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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:25 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030854

Secondary Accession Numbers

HMDB30854

Metabolite Identification

Common Name

(S)-Auraptenol

Description

(S)-Auraptenol belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one) (S)-Auraptenol has been detected, but not quantified in, sweet oranges (Citrus sinensis). This could make (S)-auraptenol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (S)-Auraptenol.

Structure

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

HMDB0030854
     RDKit          3D
(S)-Auraptenol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2299    0.5586   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    0.3643   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2611    0.4012    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030    0.1149    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -1.0938    0.8884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    0.1543   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.0965   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -1.3788    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -2.4580   -0.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747   -3.7854    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451   -1.5587    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771   -0.4773    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.7965    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    1.9029    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    3.1383    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.2920   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980    4.4493   -0.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    2.2245   -0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297    1.0229   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2037    0.7340   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.5302   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.4520    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2921    1.3808    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670    0.2694   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318    0.9075    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -1.5822    0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773    1.1329   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641   -0.6427   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -4.3783    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076   -4.2201   -0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207   -3.8456    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716   -2.5570    0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693   -0.5847    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5431    1.7410    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    3.9958    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  7  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END


  Mrv0541 05061305332D          

 19 20  0  0  0  0            999 V2000
    0.0000    4.9500    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
   -1.4289    3.3000    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  2  0  0  0  0
 18  3  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030854

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-9(2)12(16)8-11-13(18-3)6-4-10-5-7-14(17)19-15(10)11/h4-7,12,16H,1,8H2,2-3H3

> <INCHI_KEY>
SQSRYWNOKPJENY-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.17464535235587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.1813779523333325

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.395662465776617

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0631372374693084

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
72.69760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030854
     RDKit          3D
(S)-Auraptenol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2299    0.5586   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    0.3643   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2611    0.4012    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030    0.1149    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -1.0938    0.8884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    0.1543   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.0965   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -1.3788    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -2.4580   -0.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747   -3.7854    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451   -1.5587    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771   -0.4773    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.7965    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    1.9029    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    3.1383    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.2920   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980    4.4493   -0.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    2.2245   -0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297    1.0229   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2037    0.7340   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.5302   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.4520    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2921    1.3808    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670    0.2694   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318    0.9075    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -1.5822    0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773    1.1329   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641   -0.6427   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -4.3783    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076   -4.2201   -0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207   -3.8456    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716   -2.5570    0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693   -0.5847    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5431    1.7410    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    3.9958    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  7  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  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       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   18                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   13                                                       
CONECT    7    5   14                                                       
CONECT    8   11   12                                                       
CONECT    9    1    2   12                                                  
CONECT   10    4    5   15                                                  
CONECT   11    8   13   15                                                  
CONECT   12    8    9   16                                                  
CONECT   13    6   11   18                                                  
CONECT   14    7   17   19                                                  
CONECT   15   10   11   19                                                  
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18    3   13                                                       
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0030854
HETATM    1  C1  UNL     1      -3.230   0.559  -1.700  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.041   0.364  -0.406  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.261   0.401   0.480  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.703   0.115   0.188  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.715  -1.094   0.888  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.631   0.154  -0.876  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.714  -0.097  -0.296  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.077  -1.379   0.017  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.233  -2.458  -0.200  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.575  -3.785   0.109  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.345  -1.559   0.569  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.177  -0.477   0.780  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.773   0.797   0.450  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.566   1.903   0.643  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.089   3.138   0.288  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.836   3.292  -0.254  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.398   4.449  -0.582  1.00  0.00           O  
HETATM   18  O4  UNL     1       1.104   2.224  -0.425  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.530   1.023  -0.096  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.204   0.734  -2.095  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.343   0.530  -2.349  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.242  -0.452   1.192  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.292   1.381   1.036  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.167   0.269  -0.144  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.432   0.908   0.936  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.579  -1.582   0.779  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.677   1.133  -1.386  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.864  -0.643  -1.610  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.364  -4.378   0.109  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.208  -4.220  -0.694  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.021  -3.846   1.100  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.672  -2.557   0.831  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.169  -0.585   1.207  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.543   1.741   1.071  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.717   3.996   0.442  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    4
CONECT    3   22   23   24
CONECT    4    5    6   25
CONECT    5   26
CONECT    6    7   27   28
CONECT    7    8    8   19
CONECT    8    9   11
CONECT    9   10
CONECT   10   29   30   31
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   19   19
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   18
CONECT   18   19
END

HMDB0030854
     RDKit          3D
(S)-Auraptenol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2299    0.5586   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    0.3643   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2611    0.4012    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030    0.1149    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -1.0938    0.8884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    0.1543   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.0965   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -1.3788    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -2.4580   -0.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747   -3.7854    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451   -1.5587    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771   -0.4773    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.7965    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    1.9029    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    3.1383    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.2920   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980    4.4493   -0.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    2.2245   -0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297    1.0229   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2037    0.7340   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.5302   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.4520    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2921    1.3808    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670    0.2694   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318    0.9075    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -1.5822    0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773    1.1329   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641   -0.6427   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -4.3783    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076   -4.2201   -0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207   -3.8456    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716   -2.5570    0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693   -0.5847    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5431    1.7410    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    3.9958    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  7  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Auraptenol	MeSH

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxy-2H-chromen-2-one

Traditional Name

8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxychromen-2-one

CAS Registry Number

1221-43-8

SMILES

COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C15H16O4/c1-9(2)12(16)8-11-13(18-3)6-4-10-5-7-14(17)19-15(10)11/h4-7,12,16H,1,8H2,2-3H3

InChI Key

SQSRYWNOKPJENY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Secondary alcohol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	109 - 110 °C	Not Available
Boiling Point	446.73 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	504.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.235 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.18	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.7 m³·mol⁻¹	ChemAxon
Polarizability	27.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.437	31661259
DarkChem	[M-H]-	159.347	31661259
DeepCCS	[M+H]+	166.815	30932474
DeepCCS	[M-H]-	164.458	30932474
DeepCCS	[M-2H]-	197.344	30932474
DeepCCS	[M+Na]+	172.909	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	161.9	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.	6.7 minutes	32390414
Predicted by Siyang on May 30, 2022	12.642 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1836.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	355.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	450.2 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	507.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	998.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	422.8 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	1347.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	366.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Auraptenol	COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1	3095.7	Standard polar	33892256
(S)-Auraptenol	COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1	2236.5	Standard non polar	33892256
(S)-Auraptenol	COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1	2293.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Auraptenol,1TMS,isomer #1	C=C(C)C(CC1=C(OC)C=CC2=C1OC(=O)C=C2)O[Si](C)(C)C	2262.8	Semi standard non polar	33892256
(S)-Auraptenol,1TBDMS,isomer #1	C=C(C)C(CC1=C(OC)C=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C	2516.5	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 - (S)-Auraptenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9660000000-a4f2c9023842a06d8dcf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Auraptenol GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9551000000-3e86f74ff09eeffab549	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Auraptenol 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 - (S)-Auraptenol , positive-QTOF	splash10-001r-0910000000-662f2f1cc2095028273d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Auraptenol , positive-QTOF	splash10-0019-0910000000-5e7039d4fb161baaee2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Auraptenol , positive-QTOF	splash10-001c-0930000000-bdb207ffa052782e4c65	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Positive-QTOF	splash10-01ox-0090000000-8d516cd89de3a5c0e889	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Positive-QTOF	splash10-006x-9150000000-69694ef12c68a4981318	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Positive-QTOF	splash10-00dl-9560000000-880f9122e164f9ba9611	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Negative-QTOF	splash10-0a4i-0190000000-a426b019748239d6aa20	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Negative-QTOF	splash10-056r-0790000000-2bfa6c766af259da968c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Negative-QTOF	splash10-00sj-8930000000-233d1073f800d653738e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Negative-QTOF	splash10-0a4i-0190000000-0d14923dded6ed40c76c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Negative-QTOF	splash10-0929-4490000000-9ced2045f6dd65e0e816	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Negative-QTOF	splash10-0092-3920000000-352c40feab0b1b5048e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Positive-QTOF	splash10-01ox-0690000000-271563afd7d1c20a5f36	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Positive-QTOF	splash10-002u-6960000000-ee76e2f7ba222983847a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Positive-QTOF	splash10-099d-2900000000-479897eca0c873b501e6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002813

KNApSAcK ID

Not Available

Chemspider ID

10235598

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13343540

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637261

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

(S)-Auraptenol → {[1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methylbut-3-en-2-yl]oxy}sulfonic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

(S)-Auraptenol → 3,4,5-trihydroxy-6-{[1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methylbut-3-en-2-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for (S)-Auraptenol (HMDB0030854)

MOL for HMDB0030854 ((S)-Auraptenol)

3D MOL for HMDB0030854 ((S)-Auraptenol)

3D SDF for HMDB0030854 ((S)-Auraptenol)

3D-SDF for HMDB0030854 ((S)-Auraptenol)

PDB for HMDB0030854 ((S)-Auraptenol)

3D PDB for HMDB0030854 ((S)-Auraptenol)

SMILES for HMDB0030854 ((S)-Auraptenol)

INCHI for HMDB0030854 ((S)-Auraptenol)

Structure for HMDB0030854 ((S)-Auraptenol)

3D Structure for HMDB0030854 ((S)-Auraptenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions