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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:23:23 UTC

Update Date

2021-09-23 18:23:23 UTC

HMDB ID

HMDB0302518

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sesquiterpenes

Description

Sesquiterpenes belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Sesquiterpenes is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Sesquiterpenes is a bitter tasting compound found in ceylon cinnamon, pepper (spice), and potato, which makes sesquiterpenes a potential biomarker for the consumption of these food products. Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids .

Structure

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

HMDB0302518
     RDKit          3D
Sesquiterpenes
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.0893    2.3658    1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    1.5271    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    0.3933    0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312   -0.1251    0.8293 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    0.8503    0.9013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    0.1779    0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797    0.4088    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010   -0.8774   -0.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0662   -0.4017   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -1.0735   -0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4676   -0.8288   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.5318   -1.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -0.4557   -0.1084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6696   -1.8521    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186    0.0637   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439    1.1952    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985    1.9877    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    3.1043    1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    3.0282    2.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    3.0053    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    1.7143    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -0.6819    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -1.8214   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955    0.6709   -1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -1.0333   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -0.5301   -1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -2.1326    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234   -1.7491   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987   -0.0110   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    0.4609   -1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -1.2622   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -2.0743    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.5997   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314   -1.9541    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -0.5289   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    1.5712    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 13  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  1
  8 23  1  1
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  1
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv0541 02241220452D          

 18 20  0  0  1  0            999 V2000
    1.5452    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9295   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 13 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 17  1  0  0  0  0
  6 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302518

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1

> <INCHI_KEY>
XJHDMGJURBVLLE-FMBSFYNOSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.97152856346199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.6011767110000004

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.072499727460135

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.8324

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-3H,3aH,4H,5H,9bH-naphtho[1,2-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302518
     RDKit          3D
Sesquiterpenes
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.0893    2.3658    1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    1.5271    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    0.3933    0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312   -0.1251    0.8293 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    0.8503    0.9013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    0.1779    0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797    0.4088    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010   -0.8774   -0.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0662   -0.4017   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -1.0735   -0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4676   -0.8288   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.5318   -1.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -0.4557   -0.1084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6696   -1.8521    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186    0.0637   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439    1.1952    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985    1.9877    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    3.1043    1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    3.0282    2.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    3.0053    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    1.7143    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -0.6819    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -1.8214   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955    0.6709   -1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -1.0333   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -0.5301   -1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -2.1326    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234   -1.7491   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987   -0.0110   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    0.4609   -1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -1.2622   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -2.0743    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.5997   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314   -1.9541    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -0.5289   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    1.5712    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 13  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  1
  8 23  1  1
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  1
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  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       2.884   0.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.060  -0.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.634  -0.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.068  -4.158   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.638  -3.041   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.990  -4.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.362   1.126   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17   11                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0302518
HETATM    1  C1  UNL     1      -0.089   2.366   1.965  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.041   1.527   1.178  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.639   0.393   0.670  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.731  -0.125   0.829  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.740   0.850   0.901  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.928   0.178   0.648  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.080   0.409   1.157  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.601  -0.877  -0.343  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.066  -0.402  -1.686  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.114  -1.074  -0.244  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.468  -0.829  -1.569  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.981  -0.532  -1.522  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.558  -0.456  -0.108  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.670  -1.852   0.480  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.919   0.064  -0.251  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.344   1.195   0.251  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.398   1.988   1.001  1.00  0.00           C  
HETATM   18  O3  UNL     1      -2.773   3.104   1.508  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.691   3.028   2.622  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.540   3.005   1.343  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.487   1.714   2.670  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.754  -0.682   1.807  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.163  -1.821  -0.126  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.896   0.671  -1.823  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.714  -1.033  -2.530  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.189  -0.530  -1.691  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.937  -2.133   0.034  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.623  -1.749  -2.190  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.999  -0.011  -2.124  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.201   0.461  -1.980  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.592  -1.262  -2.119  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.702  -2.074   0.819  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.414  -2.600  -0.299  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.031  -1.954   1.394  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.627  -0.529  -0.811  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.359   1.571   0.137  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4   13
CONECT    4    5   10   22
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   23
CONECT    9   24   25   26
CONECT   10   11   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15
CONECT   14   32   33   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18
END

HMDB0302518
     RDKit          3D
Sesquiterpenes
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.0893    2.3658    1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    1.5271    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    0.3933    0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312   -0.1251    0.8293 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    0.8503    0.9013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    0.1779    0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797    0.4088    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010   -0.8774   -0.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0662   -0.4017   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -1.0735   -0.2440 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4676   -0.8288   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.5318   -1.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -0.4557   -0.1084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6696   -1.8521    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186    0.0637   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439    1.1952    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985    1.9877    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    3.1043    1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    3.0282    2.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    3.0053    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    1.7143    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -0.6819    1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -1.8214   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955    0.6709   -1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -1.0333   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -0.5301   -1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -2.1326    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234   -1.7491   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987   -0.0110   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    0.4609   -1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -1.2622   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -2.0743    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.5997   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314   -1.9541    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -0.5289   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    1.5712    0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 13  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  1
  8 23  1  1
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  1
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

Traditional Name

(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-3H,3aH,4H,5H,9bH-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O

InChI Identifier

InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1

InChI Key

XJHDMGJURBVLLE-FMBSFYNOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0302518)

Food

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)
Ceylon cinnamon (FooDB: FOOD00051)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Fruit

Pome

Asian pear (FooDB: FOOD00291)

Process

Not Available

Role

Not Available

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	1.98	ALOGPS
logP	2.6	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-6.1	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	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	25.97 Å³	ChemAxon
Number of Rings	3	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]+	156.393	32859911
AllCCS	[M+H-H2O]+	152.594	32859911
AllCCS	[M+Na]+	160.939	32859911
AllCCS	[M+NH4]+	159.923	32859911
AllCCS	[M-H]-	163.601	32859911
AllCCS	[M+Na-2H]-	163.481	32859911
AllCCS	[M+HCOO]-	163.463	32859911
DeepCCS	[M+H]+	163.584	30932474
DeepCCS	[M-H]-	161.226	30932474
DeepCCS	[M-2H]-	195.355	30932474
DeepCCS	[M+Na]+	170.582	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.7427 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2498.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	449.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	129.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	590.8 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	753.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1295.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	506.8 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	1530.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	398.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	486.7 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 10V, Positive-QTOF	splash10-0002-0390000000-8de37b3b8a29d7b72190	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 20V, Positive-QTOF	splash10-004j-3940000000-e981fed5f681ed396603	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 40V, Positive-QTOF	splash10-014i-9810000000-e5b6e3c5ca4d9d4f4b83	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 10V, Negative-QTOF	splash10-0002-0090000000-9dd579e1dfab5c39d037	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 20V, Negative-QTOF	splash10-0f6t-0290000000-880f0c0b64e439abf18a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 40V, Negative-QTOF	splash10-0uka-2910000000-587274b8c13b87b9a417	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 10V, Positive-QTOF	splash10-0002-0190000000-197315211c49678ea634	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 20V, Positive-QTOF	splash10-009b-0950000000-4ade3ccd2c47130bce10	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 40V, Positive-QTOF	splash10-00di-1900000000-0b075ffe94c4aac42086	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 10V, Negative-QTOF	splash10-0udj-0090000000-e03d8ebc2740da98e8e0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 20V, Negative-QTOF	splash10-0002-0090000000-430bb7abc185ffccfc2f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquiterpenes 40V, Negative-QTOF	splash10-0006-5980000000-f1bd5b06bcec193da43d	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

FDB004902

KNApSAcK ID

Not Available

Chemspider ID

580838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

667450

PDB ID

Not Available

ChEBI ID

Not Available

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 Sesquiterpenes (HMDB0302518)

MOL for HMDB0302518 (Sesquiterpenes)

3D MOL for HMDB0302518 (Sesquiterpenes)

3D SDF for HMDB0302518 (Sesquiterpenes)

3D-SDF for HMDB0302518 (Sesquiterpenes)

PDB for HMDB0302518 (Sesquiterpenes)

3D PDB for HMDB0302518 (Sesquiterpenes)

SMILES for HMDB0302518 (Sesquiterpenes)

INCHI for HMDB0302518 (Sesquiterpenes)

Structure for HMDB0302518 (Sesquiterpenes)

3D Structure for HMDB0302518 (Sesquiterpenes)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra