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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:08:38 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036074

Secondary Accession Numbers

HMDB36074

Metabolite Identification

Common Name

Tenuazonic acid

Description

Tenuazonic acid, also known as tenuazonate or acid, tenuazonic, belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. Based on a literature review very few articles have been published on Tenuazonic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0036074
     RDKit          3D
Tenuazonic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5016    2.0511    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6403    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -0.3076    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.6746   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0465   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671    1.3109   -0.4779 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752    1.0990   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    2.0287    0.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -0.3253   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1235   -0.9666   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944   -0.1318    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.1961   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -0.9323   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -2.3354   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4542    2.3910    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4611    2.7392   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    2.2032    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    0.6967   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275    0.2282    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.3304    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6521   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -2.5036    0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484   -1.7319    0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.0405   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    2.3036   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023    0.2016    1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -0.6422    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127    0.7856   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.9554   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  2  0
 13 14  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
M  END


  Mrv0541 02241215302D          

 14 14  0  0  0  0            999 V2000
    1.9804   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -1.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475   -0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    0.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1546   -1.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775   -0.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    1.0311    0.0000 O   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
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036074

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C1NC(=O)C(C(C)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)

> <INCHI_KEY>
CEIZFXOZIQNICU-UHFFFAOYSA-N

> <FORMULA>
C10H15NO3

> <MOLECULAR_WEIGHT>
197.231

> <EXACT_MASS>
197.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.60632372310234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.5687822743333341

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.049430920367062

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8067589277166642

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5461083056826469

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
52.73030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-acetyl-4-hydroxy-5-(sec-butyl)-1,5-dihydropyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036074
     RDKit          3D
Tenuazonic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5016    2.0511    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6403    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -0.3076    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.6746   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0465   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671    1.3109   -0.4779 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752    1.0990   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    2.0287    0.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -0.3253   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1235   -0.9666   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944   -0.1318    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.1961   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -0.9323   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -2.3354   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4542    2.3910    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4611    2.7392   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    2.2032    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    0.6967   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275    0.2282    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.3304    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6521   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -2.5036    0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484   -1.7319    0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.0405   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    2.3036   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023    0.2016    1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -0.6422    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127    0.7856   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.9554   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  2  0
 13 14  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.697  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.926   0.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.697   1.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.926   3.003   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.923  -2.541   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.462  -1.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.386   0.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.462   1.463   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -2.155  -3.003   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.310  -1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.697  -0.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.078  -0.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.078   1.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.310   1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   12                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7   13                                                       
CONECT    9   10                                                            
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12    6   10   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0036074
HETATM    1  C1  UNL     1      -2.502   2.051   0.483  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.706   0.640   0.063  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.569  -0.308   0.220  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.127  -1.675  -0.241  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.413   0.047  -0.689  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.167   1.311  -0.478  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.575   1.099  -0.227  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.399   2.029   0.018  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.799  -0.325  -0.316  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.124  -0.967  -0.127  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.294  -0.132   0.169  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.251  -2.196  -0.215  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.669  -0.932  -0.583  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.591  -2.335  -0.732  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.454   2.391   1.016  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.461   2.739  -0.381  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.702   2.203   1.240  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.045   0.697  -1.025  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.628   0.228   0.602  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.221  -0.330   1.246  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.119  -1.652  -1.330  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.555  -2.504   0.177  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.148  -1.732   0.188  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.773  -0.040  -1.782  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.241   2.304  -0.498  1.00  0.00           H  
HETATM   26  H12 UNL     1       4.202   0.202   1.237  1.00  0.00           H  
HETATM   27  H13 UNL     1       5.250  -0.642   0.029  1.00  0.00           H  
HETATM   28  H14 UNL     1       4.313   0.786  -0.481  1.00  0.00           H  
HETATM   29  H15 UNL     1       1.030  -2.955  -0.060  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4    5   20
CONECT    4   21   22   23
CONECT    5    6   13   24
CONECT    6    7   25
CONECT    7    8    8    9
CONECT    9   10   13   13
CONECT   10   11   12   12
CONECT   11   26   27   28
CONECT   13   14
CONECT   14   29
END

