
Fatty acyl
N-acyl-amine
1,2-diol
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Azacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	4.72	ChemAxon
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	4.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.4 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	158.92 m³·mol⁻¹	ChemAxon
Polarizability	66.79 Å³	ChemAxon
Number of Rings	1	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

C00027925

Chemspider ID

8252554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10077016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Johnson TA, Sohn J, Vaske YM, White KN, Cohen TL, Vervoort HC, Tenney K, Valeriote FA, Bjeldanes LF, Crews P: Myxobacteria versus sponge-derived alkaloids: the bengamide family identified as potent immune modulating agents by scrutiny of LC-MS/ELSD libraries. Bioorg Med Chem. 2012 Jul 15;20(14):4348-55. doi: 10.1016/j.bmc.2012.05.043. Epub 2012 May 24. [PubMed:22705020 ]
Tietjen I, Williams DE, Read S, Kuang XT, Mwimanzi P, Wilhelm E, Markle T, Kinloch NN, Naphen CN, Tenney K, Mesplede T, Wainberg MA, Crews P, Bell B, Andersen RJ, Brumme ZL, Brockman MA: Inhibition of NF-kappaB-dependent HIV-1 replication by the marine natural product bengamide A. Antiviral Res. 2018 Apr;152:94-103. doi: 10.1016/j.antiviral.2018.02.017. Epub 2018 Feb 22. [PubMed:29476895 ]
Jamison MT, Wang X, Cheng T, Molinski TF: Synergistic Anti-Candida Activity of Bengazole A in the Presence of Bengamide A dagger. Mar Drugs. 2019 Feb 7;17(2):102. doi: 10.3390/md17020102. [PubMed:30736491 ]
White KN, Tenney K, Crews P: The Bengamides: A Mini-Review of Natural Sources, Analogues, Biological Properties, Biosynthetic Origins, and Future Prospects. J Nat Prod. 2017 Mar 24;80(3):740-755. doi: 10.1021/acs.jnatprod.6b00970. Epub 2017 Feb 10. [PubMed:28185457 ]
Hu X, Dang Y, Tenney K, Crews P, Tsai CW, Sixt KM, Cole PA, Liu JO: Regulation of c-Src nonreceptor tyrosine kinase activity by bengamide A through inhibition of methionine aminopeptidases. Chem Biol. 2007 Jul;14(7):764-74. doi: 10.1016/j.chembiol.2007.05.010. [PubMed:17656313 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid (NP0298272)

MOL for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

3D MOL for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

3D SDF for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

3D-SDF for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

PDB for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

3D PDB for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

SMILES for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

INCHI for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

Structure for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)

3D Structure for NP0298272 ((2r,3r,4s,5r,6e)-3,4,5-trihydroxy-n-[(3s,6s)-2-hydroxy-6-(tetradecanoyloxy)-4,5,6,7-tetrahydro-3h-azepin-3-yl]-2-methoxy-8-methylnon-6-enimidic acid)