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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015168

Secondary Accession Numbers

HMDB15168

Metabolite Identification

Common Name

Cerulenin

Description

Cerulenin belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof). At an intraperitoneal dose of 30 milligrams per kilogram, it has been shown to inhibit feeding and induce dramatic weight loss in mice by a mechanism similar to, but independent or downstream of, leptin signaling. Cerulenin is a drug which is used for use as a biochemical tool, cerulenin is shown to cause dramatic weight loss in animals. Cerulenin is an antifungal antibiotic that inhibits fatty acid and steroid biosynthesis. Cerulenin is an extremely weak basic (essentially neutral) compound (based on its pKa). Cerulenin is a potentially toxic compound. Inhibition involves covalent thioacylation that permanently inactivates the enzymes. These two behaviors may increase the availability of energy in the form of ATP, perhaps sensed by AMPK, in the hypothalamus. It is found naturally in the industrial strain Cephalosporium caerulens (Sarocladium oryzae, the sheath rot pathogen of rice). In sterol synthesis, cerulenin inhibits HMG-CoA synthetase activity. But in general conclusion, cerulenin has inhibitory effects on sterol synthesis. It also has the related activity of stimulating fatty acid oxidation through the activation of CPT1, another enzyme normally inhibited by malonyl-CoA. Cerulenin causes a dose-dependent decrease in HER2/neu protein levels in breast cancer cells, from 14% at 1.25 to 78% at 10 milligrams per liter, and targeting of fatty acid synthase by related drugs has been suggested as a possible treatment. In fatty acid synthesis, it has been reported to bind in equimolar ratio to b-keto-acyl-ACP synthase, one of the seven moieties of fatty acid synthase, blocking the interaction of malonyl-CoA. It was also reported that cerulenin specifically inhibited fatty acid biosynthesis in Saccharomyces cerevisiae without having an effect on sterol formation.

Structure

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

HMDB0015168
     RDKit          3D
Cerulenin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.9316    1.7638    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    1.4728   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    1.1392    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3016    0.8473   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -0.5161   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383   -0.7228    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -2.1016    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595   -2.3111   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.3630    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -0.6229    1.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.3522   -0.2184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5486   -1.4207    0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5460   -0.3672   -0.0553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3074    1.0124    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    2.0469   -0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339    1.3572    1.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    2.7822   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8040    1.7233    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.9730   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662    1.5322   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635    1.0805    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.9400   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.5746   -0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964   -1.3648   -0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0661    0.1458    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210   -2.1861    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685   -2.8684    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -2.0591   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -3.3589   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539   -2.1229   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -0.4772   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024    3.0340   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    1.7901   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  6
 13 31  1  6
 15 32  1  0
 15 33  1  0
M  END

1034
  Mrv0541 02231215112D          

 16 16  0  0  1  0            999 V2000
    3.9345    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0615   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.2615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    0.2615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    0.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0615   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2050    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9194   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6339    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0629    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7774   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  9  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  6  9  1  6  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  3  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  3  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015168

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/t10-,11-/m1/s1

> <INCHI_KEY>
GVEZIHKRYBHEFX-GHMZBOCLSA-N

> <FORMULA>
C12H17NO3

> <MOLECULAR_WEIGHT>
223.2683

> <EXACT_MASS>
223.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.901511054240988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.4996911163333335

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.68536616192688

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.15640801160168

> <JCHEM_PKA_STRONGEST_BASIC>
-4.324867253494774

> <JCHEM_POLAR_SURFACE_AREA>
72.69

> <JCHEM_REFRACTIVITY>
62.5427

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cerulenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015168
     RDKit          3D
Cerulenin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.9316    1.7638    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    1.4728   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    1.1392    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3016    0.8473   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -0.5161   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383   -0.7228    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -2.1016    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595   -2.3111   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.3630    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -0.6229    1.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.3522   -0.2184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5486   -1.4207    0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5460   -0.3672   -0.0553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3074    1.0124    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    2.0469   -0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339    1.3572    1.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    2.7822   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8040    1.7233    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.9730   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662    1.5322   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635    1.0805    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.9400   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.5746   -0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964   -1.3648   -0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0661    0.1458    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210   -2.1861    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685   -2.8684    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -2.0591   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -3.3589   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539   -2.1229   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -0.4772   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024    3.0340   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    1.7901   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  6
 13 31  1  6
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1034                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.344   1.822   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.448  -1.822   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241  -1.822   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.907   0.488   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.114   0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574   0.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.448  -0.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.782   0.488   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241  -0.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.116  -0.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.449   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.783  -0.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.117   0.488   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.450  -0.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.784   0.488   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.118  -0.282   0.000  0.00  0.00           C+0
CONECT    1    5    6                                                       
CONECT    2    7                                                            
CONECT    3    9                                                            
CONECT    4    9                                                            
CONECT    5    1    6    7                                                  
CONECT    6    1    5    9                                                  
CONECT    7    2    5    8                                                  
CONECT    8    7   10                                                       
CONECT    9    3    4    6                                                  
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0015168
HETATM    1  C1  UNL     1       5.932   1.764   0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.644   1.473  -0.597  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.587   1.139   0.127  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.302   0.847  -0.533  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.809  -0.516  -0.275  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.638  -0.723   0.320  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.139  -2.102   0.581  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.159  -2.311  -0.127  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.188  -1.363   0.400  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.921  -0.623   1.319  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.516  -1.352  -0.218  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.549  -1.421   0.837  1.00  0.00           O  
HETATM   13  C11 UNL     1      -4.546  -0.367  -0.055  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.307   1.012   0.365  1.00  0.00           C  
HETATM   15  N1  UNL     1      -5.153   2.047  -0.217  1.00  0.00           N  
HETATM   16  O3  UNL     1      -3.434   1.357   1.183  1.00  0.00           O  
HETATM   17  H1  UNL     1       6.307   2.782  -0.159  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.804   1.723   1.176  1.00  0.00           H  
HETATM   19  H3  UNL     1       6.674   0.973  -0.189  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.566   1.532  -1.683  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.663   1.080   1.202  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.404   0.940  -1.652  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.507   1.575  -0.260  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.396  -1.365  -0.568  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.066   0.146   0.607  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.021  -2.186   1.686  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.869  -2.868   0.255  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.033  -2.059  -1.216  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.511  -3.359  -0.105  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.654  -2.123  -1.027  1.00  0.00           H  
HETATM   31  H15 UNL     1      -5.423  -0.477  -0.797  1.00  0.00           H  
HETATM   32  H16 UNL     1      -4.802   3.034  -0.283  1.00  0.00           H  
HETATM   33  H17 UNL     1      -6.089   1.790  -0.556  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   20
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   10   11
CONECT   11   12   13   30
CONECT   12   13
CONECT   13   14   31
CONECT   14   15   16   16
CONECT   15   32   33
END

HMDB0015168
     RDKit          3D
Cerulenin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.9316    1.7638    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    1.4728   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    1.1392    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3016    0.8473   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -0.5161   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383   -0.7228    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -2.1016    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595   -2.3111   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.3630    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -0.6229    1.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.3522   -0.2184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5486   -1.4207    0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5460   -0.3672   -0.0553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3074    1.0124    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    2.0469   -0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339    1.3572    1.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    2.7822   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8040    1.7233    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.9730   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662    1.5322   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635    1.0805    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.9400   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.5746   -0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964   -1.3648   -0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0661    0.1458    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210   -2.1861    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685   -2.8684    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -2.0591   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -3.3589   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539   -2.1229   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -0.4772   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024    3.0340   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    1.7901   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  6
 13 31  1  6
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,3S)-3-(Nona-4,7-dienoyl)oxirane-2-carboximidate	HMDB

Chemical Formula

C₁₂H₁₇NO₃

Average Molecular Weight

223.2683

Monoisotopic Molecular Weight

223.120843415

IUPAC Name

(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide

Traditional Name

cerulenin

CAS Registry Number

17397-89-6

SMILES

CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O

InChI Identifier

InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/t10-,11-/m1/s1

InChI Key

GVEZIHKRYBHEFX-GHMZBOCLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Oxirane carboxylic acids and derivatives

Direct Parent

Oxirane carboxylic acids and derivatives

Alternative Parents

Substituents

Oxirane carboxylic acid or derivatives
Monosaccharide
Carboxamide group
Ketone
Primary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015168)
Extracellular (HMDB: HMDB0015168)

Source

Exogenous

Exogenous (HMDB: HMDB0015168)

Process

Not Available

Role

Industrial application

Antifungal agent (HMDB: HMDB0015168)
Antiinfective agent (HMDB: HMDB0015168)

Pharmaceutical industry

Antilipemic drug (HMDB: HMDB0015168)

Antimicrobial agent

Antibiotic (HMDB: HMDB0015168)

Biological role

Antimetabolite (HMDB: HMDB0015168)

Modulator

Inhibitor

Fatty acid synthesis inhibitor (HMDB: HMDB0015168)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.6 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.6 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.5	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	62.54 m³·mol⁻¹	ChemAxon
Polarizability	23.9 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
DarkChem	[M+H]+	157.873	31661259
DarkChem	[M-H]-	156.459	31661259
DeepCCS	[M+H]+	153.464	30932474
DeepCCS	[M-H]-	151.106	30932474
DeepCCS	[M-2H]-	184.586	30932474
DeepCCS	[M+Na]+	160.173	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.6	32859911
AllCCS	[M+NH4]+	158.8	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	156.0	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.48 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4667 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.55 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2178.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	208.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	441.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	392.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1110.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	416.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1078.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	218.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cerulenin	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O	2841.7	Standard polar	33892256
Cerulenin	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O	1794.5	Standard non polar	33892256
Cerulenin	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O	1956.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cerulenin,1TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O	1923.7	Semi standard non polar	33892256
Cerulenin,1TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O	1835.2	Standard non polar	33892256
Cerulenin,1TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O	2847.3	Standard polar	33892256
Cerulenin,1TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O	1946.4	Semi standard non polar	33892256
Cerulenin,1TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O	1767.1	Standard non polar	33892256
Cerulenin,1TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O	2860.6	Standard polar	33892256
Cerulenin,1TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	1874.0	Semi standard non polar	33892256
Cerulenin,1TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	1886.5	Standard non polar	33892256
Cerulenin,1TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	2553.9	Standard polar	33892256
Cerulenin,2TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C	1955.6	Semi standard non polar	33892256
Cerulenin,2TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C	2022.9	Standard non polar	33892256
Cerulenin,2TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C	2363.5	Standard polar	33892256
Cerulenin,2TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	2002.0	Semi standard non polar	33892256
Cerulenin,2TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	1992.4	Standard non polar	33892256
Cerulenin,2TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C	2417.1	Standard polar	33892256
Cerulenin,2TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2006.2	Semi standard non polar	33892256
Cerulenin,2TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2066.1	Standard non polar	33892256
Cerulenin,2TMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2318.7	Standard polar	33892256
Cerulenin,3TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2058.0	Semi standard non polar	33892256
Cerulenin,3TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2138.5	Standard non polar	33892256
Cerulenin,3TMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2164.2	Standard polar	33892256
Cerulenin,3TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2096.7	Semi standard non polar	33892256
Cerulenin,3TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2142.4	Standard non polar	33892256
Cerulenin,3TMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C	2227.3	Standard polar	33892256
Cerulenin,1TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O	2166.3	Semi standard non polar	33892256
Cerulenin,1TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O	2042.9	Standard non polar	33892256
Cerulenin,1TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O	2905.4	Standard polar	33892256
Cerulenin,1TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O	2184.3	Semi standard non polar	33892256
Cerulenin,1TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O	1958.6	Standard non polar	33892256
Cerulenin,1TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O	2919.1	Standard polar	33892256
Cerulenin,1TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2092.9	Semi standard non polar	33892256
Cerulenin,1TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2101.5	Standard non polar	33892256
Cerulenin,1TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2587.9	Standard polar	33892256
Cerulenin,2TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2392.0	Semi standard non polar	33892256
Cerulenin,2TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2393.2	Standard non polar	33892256
Cerulenin,2TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2517.7	Standard polar	33892256
Cerulenin,2TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2435.3	Semi standard non polar	33892256
Cerulenin,2TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2346.6	Standard non polar	33892256
Cerulenin,2TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C	2553.3	Standard polar	33892256
Cerulenin,2TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2439.2	Semi standard non polar	33892256
Cerulenin,2TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2464.9	Standard non polar	33892256
Cerulenin,2TBDMS,isomer #3	CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2435.2	Standard polar	33892256
Cerulenin,3TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2700.4	Semi standard non polar	33892256
Cerulenin,3TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2639.1	Standard non polar	33892256
Cerulenin,3TBDMS,isomer #1	CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2400.1	Standard polar	33892256
Cerulenin,3TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2734.5	Semi standard non polar	33892256
Cerulenin,3TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2676.0	Standard non polar	33892256
Cerulenin,3TBDMS,isomer #2	CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2419.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cerulenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-06rf-9600000000-ac88ca6a297eb89d73b4	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cerulenin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 10V, Positive-QTOF	splash10-05fr-1290000000-202e41a2408ad9df3f62	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 20V, Positive-QTOF	splash10-0a4r-8950000000-c0265c2ede42a8a7b944	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 40V, Positive-QTOF	splash10-0frf-9100000000-c8d70361d98f08b9775a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 10V, Negative-QTOF	splash10-00di-4490000000-130e0abcad17614007d8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 20V, Negative-QTOF	splash10-0570-9830000000-b6afbfbbfa11b458c4ba	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 40V, Negative-QTOF	splash10-0006-9000000000-289b3846b10b0578e10f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 10V, Positive-QTOF	splash10-05fr-6970000000-a192a4a992558941f3f0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 20V, Positive-QTOF	splash10-014i-9400000000-f684bf91e79510c00ed8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 40V, Positive-QTOF	splash10-014i-9200000000-91ff9f0cebc2d5a63e30	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 10V, Negative-QTOF	splash10-00dl-6290000000-dc435b26c818bc2f0134	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 20V, Negative-QTOF	splash10-0006-9100000000-ac3aa58779f68cf0a799	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerulenin 40V, Negative-QTOF	splash10-0006-9000000000-79c001be721cdc21c374	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01034	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01034	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01034

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445281

KEGG Compound ID

C12058

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cerulenin

METLIN ID

Not Available

PubChem Compound

5282054

PDB ID

Not Available

ChEBI ID

171741

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

Straub SG, Yajima H, Komatsu M, Aizawa T, Sharp GW: The effects of cerulenin, an inhibitor of protein acylation, on the two phases of glucose-stimulated insulin secretion. Diabetes. 2002 Feb;51 Suppl 1:S91-5. [PubMed:11815464 ]
Huang P, Zhu S, Lu S, Dai Z, Jin Y: [An experimental study on cerulenin induced apoptosis of human colonic cancer cells]. Zhonghua Bing Li Xue Za Zhi. 2000 Apr;29(2):115-8. [PubMed:11866903 ]

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

References

Oskouian B, Saba JD: YAP1 confers resistance to the fatty acid synthase inhibitor cerulenin through the transporter Flr1p in Saccharomyces cerevisiae. Mol Gen Genet. 1999 Mar;261(2):346-53. [PubMed:10102370 ]
Li JN, Gorospe M, Chrest FJ, Kumaravel TS, Evans MK, Han WF, Pizer ES: Pharmacological inhibition of fatty acid synthase activity produces both cytostatic and cytotoxic effects modulated by p53. Cancer Res. 2001 Feb 15;61(4):1493-9. [PubMed:11245456 ]
Heiligtag SJ, Bredehorst R, David KA: Key role of mitochondria in cerulenin-mediated apoptosis. Cell Death Differ. 2002 Sep;9(9):1017-25. [PubMed:12181752 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Flavin R, Peluso S, Nguyen PL, Loda M: Fatty acid synthase as a potential therapeutic target in cancer. Future Oncol. 2010 Apr;6(4):551-62. doi: 10.2217/fon.10.11. [PubMed:20373869 ]
Lupu R, Menendez JA: Pharmacological inhibitors of Fatty Acid Synthase (FASN)--catalyzed endogenous fatty acid biogenesis: a new family of anti-cancer agents? Curr Pharm Biotechnol. 2006 Dec;7(6):483-93. [PubMed:17168665 ]
Ronnett GV, Kim EK, Landree LE, Tu Y: Fatty acid metabolism as a target for obesity treatment. Physiol Behav. 2005 May 19;85(1):25-35. [PubMed:15878185 ]

Showing metabocard for Cerulenin (HMDB0015168)

MOL for HMDB0015168 (Cerulenin)

3D MOL for HMDB0015168 (Cerulenin)

3D SDF for HMDB0015168 (Cerulenin)

3D-SDF for HMDB0015168 (Cerulenin)

PDB for HMDB0015168 (Cerulenin)

3D PDB for HMDB0015168 (Cerulenin)

SMILES for HMDB0015168 (Cerulenin)

INCHI for HMDB0015168 (Cerulenin)

Structure for HMDB0015168 (Cerulenin)

3D Structure for HMDB0015168 (Cerulenin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References