HMDB0036074
     RDKit          3D
Tenuazonic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5016    2.0511    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6403    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -0.3076    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.6746   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0465   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671    1.3109   -0.4779 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752    1.0990   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    2.0287    0.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -0.3253   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1235   -0.9666   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944   -0.1318    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.1961   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -0.9323   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -2.3354   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4542    2.3910    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4611    2.7392   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    2.2032    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    0.6967   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275    0.2282    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.3304    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6521   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -2.5036    0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484   -1.7319    0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.0405   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    2.3036   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023    0.2016    1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -0.6422    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127    0.7856   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.9554   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  2  0
 13 14  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tenuazonate	Generator
Acid, tenuazonic	MeSH
3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9ci	HMDB
3-Acetyl-5-sec-butyl-4-hydroxy-L-3-pyrrolin-2-one	HMDB
3-Acetyl-5-sec-butyl-pyrrole-2,4-diol	HMDB
3-Acetyl-5-sec-butyltetramic acid	HMDB
L-Tenuazonic acid	HMDB
Vivotoxin	HMDB
Tenuazonic acid	MeSH

Chemical Formula

C₁₀H₁₅NO₃

Average Molecular Weight

197.231

Monoisotopic Molecular Weight

197.105193351

IUPAC Name

3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

3-acetyl-4-hydroxy-5-(sec-butyl)-1,5-dihydropyrrol-2-one

CAS Registry Number

610-88-8

SMILES

CCC(C)C1NC(=O)C(C(C)=O)=C1O

InChI Identifier

InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)

InChI Key

CEIZFXOZIQNICU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036074)
Cytoplasm (HMDB: HMDB0036074)

Source

Exogenous

Food

Food (HMDB: HMDB0036074)

Not Available

Nutrient (HMDB: HMDB0036074)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 - 75.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.6 g/L	ALOGPS
logP	0.17	ALOGPS
logP	0.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.73 m³·mol⁻¹	ChemAxon
Polarizability	20.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.849	30932474
DeepCCS	[M-H]-	145.048	30932474
DeepCCS	[M-2H]-	180.51	30932474
DeepCCS	[M+Na]+	156.283	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	139.8	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	146.5	32859911
AllCCS	[M+HCOO]-	147.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tenuazonic acid	CCC(C)C1NC(=O)C(C(C)=O)=C1O	2491.9	Standard polar	33892256
Tenuazonic acid	CCC(C)C1NC(=O)C(C(C)=O)=C1O	1608.4	Standard non polar	33892256
Tenuazonic acid	CCC(C)C1NC(=O)C(C(C)=O)=C1O	1620.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tenuazonic acid,1TMS,isomer #1	CCC(C)C1NC(=O)C(C(C)=O)=C1O[Si](C)(C)C	1718.8	Semi standard non polar	33892256
Tenuazonic acid,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=C(O)C(C(C)CC)NC1=O	1766.0	Semi standard non polar	33892256
Tenuazonic acid,1TMS,isomer #3	CCC(C)C1C(O)=C(C(C)=O)C(=O)N1[Si](C)(C)C	1625.5	Semi standard non polar	33892256
Tenuazonic acid,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C(C)CC)NC1=O	1882.7	Semi standard non polar	33892256
Tenuazonic acid,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C(C)CC)NC1=O	1784.2	Standard non polar	33892256
Tenuazonic acid,2TMS,isomer #2	CCC(C)C1C(O[Si](C)(C)C)=C(C(C)=O)C(=O)N1[Si](C)(C)C	1723.8	Semi standard non polar	33892256
Tenuazonic acid,2TMS,isomer #2	CCC(C)C1C(O[Si](C)(C)C)=C(C(C)=O)C(=O)N1[Si](C)(C)C	1751.8	Standard non polar	33892256
Tenuazonic acid,2TMS,isomer #3	C=C(O[Si](C)(C)C)C1=C(O)C(C(C)CC)N([Si](C)(C)C)C1=O	1785.4	Semi standard non polar	33892256
Tenuazonic acid,2TMS,isomer #3	C=C(O[Si](C)(C)C)C1=C(O)C(C(C)CC)N([Si](C)(C)C)C1=O	1784.7	Standard non polar	33892256
Tenuazonic acid,3TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C(C)CC)N([Si](C)(C)C)C1=O	1852.5	Semi standard non polar	33892256
Tenuazonic acid,3TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C(C)CC)N([Si](C)(C)C)C1=O	1881.2	Standard non polar	33892256
Tenuazonic acid,1TBDMS,isomer #1	CCC(C)C1NC(=O)C(C(C)=O)=C1O[Si](C)(C)C(C)(C)C	1946.3	Semi standard non polar	33892256
Tenuazonic acid,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(C(C)CC)NC1=O	1990.8	Semi standard non polar	33892256
Tenuazonic acid,1TBDMS,isomer #3	CCC(C)C1C(O)=C(C(C)=O)C(=O)N1[Si](C)(C)C(C)(C)C	1854.5	Semi standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C(C)CC)NC1=O	2299.7	Semi standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C(C)CC)NC1=O	2193.2	Standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #2	CCC(C)C1C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(=O)N1[Si](C)(C)C(C)(C)C	2153.2	Semi standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #2	CCC(C)C1C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(=O)N1[Si](C)(C)C(C)(C)C	2162.2	Standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(C(C)CC)N([Si](C)(C)C(C)(C)C)C1=O	2212.7	Semi standard non polar	33892256
Tenuazonic acid,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(C(C)CC)N([Si](C)(C)C(C)(C)C)C1=O	2175.9	Standard non polar	33892256
Tenuazonic acid,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C(C)CC)N([Si](C)(C)C(C)(C)C)C1=O	2460.6	Semi standard non polar	33892256
Tenuazonic acid,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C(C)CC)N([Si](C)(C)C(C)(C)C)C1=O	2420.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tenuazonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-bcfb00cf6a866cab84f3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenuazonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0ffx-9220000000-3efe8522a8334eb2c562	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenuazonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenuazonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenuazonic acid 10V, Negative-QTOF	splash10-0002-0900000000-19a6160a2f4eb732a5c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenuazonic acid 20V, Negative-QTOF	splash10-03di-0900000000-cb450a2563e6af57c58b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenuazonic acid 40V, Negative-QTOF	splash10-03di-0900000000-b84d2936dae91e688ba7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 10V, Positive-QTOF	splash10-0002-0900000000-c05c5e4cffa5cbca5423	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 20V, Positive-QTOF	splash10-000w-2900000000-347b74f895c5fbe86394	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 40V, Positive-QTOF	splash10-066r-9100000000-9235d19135d7b87978cf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 10V, Negative-QTOF	splash10-0f6t-0900000000-e4443634dd422a7ba52c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 20V, Negative-QTOF	splash10-0udi-2900000000-896a08a45cd2007229ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 40V, Negative-QTOF	splash10-000x-9100000000-5051d66e608a659ec7f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 10V, Negative-QTOF	splash10-0002-0900000000-dc55dda2e38219c36c8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 20V, Negative-QTOF	splash10-0002-0900000000-f949413f6412b576dcf8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 40V, Negative-QTOF	splash10-0006-9300000000-1bb6bae63d8eac08d4e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 10V, Positive-QTOF	splash10-0002-0900000000-cc94bcc041f6d746620e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 20V, Positive-QTOF	splash10-0005-2900000000-04182e6f71ae7ad3c846	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenuazonic acid 40V, Positive-QTOF	splash10-0006-9100000000-d840225406cdc8dbb01a	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tenuazonic acid

METLIN ID

Not Available

PubChem Compound

54678599

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Tenuazonic acid (HMDB0036074)

MOL for HMDB0036074 (Tenuazonic acid)

3D MOL for HMDB0036074 (Tenuazonic acid)

3D SDF for HMDB0036074 (Tenuazonic acid)

3D-SDF for HMDB0036074 (Tenuazonic acid)

PDB for HMDB0036074 (Tenuazonic acid)

3D PDB for HMDB0036074 (Tenuazonic acid)

SMILES for HMDB0036074 (Tenuazonic acid)

INCHI for HMDB0036074 (Tenuazonic acid)

Structure for HMDB0036074 (Tenuazonic acid)

3D Structure for HMDB0036074 (Tenuazonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra