MiMeDB: Showing metabocard for Fumonisin A1 (MMDBc0014980)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:53:00 UTC

Update Date

2022-12-15 22:51:45 UTC

Metabolite ID

MMDBc0014980

Metabolite Identification

Common Name

Fumonisin A1

Description

Fumonisin A1 belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions. Based on a literature review a small amount of articles have been published on Fumonisin A1.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107532D          

 63 62  0  0  1  0            999 V2000
   13.9658   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3947   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8224   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1079   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5368   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3934   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9658   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3947   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8237   -5.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5355   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1066   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -3.8743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6789   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2500   -4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1092   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6815   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2526   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8211   -4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8249   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9658   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -5.9368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -4.6993    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
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 20  2  1  6  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  3  1  6  0  0  0
 21 10  1  0  0  0  0
 22  4  1  1  0  0  0
 23  5  1  4  0  0  0
 24 15  1  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
 26 11  1  0  0  0  0
 26 13  1  0  0  0  0
 27 12  1  0  0  0  0
 27 19  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  1  0  0  0  0
 29 14  1  0  0  0  0
 30 15  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 33 18  1  0  0  0  0
 34 21  1  0  0  0  0
 34 29  1  0  0  0  0
 35 24  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 23  2  0  0  0  0
 38 23  1  0  0  0  0
 26 39  1  6  0  0  0
 27 40  1  6  0  0  0
 28 41  1  6  0  0  0
 42 30  2  0  0  0  0
 43 30  1  0  0  0  0
 44 31  2  0  0  0  0
 45 31  1  0  0  0  0
 46 32  2  0  0  0  0
 47 33  2  0  0  0  0
 48 35  2  0  0  0  0
 49 35  1  0  0  0  0
 50 36  2  0  0  0  0
 51 36  1  0  0  0  0
 29 52  1  1  0  0  0
 52 32  1  0  0  0  0
 53 33  1  0  0  0  0
 34 53  1  6  0  0  0
 20 54  1  1  0  0  0
 21 55  1  1  0  0  0
 22 56  1  6  0  0  0
 57 24  1  0  0  0  0
 58 25  1  0  0  0  0
 26 59  1  6  0  0  0
 27 60  1  6  0  0  0
 28 61  1  1  0  0  0
 29 62  1  1  0  0  0
 34 63  1  1  0  0  0
M  END


  Mrv1652305152107532D          

 63 62  0  0  1  0            999 V2000
   13.9658   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3947   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8224   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1079   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5368   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3934   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9658   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3947   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8237   -5.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5355   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1066   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -3.8743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6789   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2500   -4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1092   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6815   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2526   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8211   -4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8249   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1105   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3960   -5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9671   -5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9658   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8237   -5.9368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2526   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6815   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2513   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381   -4.6993    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
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 20  2  1  6  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  3  1  6  0  0  0
 21 10  1  0  0  0  0
 22  4  1  1  0  0  0
 23  5  1  4  0  0  0
 24 15  1  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
 26 11  1  0  0  0  0
 26 13  1  0  0  0  0
 27 12  1  0  0  0  0
 27 19  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  1  0  0  0  0
 29 14  1  0  0  0  0
 30 15  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 33 18  1  0  0  0  0
 34 21  1  0  0  0  0
 34 29  1  0  0  0  0
 35 24  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 23  2  0  0  0  0
 38 23  1  0  0  0  0
 26 39  1  6  0  0  0
 27 40  1  6  0  0  0
 28 41  1  6  0  0  0
 42 30  2  0  0  0  0
 43 30  1  0  0  0  0
 44 31  2  0  0  0  0
 45 31  1  0  0  0  0
 46 32  2  0  0  0  0
 47 33  2  0  0  0  0
 48 35  2  0  0  0  0
 49 35  1  0  0  0  0
 50 36  2  0  0  0  0
 51 36  1  0  0  0  0
 29 52  1  1  0  0  0
 52 32  1  0  0  0  0
 53 33  1  0  0  0  0
 34 53  1  6  0  0  0
 20 54  1  1  0  0  0
 21 55  1  1  0  0  0
 22 56  1  6  0  0  0
 57 24  1  0  0  0  0
 58 25  1  0  0  0  0
 26 59  1  6  0  0  0
 27 60  1  6  0  0  0
 28 61  1  1  0  0  0
 29 62  1  1  0  0  0
 34 63  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014980

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(C[C@]([H])(O)CCCC[C@@]([H])(O)C[C@]([H])(O)[C@]([H])(C)N=C(C)O)C[C@]([H])(OC(=O)CC([H])(CC(O)=O)C(O)=O)[C@]([H])(OC(=O)CC([H])(CC(O)=O)C(O)=O)[C@]([H])(C)CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C36H61NO16/c1-6-7-10-21(3)34(53-33(47)18-25(36(50)51)16-31(44)45)29(52-32(46)17-24(35(48)49)15-30(42)43)14-20(2)13-26(39)11-8-9-12-27(40)19-28(41)22(4)37-23(5)38/h20-22,24-29,34,39-41H,6-19H2,1-5H3,(H,37,38)(H,42,43)(H,44,45)(H,48,49)(H,50,51)/t20-,21+,22-,24?,25?,26+,27+,28-,29-,34+/m0/s1

> <INCHI_KEY>
ADACAMXIRQREOB-GLLJHFILSA-N

> <FORMULA>
C36H61NO16

> <MOLECULAR_WEIGHT>
763.875

> <EXACT_MASS>
763.399034888

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
80.01634102707561

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-19-[(1-hydroxyethylidene)amino]-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)butanedioic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
1.4777033261693215

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.7822388334083654

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3094292066449977

> <JCHEM_PKA_STRONGEST_BASIC>
4.231160066013111

> <JCHEM_POLAR_SURFACE_AREA>
295.08000000000004

> <JCHEM_REFRACTIVITY>
185.67120000000017

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-19-[(1-hydroxyethylidene)amino]-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      26.069  -9.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.403  -5.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.738 -10.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.066  -5.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.065  -8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.403 -10.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.737  -9.542   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.068  -7.232   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.735  -8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.070 -10.312   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.402  -8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.401  -7.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.069  -8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.737  -8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.405  -5.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.073  -7.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.738  -5.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.405  -7.232   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.734  -7.232   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.403  -7.232   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.404  -9.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.066  -7.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.399  -7.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.072  -4.922   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      36.739  -8.002   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.736  -7.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.067  -8.002   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.400  -8.002   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.070  -7.232   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.739  -4.922   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      39.406  -8.002   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.404  -4.922   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      34.072  -8.002   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      31.404  -8.002   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      34.072  -3.382   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.739  -9.542   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      12.733  -8.002   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0      11.399  -5.692   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      24.736  -5.692   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      18.067  -9.542   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      15.400  -9.542   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      36.739  -3.382   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      38.073  -5.692   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      40.740  -7.232   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      39.406  -9.542   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      31.404  -3.382   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      34.072  -9.542   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      32.738  -2.612   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      35.405  -2.612   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      38.073 -10.312   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      35.405 -10.312   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      30.070  -5.692   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      32.738  -7.232   0.000  0.00  0.00           O+0
HETATM   54  H   UNK     0      26.069  -6.462   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      31.404 -11.082   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      15.400  -6.462   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      34.072  -6.462   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      36.739  -6.462   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      24.736  -8.772   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      18.067  -6.462   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      14.066  -8.772   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      30.070  -8.772   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      32.738  -8.772   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6    1    7                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    7   21                                                       
CONECT   11    8   26                                                       
CONECT   12    9   27                                                       
CONECT   13   20   26                                                       
CONECT   14   20   29                                                       
CONECT   15   24   30                                                       
CONECT   16   25   31                                                       
CONECT   17   24   32                                                       
CONECT   18   25   33                                                       
CONECT   19   27   28                                                       
CONECT   20    2   13   14   54                                             
CONECT   21    3   10   34   55                                             
CONECT   22    4   28   37   56                                             
CONECT   23    5   37   38                                                  
CONECT   24   15   17   35   57                                             
CONECT   25   16   18   36   58                                             
CONECT   26   11   13   39   59                                             
CONECT   27   12   19   40   60                                             
CONECT   28   19   22   41   61                                             
CONECT   29   14   34   52   62                                             
CONECT   30   15   42   43                                                  
CONECT   31   16   44   45                                                  
CONECT   32   17   46   52                                                  
CONECT   33   18   47   53                                                  
CONECT   34   21   29   53   63                                             
CONECT   35   24   48   49                                                  
CONECT   36   25   50   51                                                  
CONECT   37   22   23                                                       
CONECT   38   23                                                            
CONECT   39   26                                                            
CONECT   40   27                                                            
CONECT   41   28                                                            
CONECT   42   30                                                            
CONECT   43   30                                                            
CONECT   44   31                                                            
CONECT   45   31                                                            
CONECT   46   32                                                            
CONECT   47   33                                                            
CONECT   48   35                                                            
CONECT   49   35                                                            
CONECT   50   36                                                            
CONECT   51   36                                                            
CONECT   52   29   32                                                       
CONECT   53   33   34                                                       
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   22                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   34                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  124    0
END

Synonyms

Not Available

Molecular Formula

C₃₆H₆₁NO₁₆

Average Mass

763.875

Monoisotopic Mass

763.399034888

IUPAC Name

2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-19-[(1-hydroxyethylidene)amino]-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)butanedioic acid

Traditional Name

2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-19-[(1-hydroxyethylidene)amino]-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)butanedioic acid

CAS Registry Number

Not Available

SMILES

[H][C@](C)(C[C@]([H])(O)CCCC[C@@]([H])(O)C[C@]([H])(O)[C@]([H])(C)N=C(C)O)C[C@]([H])(OC(=O)CC([H])(CC(O)=O)C(O)=O)[C@]([H])(OC(=O)CC([H])(CC(O)=O)C(O)=O)[C@]([H])(C)CCCC

InChI Identifier

InChI=1S/C36H61NO16/c1-6-7-10-21(3)34(53-33(47)18-25(36(50)51)16-31(44)45)29(52-32(46)17-24(35(48)49)15-30(42)43)14-20(2)13-26(39)11-8-9-12-27(40)19-28(41)22(4)37-23(5)38/h20-22,24-29,34,39-41H,6-19H2,1-5H3,(H,37,38)(H,42,43)(H,44,45)(H,48,49)(H,50,51)/t20-,21+,22-,24?,25?,26+,27+,28-,29-,34+/m0/s1

InChI Key

ADACAMXIRQREOB-GLLJHFILSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Fumonisins

Direct Parent

Fumonisins

Alternative Parents

Substituents

Fumonisin-skeleton
Fumonisin skeleton
Hexacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Acetamide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Polyol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	0.31	ALOGPS
logP	1.48	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	4.23	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	295.08 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	185.67 m³·mol⁻¹	ChemAxon
Polarizability	80.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00056557

Chemspider ID

78443413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587193

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Fumonisin A1 (MMDBc0014980)

MOL for #<Metabolite:0x00007f46e0822598>

3D MOL for #<Metabolite:0x00007f46e0822598>

3D SDF for #<Metabolite:0x00007f46e0822598>

3D-SDF for #<Metabolite:0x00007f46e0822598>

PDB for #<Metabolite:0x00007f46e0822598>

3D PDB for #<Metabolite:0x00007f46e0822598>

SMILES for #<Metabolite:0x00007f46e0822598>

INCHI for #<Metabolite:0x00007f46e0822598>

Structure for #<Metabolite:0x00007f46e0822598>

3D Structure for #<Metabolite:0x00007f46e0822598>