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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:57:53 UTC

Update Date

2021-09-23 19:57:54 UTC

HMDB ID

HMDB0302708

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Rothin B

Description

Rothin b 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. Rothin b is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Rothin b can be found in sweet bay, which makes rothin b a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302708
     RDKit          3D
Rothin B
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.1917   -0.8136   -0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.9669    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242   -2.2411    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.3147    0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083   -2.0270    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -0.9538    0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.0064    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489    0.9642   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    1.8680   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    1.7341   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.0074    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.9370    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    0.8866   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100    0.4656   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301   -0.8111    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -1.2980    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.5094   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.3600    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2339    2.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936   -1.6148   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659    0.1668   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.2804   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    0.4789    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511    0.3924   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    2.3029   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    2.5101    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    2.3498   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    2.3354    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.4360    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    2.8160    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018    0.1018   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796    1.8202   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7543    0.2782   -1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952    1.2798    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3293   -0.6692    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -1.5568   -0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196   -2.9359   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598   -3.1107   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046   -0.4278    2.4846 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END

  Mrv0541 02241223402D          

 19 21  0  0  0  0            999 V2000
   -1.9430    0.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717   -0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -1.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0808   -1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283   -2.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3766   -1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -0.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5668    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5668    0.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430    0.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857   -0.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6479    0.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430    1.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857    2.2671    0.0000 O   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
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302708

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(=C)C1(O)C1OC(=O)C(=C)C1C(O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-5-4-6-14(3)7-10(16)11-9(2)13(17)19-12(11)15(8,14)18/h10-12,16,18H,1-2,4-7H2,3H3

> <INCHI_KEY>
CMVJNYSIDKGGLC-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.92395249008817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.3212361369999999

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.847297867027688

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.302999093508956

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9066168675496264

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
68.83419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-hexahydro-3aH-naphtho[1,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302708
     RDKit          3D
Rothin B
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.1917   -0.8136   -0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.9669    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242   -2.2411    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.3147    0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083   -2.0270    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -0.9538    0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.0064    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489    0.9642   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    1.8680   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    1.7341   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.0074    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.9370    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    0.8866   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100    0.4656   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301   -0.8111    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -1.2980    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.5094   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.3600    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2339    2.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936   -1.6148   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659    0.1668   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.2804   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    0.4789    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511    0.3924   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    2.3029   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    2.5101    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    2.3498   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    2.3354    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.4360    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    2.8160    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018    0.1018   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796    1.8202   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7543    0.2782   -1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952    1.2798    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3293   -0.6692    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -1.5568   -0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196   -2.9359   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598   -3.1107   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046   -0.4278    2.4846 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  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  O   UNK     0      -3.627   0.453   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.115   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.814  -1.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.301  -2.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.511  -3.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.151  -3.628   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.359  -4.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.570  -3.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.267  -1.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.627  -1.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.267   3.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.058   2.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.058   0.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.454   0.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.907  -1.057   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.965  -0.151   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.209   1.663   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.454   2.872   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.907   4.232   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   15                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13   18                                                  
CONECT   13    2   12   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15    4    9   14   16                                             
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   12   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0302708
HETATM    1  C1  UNL     1       4.192  -0.814  -0.499  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.016  -0.967   0.079  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.524  -2.241   0.593  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.183  -3.315   0.601  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.208  -2.027   1.061  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.728  -0.954   0.295  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.928  -0.006   0.367  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.649   0.964  -0.759  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.704   1.868  -0.893  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.433   1.734  -0.365  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.733   1.007   0.144  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.415   1.937   1.171  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.759   0.887  -0.980  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.110   0.466  -0.445  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.030  -0.811   0.353  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.643  -1.298   0.252  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.413  -2.509  -0.221  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.548  -0.360   0.703  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.604  -0.234   2.109  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.894  -1.615  -0.644  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.466   0.167  -0.846  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.686  -1.280  -0.777  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.015   0.479   1.340  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.551   0.392  -1.682  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.943   2.303  -0.053  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.782   2.510   0.379  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.133   2.350  -1.253  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.615   2.335   1.839  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.222   1.436   1.706  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.859   2.816   0.658  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.402   0.102  -1.678  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.880   1.820  -1.542  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.754   0.278  -1.328  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.595   1.280   0.131  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.329  -0.669   1.424  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.749  -1.557  -0.045  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.420  -2.936  -0.325  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.260  -3.111  -0.521  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.305  -0.428   2.485  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   22
CONECT    7    8   23
CONECT    8    9   10   24
CONECT    9   25
CONECT   10   11   26   27
CONECT   11   12   13   18
CONECT   12   28   29   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   17   18
CONECT   17   37   38
CONECT   18   19
CONECT   19   39
END

HMDB0302708
     RDKit          3D
Rothin B
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.1917   -0.8136   -0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.9669    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242   -2.2411    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.3147    0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083   -2.0270    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -0.9538    0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.0064    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489    0.9642   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    1.8680   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    1.7341   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.0074    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.9370    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    0.8866   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100    0.4656   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301   -0.8111    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -1.2980    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.5094   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.3600    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2339    2.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936   -1.6148   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659    0.1668   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.2804   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    0.4789    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511    0.3924   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    2.3029   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    2.5101    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    2.3498   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    2.3354    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.4360    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592    2.8160    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018    0.1018   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796    1.8202   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7543    0.2782   -1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952    1.2798    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3293   -0.6692    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -1.5568   -0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196   -2.9359   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598   -3.1107   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046   -0.4278    2.4846 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

Traditional Name

4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-hexahydro-3aH-naphtho[1,2-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCCC(=C)C1(O)C1OC(=O)C(=C)C1C(O)C2

InChI Identifier

InChI=1S/C15H20O4/c1-8-5-4-6-14(3)7-10(16)11-9(2)13(17)19-12(11)15(8,14)18/h10-12,16,18H,1-2,4-7H2,3H3

InChI Key

CMVJNYSIDKGGLC-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
Tertiary 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

Exogenous (HMDB: HMDB0302708)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

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	0.89	ALOGPS
logP	1.32	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	6.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	27.92 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]+	162.608	32859911
AllCCS	[M+H-H2O]+	159.035	32859911
AllCCS	[M+Na]+	166.877	32859911
AllCCS	[M+NH4]+	165.923	32859911
AllCCS	[M-H]-	165.821	32859911
AllCCS	[M+Na-2H]-	165.73	32859911
AllCCS	[M+HCOO]-	165.748	32859911
DeepCCS	[M-2H]-	196.903	30932474
DeepCCS	[M+Na]+	172.286	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 - Rothin B 10V, Positive-QTOF	splash10-00kb-0190000000-18de7627c4a23b562e11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 20V, Positive-QTOF	splash10-00mk-3490000000-72225e38c470c79e4e8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 40V, Positive-QTOF	splash10-0zfr-9310000000-e3b0722f4284fef5fdb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 10V, Negative-QTOF	splash10-03di-0090000000-534532b63306b2e231c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 20V, Negative-QTOF	splash10-03xs-1090000000-b318a376a68cbc476df7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 40V, Negative-QTOF	splash10-106u-5950000000-b2e2f55e2d356b5777f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 10V, Positive-QTOF	splash10-014j-0090000000-b795dd6f6b1f0257e396	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 20V, Positive-QTOF	splash10-0092-0980000000-fddbb5d63cb5b75e14d3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 40V, Positive-QTOF	splash10-004i-3910000000-7d4f3ed8358b5309ac1c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 10V, Negative-QTOF	splash10-03di-0190000000-3e36953ae971fa9eecc1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 20V, Negative-QTOF	splash10-03di-0190000000-cdf4c1c3b0d1bea934b4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rothin B 40V, Negative-QTOF	splash10-006x-3930000000-43eae1280d44f0701abb	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

FDB005896

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Rothin B (HMDB0302708)

MOL for HMDB0302708 (Rothin B)

3D MOL for HMDB0302708 (Rothin B)

3D SDF for HMDB0302708 (Rothin B)

3D-SDF for HMDB0302708 (Rothin B)

PDB for HMDB0302708 (Rothin B)

3D PDB for HMDB0302708 (Rothin B)

SMILES for HMDB0302708 (Rothin B)

INCHI for HMDB0302708 (Rothin B)

Structure for HMDB0302708 (Rothin B)

3D Structure for HMDB0302708 (Rothin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra