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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:49:57 UTC

Update Date

2022-03-07 02:53:58 UTC

HMDB ID

HMDB0034054

Secondary Accession Numbers

HMDB34054

Metabolite Identification

Common Name

Auraptene

Description

Auraptene is found in citrus. Auraptene is isolated from Citrus aurantium (Seville orange) and bael fruit (Aegle marmelos) Auraptene is a natural bioactive monoterpene coumarin ether. It was first isolated from members of the genus Citrus. Auraptene has shown a remarkable effect in the prevention of degenerative diseases. Many studies have reported the effect of auraptene as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models. The effect in humans is not yet known

Structure

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

HMDB0034054
     RDKit          3D
Auraptene
 44 45  0  0  0  0  0  0  0  0999 V2000
   -3.1831   -0.3183   -1.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2693   -0.0934   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.0502   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.9175   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8646   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.9151    1.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    0.6399    1.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -0.5659    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.5638    1.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028   -0.6951    2.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1787    1.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593   -0.6852    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5090    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.9065    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680    0.1735   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9567    0.5751   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781   -0.2089   -2.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9486   -1.3920   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5008   -2.1251   -3.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8273   -1.7611   -1.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -1.0315   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -1.4471   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -1.1572   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885   -0.6328   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    0.6052   -2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9865   -2.0543   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1765   -0.7612   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8418   -1.0783   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0581    1.0486    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.6851   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753    2.8976   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9922    2.2865    2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529    2.7077    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343   -0.8849    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -1.3347    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -0.2908    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.4851    1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080   -1.4832    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -0.6461    3.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.1084    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198    1.8459    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957    1.4965   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5026    0.0437   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.3991   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  1  0
M  END


  Mrv0541 05061307322D          

 22 23  0  0  0  0            999 V2000
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 12 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15 11  2  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  2  0  0  0  0
 19 10  1  0  0  0  0
 20 19  2  0  0  0  0
 21 12  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034054

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

> <INCHI_KEY>
RSDDHGSKLOSQFK-RVDMUPIBSA-N

> <FORMULA>
C19H22O3

> <MOLECULAR_WEIGHT>
298.3762

> <EXACT_MASS>
298.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.4514690605758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
4.646648714333334

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.865488983138084

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
90.93259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
auraptene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034054
     RDKit          3D
Auraptene
 44 45  0  0  0  0  0  0  0  0999 V2000
   -3.1831   -0.3183   -1.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2693   -0.0934   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.0502   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.9175   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8646   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.9151    1.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    0.6399    1.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -0.5659    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.5638    1.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028   -0.6951    2.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1787    1.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593   -0.6852    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5090    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.9065    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680    0.1735   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9567    0.5751   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781   -0.2089   -2.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9486   -1.3920   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5008   -2.1251   -3.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8273   -1.7611   -1.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -1.0315   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -1.4471   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -1.1572   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885   -0.6328   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    0.6052   -2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9865   -2.0543   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1765   -0.7612   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8418   -1.0783   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0581    1.0486    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.6851   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753    2.8976   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9922    2.2865    2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529    2.7077    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343   -0.8849    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -1.3347    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -0.2908    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.4851    1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080   -1.4832    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -0.6461    3.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.1084    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198    1.8459    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957    1.4965   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5026    0.0437   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.3991   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  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      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4   14                                                       
CONECT    6    4   15                                                       
CONECT    7    9   16                                                       
CONECT    8   10   16                                                       
CONECT    9    7   17                                                       
CONECT   10    8   19                                                       
CONECT   11   12   15                                                       
CONECT   12   11   21                                                       
CONECT   13   17   18                                                       
CONECT   14    1    2    5                                                  
CONECT   15    3    6   11                                                  
CONECT   16    7    8   18                                                  
CONECT   17    9   13   21                                                  
CONECT   18   13   16   22                                                  
CONECT   19   10   20   22                                                  
CONECT   20   19                                                            
CONECT   21   12   17                                                       
CONECT   22   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0034054
HETATM    1  C1  UNL     1      -3.183  -0.318  -1.933  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.269  -0.093  -0.951  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.420  -1.050  -0.942  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.240   0.917  -0.098  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.126   1.865  -0.088  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.350   1.915   1.196  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.701   0.640   1.574  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.503  -0.566   1.864  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.366   0.564   1.689  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.303  -0.695   2.062  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.196  -1.179   1.137  1.00  0.00           O  
HETATM   12  C11 UNL     1       2.359  -0.685   0.633  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.913   0.509   1.018  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.105   0.906   0.425  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.768   0.173  -0.526  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.957   0.575  -1.113  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.578  -0.209  -2.068  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.949  -1.392  -2.391  1.00  0.00           C  
HETATM   19  O2  UNL     1       6.501  -2.125  -3.264  1.00  0.00           O  
HETATM   20  O3  UNL     1       4.827  -1.761  -1.831  1.00  0.00           O  
HETATM   21  C18 UNL     1       4.209  -1.031  -0.913  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.033  -1.447  -0.345  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.459  -1.157  -2.585  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.289  -0.633  -1.360  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.989   0.605  -2.523  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.986  -2.054  -0.717  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.177  -0.761  -0.183  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.842  -1.078  -1.967  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.058   1.049   0.596  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.388   1.685  -0.903  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.575   2.898  -0.209  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.992   2.286   2.036  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.553   2.708   1.078  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.234  -0.885   2.922  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.266  -1.335   1.128  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.595  -0.291   1.877  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.177   1.485   1.489  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.508  -1.483   2.167  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.723  -0.646   3.104  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.429   1.108   1.773  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.520   1.846   0.742  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.396   1.497  -0.825  1.00  0.00           H  
HETATM   43  H21 UNL     1       7.503   0.044  -2.564  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.624  -2.399  -0.675  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    4
CONECT    3   26   27   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8    9    9
CONECT    8   34   35   36
CONECT    9   10   37
CONECT   10   11   38   39
CONECT   11   12
CONECT   12   13   13   22
CONECT   13   14   40
CONECT   14   15   15   41
CONECT   15   16   21
CONECT   16   17   17   42
CONECT   17   18   43
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   22
CONECT   22   44
END

HMDB0034054
     RDKit          3D
Auraptene
 44 45  0  0  0  0  0  0  0  0999 V2000
   -3.1831   -0.3183   -1.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2693   -0.0934   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.0502   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.9175   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260    1.8646   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.9151    1.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    0.6399    1.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -0.5659    1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.5638    1.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028   -0.6951    2.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1787    1.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593   -0.6852    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5090    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.9065    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680    0.1735   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9567    0.5751   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781   -0.2089   -2.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9486   -1.3920   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5008   -2.1251   -3.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8273   -1.7611   -1.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -1.0315   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -1.4471   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -1.1572   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885   -0.6328   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    0.6052   -2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9865   -2.0543   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1765   -0.7612   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8418   -1.0783   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0581    1.0486    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.6851   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753    2.8976   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9922    2.2865    2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529    2.7077    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343   -0.8849    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -1.3347    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -0.2908    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    1.4851    1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080   -1.4832    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -0.6461    3.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.1084    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198    1.8459    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957    1.4965   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5026    0.0437   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.3991   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one	ChEBI
7-Geranyloxycoumarin	ChEBI
7-O-Geranylumbelliferone	ChEBI
7-(3,7-Dimethyl-2,6-octadienyl)oxy-2H-1-benzopyran-2-one, 9ci	HMDB
7-([(2E)-3,7-Dimethyl-2,6-octadienyl]oxy)-2H-chromen-2-one	HMDB
7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-(e)-coumarin	HMDB
Aurapten	HMDB
Feronialactone	HMDB
O-Geranylumbelliferone	HMDB
7-(Geranyloxy)coumarin	MeSH

Chemical Formula

C₁₉H₂₂O₃

Average Molecular Weight

298.3762

Monoisotopic Molecular Weight

298.15689457

IUPAC Name

7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one

Traditional Name

auraptene

CAS Registry Number

495-02-3

SMILES

CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

InChI Key

RSDDHGSKLOSQFK-RVDMUPIBSA-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
Coumarin
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034054)

Source

Endogenous

Endogenous (HMDB: HMDB0034054)

Plant

Plant (HMDB: HMDB0034054)

Animal

Animal (HMDB: HMDB0034054)

Exogenous

Food

Food (HMDB: HMDB0034054)

Fruit

Citrus

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0034054)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034054)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034054)

Lipid metabolism pathway (HMDB: HMDB0034054)

Cellular process

Cell signaling (HMDB: HMDB0034054)

Biochemical process

Lipid transport (HMDB: HMDB0034054)

Role

Biological role

Energy source (HMDB: HMDB0034054)
Anti aggregant (HMDB: HMDB0034054)
Anti peroxidant (HMDB: HMDB0034054)
Anti spasmodic (HMDB: HMDB0034054)
Anti superoxidogenic (HMDB: HMDB0034054)
Quinone-reductase inducer (HMDB: HMDB0034054)

Modulator

Inhibitor

Chemopreventive inhibitor (HMDB: HMDB0034054)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0034054)
Anticancer agent (HMDB: HMDB0034054)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68 °C	Not Available
Boiling Point	455.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.17 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.690 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	158.294	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001254

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	5.85	ALOGPS
logP	4.65	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.93 m³·mol⁻¹	ChemAxon
Polarizability	34.45 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]+	174.08	31661259
DarkChem	[M-H]-	173.702	31661259
DeepCCS	[M+H]+	177.446	30932474
DeepCCS	[M-H]-	175.088	30932474
DeepCCS	[M-2H]-	208.216	30932474
DeepCCS	[M+Na]+	183.934	30932474
AllCCS	[M+H]+	172.3	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	177.6	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	176.7	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.	10.0 minutes	32390414
Predicted by Siyang on May 30, 2022	18.8622 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2706.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	561.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	240.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	295.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	708.7 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	701.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1592.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	608.3 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	1404.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	378.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	549.3 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Auraptene	CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1	3361.4	Standard polar	33892256
Auraptene	CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1	2501.8	Standard non polar	33892256
Auraptene	CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1	2628.6	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 - Auraptene GC-MS (Non-derivatized) - 70eV, Positive	splash10-02u0-8890000000-e171be9caec4d2a11ee5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Auraptene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Auraptene LC-ESI-qTof , Positive-QTOF	splash10-0040-0951000000-79a592191716b8a00de8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Auraptene , positive-QTOF	splash10-03di-0900000000-29a7bac9e8f94ca0d09c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Auraptene , positive-QTOF	splash10-08fr-1900000000-b149439e3218a537d0ac	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 10V, Positive-QTOF	splash10-0002-0490000000-32af6826fbefdf3a35ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 20V, Positive-QTOF	splash10-07br-5960000000-d750ef85cd2d4a24a646	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 40V, Positive-QTOF	splash10-0gb9-9500000000-d8284943e9e7d046ea7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 10V, Negative-QTOF	splash10-0002-0390000000-50c66a59f956b01fdb9a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 20V, Negative-QTOF	splash10-03di-0930000000-1a7ac827ff79742e805c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 40V, Negative-QTOF	splash10-014i-1900000000-7a051e8b339080b6467d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 10V, Negative-QTOF	splash10-03dj-1940000000-dc613a802ac097906469	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 20V, Negative-QTOF	splash10-03di-0900000000-ebcff9e2f7b33fef0429	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 40V, Negative-QTOF	splash10-0159-0900000000-833c0e8e483ddb0387a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 10V, Positive-QTOF	splash10-03dj-0970000000-509fac58feb4fa761513	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 20V, Positive-QTOF	splash10-03ea-9500000000-190906af7b5b2a65c2f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auraptene 40V, Positive-QTOF	splash10-0929-9700000000-4aeadfc84ff6db8dd015	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB012300

KNApSAcK ID

C00029763

Chemspider ID

1267148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Auraptene

METLIN ID

Not Available

PubChem Compound

1550607

PDB ID

Not Available

ChEBI ID

134355

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1011441

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

de Medina P, Genovese S, Paillasse MR, Mazaheri M, Caze-Subra S, Bystricky K, Curini M, Silvente-Poirot S, Epifano F, Poirot M: Auraptene is an inhibitor of cholesterol esterification and a modulator of estrogen receptors. Mol Pharmacol. 2010 Nov;78(5):827-36. doi: 10.1124/mol.110.065250. Epub 2010 Aug 11. [PubMed:20702762 ]
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 Auraptene (HMDB0034054)

MOL for HMDB0034054 (Auraptene)

3D MOL for HMDB0034054 (Auraptene)

3D SDF for HMDB0034054 (Auraptene)

3D-SDF for HMDB0034054 (Auraptene)

PDB for HMDB0034054 (Auraptene)

3D PDB for HMDB0034054 (Auraptene)

SMILES for HMDB0034054 (Auraptene)

INCHI for HMDB0034054 (Auraptene)

Structure for HMDB0034054 (Auraptene)

3D Structure for HMDB0034054 (Auraptene)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra