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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:13:12 UTC

Update Date

2021-09-23 20:13:12 UTC

HMDB ID

HMDB0302733

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Anthecotulide

Description

Anthecotulide is a member of the class of compounds known as terpene lactones. Terpene lactones are prenol lipids containing a lactone ring. Anthecotulide is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Anthecotulide can be found in german camomile, which makes anthecotulide a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302733
     RDKit          3D
Anthecotulide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.8486    1.1683    1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    0.8056    0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    1.6922   -0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7187    2.9572   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    0.9246   -1.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -0.4103   -1.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334   -0.5604    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.9471    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.0338    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573   -0.4949   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325   -1.9377   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    0.4184   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    0.0252   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.9899    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    0.7796   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869    0.4474    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.7170    1.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6861    1.2738   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1154    2.1887    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1613    0.4201    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6337   -0.5379   -1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.1668   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -1.2477    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -1.9990    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -0.8972    1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879    1.0152    0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -2.5696    0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8795   -2.1656   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -2.2080   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    0.3866   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069    1.4739   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.6497   -0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6080   -0.8352    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -0.5672    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114   -1.6736    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5931    0.6124    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126    1.6021   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7471    2.1181    0.7080 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  2  0
 13 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
  7  2  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 02241212592D          

 18 18  0  0  0  0            999 V2000
   -1.1491   -0.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8165    0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616    1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4817    0.2546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    1.7066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465    1.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2455    0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6744    0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3889   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1034    0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3889   -0.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599   -0.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178   -0.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5323    0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178   -0.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302733

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CC(=O)C\C(C)=C\CC1COC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-10(2)7-14(16)8-11(3)5-6-13-9-18-15(17)12(13)4/h5,7,13H,4,6,8-9H2,1-3H3/b11-5+

> <INCHI_KEY>
WSKLYRKBPFVGEJ-VZUCSPMQSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.192492904844503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-3-methylideneoxolan-2-one

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.2545524206666667

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.943029055772236

> <JCHEM_PKA_STRONGEST_BASIC>
-4.451724076527883

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
72.7799

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-3-methylideneoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302733
     RDKit          3D
Anthecotulide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.8486    1.1683    1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    0.8056    0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    1.6922   -0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7187    2.9572   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    0.9246   -1.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -0.4103   -1.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334   -0.5604    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.9471    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.0338    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573   -0.4949   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325   -1.9377   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    0.4184   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    0.0252   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.9899    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    0.7796   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869    0.4474    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.7170    1.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6861    1.2738   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1154    2.1887    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1613    0.4201    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6337   -0.5379   -1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.1668   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -1.2477    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -1.9990    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -0.8972    1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879    1.0152    0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -2.5696    0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8795   -2.1656   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -2.2080   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    0.3866   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069    1.4739   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.6497   -0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6080   -0.8352    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -0.5672    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114   -1.6736    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5931    0.6124    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126    1.6021   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7471    2.1181    0.7080 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  2  0
 13 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
  7  2  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.145  -0.430   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.391   0.475   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.915   1.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.375   1.940   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.899   0.475   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.470   3.186   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.820   3.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.725  -0.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.058   0.475   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.392  -0.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.726   0.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.059  -0.295   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.393   0.475   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -10.059  -1.835   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -7.392  -1.835   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.727  -0.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.060   0.475   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.727  -1.835   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    1    4                                                       
CONECT    6    4                                                            
CONECT    7    3                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   16                                                       
CONECT   14   12                                                            
CONECT   15   10                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0302733
HETATM    1  C1  UNL     1      -4.849   1.168   1.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.162   0.806   0.404  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.672   1.692  -0.645  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.719   2.957  -0.596  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.148   0.925  -1.704  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.608  -0.410  -1.490  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.733  -0.560   0.007  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.423  -0.947   0.653  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.324  -0.034   0.286  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.257  -0.495  -0.324  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.133  -1.938  -0.657  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.859   0.418  -0.700  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.140   0.025  -0.050  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.101  -0.990   0.701  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.348   0.780  -0.281  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.487   0.447   0.284  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.560  -0.717   1.177  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.686   1.274  -0.004  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.115   2.189   1.691  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.161   0.420   2.199  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.634  -0.538  -1.946  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.961  -1.167  -1.935  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.540  -1.248   0.301  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.213  -1.999   0.382  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.539  -0.897   1.752  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.388   1.015   0.514  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.261  -2.570   0.251  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.879  -2.166  -1.039  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.858  -2.208  -1.449  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.972   0.387  -1.800  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.607   1.474  -0.444  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.274   1.650  -0.954  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.608  -0.835   1.543  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.910  -0.567   2.082  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.311  -1.674   0.697  1.00  0.00           H  
HETATM   36  H18 UNL     1       6.593   0.612   0.047  1.00  0.00           H  
HETATM   37  H19 UNL     1       5.613   1.602  -1.056  1.00  0.00           H  
HETATM   38  H20 UNL     1       5.747   2.118   0.708  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   21   22
CONECT    7    8   23
CONECT    8    9   24   25
CONECT    9   10   10   26
CONECT   10   11   12
CONECT   11   27   28   29
CONECT   12   13   30   31
CONECT   13   14   14   15
CONECT   15   16   16   32
CONECT   16   17   18
CONECT   17   33   34   35
CONECT   18   36   37   38
END

HMDB0302733
     RDKit          3D
Anthecotulide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.8486    1.1683    1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    0.8056    0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    1.6922   -0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7187    2.9572   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    0.9246   -1.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -0.4103   -1.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334   -0.5604    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.9471    0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.0338    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573   -0.4949   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325   -1.9377   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    0.4184   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    0.0252   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.9899    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    0.7796   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869    0.4474    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.7170    1.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6861    1.2738   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1154    2.1887    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1613    0.4201    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6337   -0.5379   -1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.1668   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -1.2477    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -1.9990    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -0.8972    1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879    1.0152    0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -2.5696    0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8795   -2.1656   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -2.2080   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    0.3866   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069    1.4739   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.6497   -0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6080   -0.8352    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099   -0.5672    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114   -1.6736    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5931    0.6124    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126    1.6021   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7471    2.1181    0.7080 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  2  0
 13 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
  7  2  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-3-methylideneoxolan-2-one

Traditional Name

4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-3-methylideneoxolan-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)C\C(C)=C\CC1COC(=O)C1=C

InChI Identifier

InChI=1S/C15H20O3/c1-10(2)7-14(16)8-11(3)5-6-13-9-18-15(17)12(13)4/h5,7,13H,4,6,8-9H2,1-3H3/b11-5+

InChI Key

WSKLYRKBPFVGEJ-VZUCSPMQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Monocyclic monoterpenoid
Monoterpenoid
Gamma butyrolactone
Acryloyl-group
Enone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Alpha,beta-unsaturated ketone
Lactone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

German camomile (FooDB: FOOD00107)

Process

Not Available

Role

Biological role

allergen (HMDB: HMDB0302733)

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	3.13	ALOGPS
logP	3.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	16.94	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.78 m³·mol⁻¹	ChemAxon
Polarizability	27.19 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
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.257	32859911
AllCCS	[M+Na]+	163.258	32859911
AllCCS	[M+NH4]+	162.284	32859911
AllCCS	[M-H]-	163.197	32859911
AllCCS	[M+Na-2H]-	163.685	32859911
AllCCS	[M+HCOO]-	164.344	32859911
DeepCCS	[M+H]+	163.322	30932474
DeepCCS	[M-H]-	160.964	30932474
DeepCCS	[M-2H]-	193.851	30932474
DeepCCS	[M+Na]+	169.416	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anthecotulide,1TMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	2184.3	Semi standard non polar	33892256
Anthecotulide,1TMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	1988.8	Standard non polar	33892256
Anthecotulide,1TMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	2475.2	Standard polar	33892256
Anthecotulide,1TBDMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	2393.4	Semi standard non polar	33892256
Anthecotulide,1TBDMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	2226.8	Standard non polar	33892256
Anthecotulide,1TBDMS,isomer #1	C=C1C(=O)OCC1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	2580.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 10V, Positive-QTOF	splash10-0002-1490000000-3e8d58c3e32360873aa3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 20V, Positive-QTOF	splash10-01q9-7930000000-89ddb9dfe48338c797a1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 40V, Positive-QTOF	splash10-0pc3-9200000000-0306c05849d6ee951e98	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 10V, Negative-QTOF	splash10-0002-1090000000-c904f8ecf0073b1e6faf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 20V, Negative-QTOF	splash10-0k92-6390000000-c5d5becb00fbc5a35371	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 40V, Negative-QTOF	splash10-0a4i-9210000000-d8771c1a206308754339	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 10V, Positive-QTOF	splash10-001j-6930000000-0f25b6b633ee6c3af191	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 20V, Positive-QTOF	splash10-00pi-9510000000-dce3b1f4c42edef4d4c7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 40V, Positive-QTOF	splash10-069u-9800000000-601a014efd69160f6e73	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 10V, Negative-QTOF	splash10-0002-0190000000-7dd22748af2682aa6178	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 20V, Negative-QTOF	splash10-002b-2970000000-cb3a3329ee9250aeecd2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anthecotulide 40V, Negative-QTOF	splash10-01c0-9400000000-5132916e765ab7994f29	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

FDB005982

KNApSAcK ID

C00033644

Chemspider ID

10136417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11962174

PDB ID

Not Available

ChEBI ID

141397

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

Not Available

Showing metabocard for Anthecotulide (HMDB0302733)

MOL for HMDB0302733 (Anthecotulide)

3D MOL for HMDB0302733 (Anthecotulide)

3D SDF for HMDB0302733 (Anthecotulide)

3D-SDF for HMDB0302733 (Anthecotulide)

PDB for HMDB0302733 (Anthecotulide)

3D PDB for HMDB0302733 (Anthecotulide)

SMILES for HMDB0302733 (Anthecotulide)

INCHI for HMDB0302733 (Anthecotulide)

Structure for HMDB0302733 (Anthecotulide)

3D Structure for HMDB0302733 (Anthecotulide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra