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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:56:45 UTC

Update Date

2021-09-23 19:56:45 UTC

HMDB ID

HMDB0302706

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Reynosin

Description

Reynosin 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. Reynosin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Reynosin can be found in sweet bay, which makes reynosin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302706
     RDKit          3D
Reynosin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3296   -0.2678   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    0.3795   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751    1.8358   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786    2.7234   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    2.0383   -0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.8442    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581   -0.1612   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -1.5523   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -1.8458   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -0.8192    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.8880    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575   -1.0732    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -0.9324    1.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1310   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555    1.2624   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5567    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363    2.6398    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654    0.5677   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3061   -1.3469   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598    0.2297   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.6508    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -0.0280   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7152    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -2.2363   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.7963   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.8284   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    0.0976    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575   -1.4659    1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.4221    2.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -2.1411   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -1.4803    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -0.4188   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812   -0.1986   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.9686   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    1.2592    0.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.3162    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555    2.9196    1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.4592   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 02241221422D          

 18 20  0  0  0  0            999 V2000
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302706

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(OC(=O)C3=C)C1C(=C)CCC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-13,16H,1-2,4-7H2,3H3

> <INCHI_KEY>
FKBUODICGDOIGB-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.25512501280471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.205117985

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.677967584774194

> <JCHEM_PKA_STRONGEST_BASIC>
-2.939656978419767

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.6359

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-5a-methyl-3,9-dimethylidene-octahydronaphtho[1,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302706
     RDKit          3D
Reynosin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3296   -0.2678   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    0.3795   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751    1.8358   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786    2.7234   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    2.0383   -0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.8442    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581   -0.1612   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -1.5523   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -1.8458   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -0.8192    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.8880    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575   -1.0732    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -0.9324    1.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1310   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555    1.2624   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5567    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363    2.6398    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654    0.5677   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3061   -1.3469   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598    0.2297   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.6508    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -0.0280   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7152    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -2.2363   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.7963   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.8284   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    0.0976    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575   -1.4659    1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.4221    2.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -2.1411   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -1.4803    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -0.4188   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812   -0.1986   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.9686   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    1.2592    0.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.3162    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555    2.9196    1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.4592   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.417   3.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.790  -1.944   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.895   2.610   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0302706
HETATM    1  C1  UNL     1       4.330  -0.268  -0.340  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.196   0.380  -0.512  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.975   1.836  -0.504  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.879   2.723  -0.601  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.585   2.038  -0.372  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.029   0.844   0.068  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.858  -0.161  -0.755  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.615  -1.552  -0.341  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.138  -1.846  -0.454  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.716  -0.819   0.250  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.442  -0.888   1.740  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.158  -1.073   0.013  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.872  -0.932   1.215  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.788  -0.131  -0.977  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.756   1.262  -0.372  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.369   1.557   0.096  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.136   2.640   0.807  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.365   0.568  -0.299  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.306  -1.347  -0.377  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.260   0.230  -0.167  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.290   0.651   1.124  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.624  -0.028  -1.828  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.003  -1.715   0.682  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.140  -2.236  -1.007  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.120  -1.796  -1.541  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.108  -2.828  -0.023  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.361   0.098   2.203  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.457  -1.466   1.990  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.294  -1.422   2.256  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.276  -2.141  -0.288  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.688  -1.480   1.222  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.857  -0.419  -1.089  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.281  -0.199  -1.940  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.094   1.969  -1.154  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.484   1.259   0.462  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.941   3.316   1.053  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.155   2.920   1.182  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.421   0.459  -1.423  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   12   18
CONECT   11   27   28   29
CONECT   12   13   14   30
CONECT   13   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   17   18
CONECT   17   36   37
CONECT   18   38
END

HMDB0302706
     RDKit          3D
Reynosin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.3296   -0.2678   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    0.3795   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751    1.8358   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786    2.7234   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    2.0383   -0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.8442    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581   -0.1612   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -1.5523   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -1.8458   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -0.8192    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.8880    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575   -1.0732    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -0.9324    1.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1310   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555    1.2624   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5567    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363    2.6398    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654    0.5677   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3061   -1.3469   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598    0.2297   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.6508    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -0.0280   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7152    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -2.2363   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.7963   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.8284   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    0.0976    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575   -1.4659    1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.4221    2.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -2.1411   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -1.4803    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -0.4188   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812   -0.1986   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.9686   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    1.2592    0.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.3162    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555    2.9196    1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.4592   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

6-hydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

Traditional Name

6-hydroxy-5a-methyl-3,9-dimethylidene-octahydronaphtho[1,2-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(OC(=O)C3=C)C1C(=C)CCC2O

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-13,16H,1-2,4-7H2,3H3

InChI Key

FKBUODICGDOIGB-UHFFFAOYSA-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
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

allergen (HMDB: HMDB0302706)

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	1.89	ALOGPS
logP	2.21	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.64 m³·mol⁻¹	ChemAxon
Polarizability	27.26 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]+	159.416	32859911
AllCCS	[M+H-H2O]+	155.712	32859911
AllCCS	[M+Na]+	163.846	32859911
AllCCS	[M+NH4]+	162.856	32859911
AllCCS	[M-H]-	163.482	32859911
AllCCS	[M+Na-2H]-	163.44	32859911
AllCCS	[M+HCOO]-	163.508	32859911
DeepCCS	[M-2H]-	190.416	30932474
DeepCCS	[M+Na]+	165.98	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 10V, Positive-QTOF	splash10-001j-0290000000-ea6114f2f3beebfd3cf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 20V, Positive-QTOF	splash10-0f8a-2940000000-f40674e0e1ee30af18a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 40V, Positive-QTOF	splash10-1003-9310000000-625b3452f1f1eb05d9d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 10V, Negative-QTOF	splash10-0002-0090000000-9f699885deef6bbfb9f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 20V, Negative-QTOF	splash10-0f6t-0190000000-f56459700387deb762b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 40V, Negative-QTOF	splash10-0udi-3920000000-188a644ac0cc6354661e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 10V, Positive-QTOF	splash10-0002-0190000000-873ebc48ff8f48f4d8ab	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 20V, Positive-QTOF	splash10-0002-0690000000-e01590b503a7ea01cb4e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 40V, Positive-QTOF	splash10-052f-2910000000-d0893f983114ddb865f4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 10V, Negative-QTOF	splash10-0002-0090000000-4c1848e20ec9365c5095	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 20V, Negative-QTOF	splash10-0f6t-3190000000-97e1a0b78940e3bf61b7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reynosin 40V, Negative-QTOF	splash10-006y-1930000000-f7f324b2cd354d5afcfc	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

FDB005894

KNApSAcK ID

Not Available

Chemspider ID

89383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98958

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 Reynosin (HMDB0302706)

MOL for HMDB0302706 (Reynosin)

3D MOL for HMDB0302706 (Reynosin)

3D SDF for HMDB0302706 (Reynosin)

3D-SDF for HMDB0302706 (Reynosin)

PDB for HMDB0302706 (Reynosin)

3D PDB for HMDB0302706 (Reynosin)

SMILES for HMDB0302706 (Reynosin)

INCHI for HMDB0302706 (Reynosin)

Structure for HMDB0302706 (Reynosin)

3D Structure for HMDB0302706 (Reynosin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra