Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:55:03 UTC

Update Date

2021-09-23 19:55:09 UTC

HMDB ID

HMDB0302703

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Eremanthin

Description

Eremanthin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Eremanthin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Eremanthin can be found in sweet bay, which makes eremanthin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302703
     RDKit          3D
Eremanthin
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0424   -0.9222   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -0.1457    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    1.3006   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    2.0337   -0.3376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407    1.7345    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.6637   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6088   -0.5619    0.2680 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2261   -1.6583   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554   -2.1128   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -1.5168   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.3708   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035   -0.2236    0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3145    0.7130   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    1.9347    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    2.0327    0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    3.1242    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    0.6522    0.8163 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0378   -0.5149   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.9959    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449    0.5729   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -0.8509    1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.3918   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8897   -2.5424   -0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -3.1345   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112   -3.2010   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030   -2.8461    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3782   -1.7939   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -0.3636    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    0.2975   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.9913   -1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.6740    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.8356   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613    3.1135    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    4.0685    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    0.4046    1.8305 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  1
  8 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
M  END


  Mrv0541 02241221482D          

 17 19  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  1  0  0  0
 11 12  2  0  0  0  0
  6 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  1  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302703

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC[C@@H]2[C@H](OC(=O)C2=C)[C@@H]2[C@H]1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h4,11-14H,2-3,5-7H2,1H3/t11-,12-,13-,14-/m0/s1

> <INCHI_KEY>
BWRZDLYJNURUHS-XUXIUFHCSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.3022

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.90219672453718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aR,9aR,9bS)-6-methyl-3,9-dimethylidene-2H,3H,3aH,4H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
3.017321547

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.866616846188646

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.0439

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eremanthin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302703
     RDKit          3D
Eremanthin
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0424   -0.9222   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -0.1457    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    1.3006   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    2.0337   -0.3376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407    1.7345    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.6637   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6088   -0.5619    0.2680 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2261   -1.6583   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554   -2.1128   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -1.5168   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.3708   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035   -0.2236    0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3145    0.7130   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    1.9347    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    2.0327    0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    3.1242    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    0.6522    0.8163 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0378   -0.5149   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.9959    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449    0.5729   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -0.8509    1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.3918   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8897   -2.5424   -0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -3.1345   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112   -3.2010   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030   -2.8461    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3782   -1.7939   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -0.3636    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    0.2975   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.9913   -1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.6740    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.8356   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613    3.1135    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    4.0685    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    0.4046    1.8305 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  1
  8 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
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       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.380  -2.160   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0302703
HETATM    1  C1  UNL     1       4.042  -0.922  -0.014  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.986  -0.146   0.041  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.975   1.301  -0.114  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.953   2.034  -0.338  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.641   1.735   0.037  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.770   0.664  -0.127  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.609  -0.562   0.268  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.226  -1.658  -0.647  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.155  -2.113  -0.586  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.247  -1.517  -0.148  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.465  -2.371  -0.278  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.503  -0.224   0.425  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.315   0.713  -0.484  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.380   1.935   0.408  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.978   2.033   0.892  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.365   3.124   1.308  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.394   0.652   0.816  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.038  -0.515  -0.189  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.002  -1.996   0.108  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.445   0.573  -1.197  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.433  -0.851   1.319  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.519  -1.392  -1.705  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.890  -2.542  -0.411  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.289  -3.134  -0.978  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.311  -3.201  -0.985  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.603  -2.846   0.737  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.378  -1.794  -0.462  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.173  -0.364   1.326  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.286   0.297  -0.737  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.705   0.991  -1.379  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.006   1.674   1.270  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.714   2.836  -0.132  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.661   3.114   1.646  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.875   4.068   1.323  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.047   0.405   1.831  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   17   20
CONECT    7    8   21
CONECT    8    9   22   23
CONECT    9   10   10   24
CONECT   10   11   12
CONECT   11   25   26   27
CONECT   12   13   17   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   16   17
CONECT   16   33   34
CONECT   17   35
END

HMDB0302703
     RDKit          3D
Eremanthin
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0424   -0.9222   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -0.1457    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    1.3006   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    2.0337   -0.3376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407    1.7345    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.6637   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6088   -0.5619    0.2680 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2261   -1.6583   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554   -2.1128   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -1.5168   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.3708   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035   -0.2236    0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3145    0.7130   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    1.9347    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    2.0327    0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    3.1242    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    0.6522    0.8163 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0378   -0.5149   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.9959    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449    0.5729   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -0.8509    1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.3918   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8897   -2.5424   -0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -3.1345   -0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112   -3.2010   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030   -2.8461    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3782   -1.7939   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -0.3636    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    0.2975   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    0.9913   -1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.6740    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.8356   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613    3.1135    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8752    4.0685    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    0.4046    1.8305 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  6
  7 21  1  1
  8 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Eremanthine	MeSH

Chemical Formula

C₁₅H₁₈O₂

Average Molecular Weight

230.3022

Monoisotopic Molecular Weight

230.13067982

IUPAC Name

(3aS,6aR,9aR,9bS)-6-methyl-3,9-dimethylidene-2H,3H,3aH,4H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

eremanthin

CAS Registry Number

Not Available

SMILES

CC1=CC[C@@H]2[C@H](OC(=O)C2=C)[C@@H]2[C@H]1CCC2=C

InChI Identifier

InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h4,11-14H,2-3,5-7H2,1H3/t11-,12-,13-,14-/m0/s1

InChI Key

BWRZDLYJNURUHS-XUXIUFHCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane 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

sesquiterpene lactone (CHEBI:4815 )
Guaianolide (C09406 )

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

allergen (HMDB: HMDB0302703)
schistosomicide (HMDB: HMDB0302703)

Industrial application

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0302703)
protisticide (HMDB: HMDB0302703)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.43	ALOGPS
logP	3.02	ChemAxon
logS	-3.1	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	67.04 m³·mol⁻¹	ChemAxon
Polarizability	25.9 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	154.027	32859911
AllCCS	[M+H-H2O]+	150.126	32859911
AllCCS	[M+Na]+	158.699	32859911
AllCCS	[M+NH4]+	157.654	32859911
AllCCS	[M-H]-	159.185	32859911
AllCCS	[M+Na-2H]-	159.038	32859911
AllCCS	[M+HCOO]-	158.985	32859911
DeepCCS	[M+H]+	159.921	30932474
DeepCCS	[M-H]-	157.563	30932474
DeepCCS	[M-2H]-	191.83	30932474
DeepCCS	[M+Na]+	167.126	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 10V, Positive-QTOF	splash10-001i-0390000000-52f39b3b546c3ae4bd08	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 20V, Positive-QTOF	splash10-053r-0930000000-db7c652dec6b8a113ce8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 40V, Positive-QTOF	splash10-0zgi-9610000000-4ee207e1d9abd929f98c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 10V, Negative-QTOF	splash10-004i-0290000000-ce52077fb1df2eb80832	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 20V, Negative-QTOF	splash10-004r-0790000000-be4c79bac3c328450193	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 40V, Negative-QTOF	splash10-1000-8900000000-85d7d83461abe2e9e2e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 10V, Positive-QTOF	splash10-001i-0090000000-b8f7b2ad54b12c0158e3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 20V, Positive-QTOF	splash10-001i-0390000000-13e3c3e2849e37ed95f6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 40V, Positive-QTOF	splash10-0pc0-1930000000-bfe3326d3296ee0735ed	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 10V, Negative-QTOF	splash10-004i-0090000000-fb2ff0c6ce4213f1f376	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 20V, Negative-QTOF	splash10-004i-2590000000-e71ac4209ccc7a378742	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eremanthin 40V, Negative-QTOF	splash10-004i-1950000000-835bdb7f1dc6210778f0	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

100572

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1534781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Eremanthin (HMDB0302703)

MOL for HMDB0302703 (Eremanthin)

3D MOL for HMDB0302703 (Eremanthin)

3D SDF for HMDB0302703 (Eremanthin)

3D-SDF for HMDB0302703 (Eremanthin)

PDB for HMDB0302703 (Eremanthin)

3D PDB for HMDB0302703 (Eremanthin)

SMILES for HMDB0302703 (Eremanthin)

INCHI for HMDB0302703 (Eremanthin)

Structure for HMDB0302703 (Eremanthin)

3D Structure for HMDB0302703 (Eremanthin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra