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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:16 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036688

Secondary Accession Numbers

HMDB36688

Metabolite Identification

Common Name

Costunolide

Description

Costunolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Costunolide.

Structure

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

HMDB0036688
     RDKit          3D
Costunolide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.7849    3.3424    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464    2.4499   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8982   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9482    2.3121   -1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    0.8214   -1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688    0.4432   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236   -0.3478   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5937   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -2.2213    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -2.3205   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -2.1968   -0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053   -1.7274    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   -0.4404    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    0.0125    2.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285    0.5586   -0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    1.5815    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    1.7875   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    3.6823    0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352    3.7522    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.0093   -2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    0.1775    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.4465    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -2.7979    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -2.9044    1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -3.4140   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -2.0183   -2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8115   -3.2521   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.6868   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -2.4374    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713   -0.8258    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.8347    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.4376    1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.1913   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792    1.1532   -0.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    1.2763    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    2.5819    0.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604    2.3462   -1.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END


  Mrv0541 05061309162D          

 17 18  0  0  0  0            999 V2000
    2.9610    3.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1447    3.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  2  0  0  0  0
 10  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  3  2  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036688

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9-

> <INCHI_KEY>
HRYLQFBHBWLLLL-GYIATTAWSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.375965883311586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
3.8161666466666664

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.874751124392721

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
69.9464

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036688
     RDKit          3D
Costunolide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.7849    3.3424    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464    2.4499   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8982   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9482    2.3121   -1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    0.8214   -1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688    0.4432   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236   -0.3478   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5937   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -2.2213    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -2.3205   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -2.1968   -0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053   -1.7274    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   -0.4404    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    0.0125    2.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285    0.5586   -0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    1.5815    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    1.7875   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    3.6823    0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352    3.7522    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.0093   -2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    0.1775    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.4465    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -2.7979    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -2.9044    1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -3.4140   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -2.0183   -2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8115   -3.2521   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.6868   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -2.4374    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713   -0.8258    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.8347    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.4376    1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.1913   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792    1.1532   -0.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    1.2763    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    2.5819    0.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604    2.3462   -1.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.527   6.570   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.328  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.270   5.690   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.833   0.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.198   4.151   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.530   3.849   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.682   1.820   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8   10                                                       
CONECT    8    7   13                                                       
CONECT    9   11   14                                                       
CONECT   10    1    5    7                                                  
CONECT   11    2    6    9                                                  
CONECT   12    3   13   15                                                  
CONECT   13    8   12   14                                                  
CONECT   14    9   13   17                                                  
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036688
HETATM    1  C1  UNL     1      -1.785   3.342   0.463  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.646   2.450  -0.488  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.756   1.898  -1.277  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.948   2.312  -1.321  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.248   0.821  -1.977  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.969   0.443  -1.445  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.224  -0.348  -0.243  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.845  -1.594  -0.042  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.206  -2.221   1.255  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.098  -2.321  -1.071  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.408  -2.197  -0.909  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.805  -1.727   0.416  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.913  -0.440   0.706  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.327   0.012   2.089  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.628   0.559  -0.320  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.594   1.581   0.115  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.431   1.787  -1.008  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.906   3.682   0.981  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.735   3.752   0.751  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.427  -0.009  -2.257  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.788   0.177   0.551  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.486  -1.446   2.018  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.145  -2.798   1.080  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.422  -2.904   1.635  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.402  -3.414  -1.038  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.439  -2.018  -2.088  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.812  -3.252  -1.013  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.895  -1.687  -1.769  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.029  -2.437   1.221  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.371  -0.826   2.784  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.671   0.835   2.448  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.356   0.438   1.976  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.352   0.191  -1.299  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.579   1.153  -0.477  1.00  0.00           H  
HETATM   35  H18 UNL     1       0.075   1.276   1.051  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.030   2.582   0.311  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.060   2.346  -1.806  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   17   20
CONECT    7    8    8   21
CONECT    8    9   10
CONECT    9   22   23   24
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   13   29
CONECT   13   14   15
CONECT   14   30   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   37
END

HMDB0036688
     RDKit          3D
Costunolide
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.7849    3.3424    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464    2.4499   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8982   -1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9482    2.3121   -1.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    0.8214   -1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688    0.4432   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236   -0.3478   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5937   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -2.2213    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -2.3205   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -2.1968   -0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053   -1.7274    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   -0.4404    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    0.0125    2.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285    0.5586   -0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    1.5815    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    1.7875   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    3.6823    0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352    3.7522    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.0093   -2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    0.1775    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.4465    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -2.7979    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -2.9044    1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -3.4140   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -2.0183   -2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8115   -3.2521   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.6868   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -2.4374    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713   -0.8258    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.8347    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    0.4376    1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.1913   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792    1.1532   -0.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    1.2763    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    2.5819    0.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604    2.3462   -1.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Costunlide	HMDB
Costunolid	HMDB
Costus lactone	HMDB
Isocostunolide	MeSH
Costunolide	MeSH

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

553-21-9

SMILES

C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1

InChI Identifier

InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9-

InChI Key

HRYLQFBHBWLLLL-GYIATTAWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036688)

Source

Endogenous

Endogenous (HMDB: HMDB0036688)

Plant

Plant (HMDB: HMDB0036688)

Animal

Animal (HMDB: HMDB0036688)

Exogenous

Food

Food (HMDB: HMDB0036688)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)
Tarragon (FooDB: FOOD00019)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036688)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036688)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036688)

Lipid metabolism pathway (HMDB: HMDB0036688)

Cellular process

Cell signaling (HMDB: HMDB0036688)

Biochemical process

Lipid transport (HMDB: HMDB0036688)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036688)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0036688)
Anticancer agent (HMDB: HMDB0036688)

Agriculture

Pesticide (HMDB: HMDB0036688)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 - 107 °C	Not Available
Boiling Point	205.00 to 211.00 °C. @ 13.00 mm Hg	The Good Scents Company Information System
Water Solubility	9.38 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.049 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.097 g/L	ALOGPS
logP	4.22	ALOGPS
logP	3.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.95 m³·mol⁻¹	ChemAxon
Polarizability	26.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.019	31661259
DarkChem	[M-H]-	150.57	31661259
DeepCCS	[M+H]+	161.461	30932474
DeepCCS	[M-H]-	159.103	30932474
DeepCCS	[M-2H]-	192.027	30932474
DeepCCS	[M+Na]+	167.554	30932474
AllCCS	[M+H]+	154.5	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	158.2	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	160.3	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.	7.52 minutes	32390414
Predicted by Siyang on May 30, 2022	17.3344 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2805.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	517.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	297.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	123.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	589.3 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	786.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1544.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	531.6 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	1243.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	407.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	521.4 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	11.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Costunolide	C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1	2485.0	Standard polar	33892256
Costunolide	C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1	1854.9	Standard non polar	33892256
Costunolide	C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1	1998.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Costunolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4920000000-4e64fd5fdc43499db09c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Costunolide 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 - Costunolide 10V, Positive-QTOF	splash10-001i-0390000000-90b5c48b328b46f82204	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOF	splash10-01qi-1930000000-6cfdc6b5c84eab2f9f7d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOF	splash10-0mi6-9710000000-ddda69ef8cc562458ad9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOF	splash10-001i-0290000000-07ab038b28845f8d64a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOF	splash10-001r-0790000000-f2b3e216b0db2d7a4dca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOF	splash10-000i-5900000000-157775eb321e2f75fa2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOF	splash10-001i-0390000000-16fbf014b5978f284c85	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOF	splash10-01b9-9500000000-2ce7ff1d0912ac2d90ee	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 10V, Positive-QTOF	splash10-001i-0190000000-c5e9a61d3011edbf30f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOF	splash10-001r-0980000000-0a8be66862e84091d6a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOF	splash10-0a4i-0900000000-9eaa625d0c4efee67791	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

Costunolide

METLIN ID

Not Available

PubChem Compound

5367559

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1016401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lee MG, Lee KT, Chi SG, Park JH: Costunolide induces apoptosis by ROS-mediated mitochondrial permeability transition and cytochrome C release. Biol Pharm Bull. 2001 Mar;24(3):303-6. [PubMed:11256490 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Costunolide (HMDB0036688)

MOL for HMDB0036688 (Costunolide)

3D MOL for HMDB0036688 (Costunolide)

3D SDF for HMDB0036688 (Costunolide)

3D-SDF for HMDB0036688 (Costunolide)

PDB for HMDB0036688 (Costunolide)

3D PDB for HMDB0036688 (Costunolide)

SMILES for HMDB0036688 (Costunolide)

INCHI for HMDB0036688 (Costunolide)

Structure for HMDB0036688 (Costunolide)

3D Structure for HMDB0036688 (Costunolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra