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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:01 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036135

Secondary Accession Numbers

HMDB36135

Metabolite Identification

Common Name

3-Epiarmefolin

Description

3-Epiarmefolin 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. Based on a literature review a small amount of articles have been published on 3-Epiarmefolin.

Structure

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

HMDB0036135
     RDKit          3D
3-Epiarmefolin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.5571   -0.3378    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.0334   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161    1.0984   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.7962   -1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.2149   -1.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.7431    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    0.4661    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    1.4913   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    2.8951   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    1.2653   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    2.2510   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -0.0371   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -1.1337   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.3615   -0.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615   -0.9323    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791   -1.3913    1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258   -1.7607   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -1.6879   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0148   -0.4639    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    0.1111   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300   -1.1494    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    1.4816    1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    3.0444    0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2097   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501    3.6047    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.1011    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367    3.0582   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    0.0608   -1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8071   -0.2356   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -1.2475    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514   -2.4479   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -1.3981    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -2.4477    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.7353    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279   -1.3159   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -2.8065   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586   -1.7228   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -2.6339    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583   -0.6795    1.5439 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 15  7  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv0541 05061308542D          

 19 21  0  0  0  0            999 V2000
    4.2295    1.3982    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
    0.7591    1.8407    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
    1.5837    1.8150    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
    3.5995    0.8656    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
    2.7983    1.0622    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
    0.3245    1.1395    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
    2.3637    0.3610    0.0000 C   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
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   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
    4.3613   -0.3918    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
  5  4  1  0  0  0  0
  7  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036135

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h9-11,13,16-17H,1,4-6H2,2-3H3

> <INCHI_KEY>
VRHFGDDYTIJYIX-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.691031374442588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.8778751470000002

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.933697404439634

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.229106545217189

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9960442741739532

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.8367

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-5a,9-dimethyl-3-methylidene-3aH,4H,5H,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036135
     RDKit          3D
3-Epiarmefolin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.5571   -0.3378    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.0334   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161    1.0984   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.7962   -1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.2149   -1.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.7431    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    0.4661    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    1.4913   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    2.8951   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    1.2653   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    2.2510   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -0.0371   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -1.1337   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.3615   -0.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615   -0.9323    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791   -1.3913    1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258   -1.7607   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -1.6879   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0148   -0.4639    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    0.1111   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300   -1.1494    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    1.4816    1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    3.0444    0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2097   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501    3.6047    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.1011    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367    3.0582   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    0.0608   -1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8071   -0.2356   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -1.2475    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514   -2.4479   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -1.3981    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -2.4477    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.7353    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279   -1.3159   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -2.8065   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586   -1.7228   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -2.6339    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583   -0.6795    1.5439 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 15  7  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  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       7.895   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790  -1.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.417   3.436   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       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.719   1.616   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       5.223   1.983   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       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   15                                                       
CONECT    6   10   11                                                       
CONECT    7    1    9   14                                                  
CONECT    8    2   10   12                                                  
CONECT    9    4    7   13                                                  
CONECT   10    6    8   16                                                  
CONECT   11    6   15   17                                                  
CONECT   12    8   13   15                                                  
CONECT   13    9   12   19                                                  
CONECT   14    7   18   19                                                  
CONECT   15    3    5   11   12                                             
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036135
HETATM    1  C1  UNL     1       4.557  -0.338   0.271  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.331   0.033  -0.030  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.016   1.098  -0.971  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.866   1.796  -1.601  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.612   1.215  -1.058  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.157   0.743   0.220  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.280   0.466   0.146  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.093   1.491  -0.085  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.638   2.895  -0.270  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.587   1.265  -0.178  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.214   2.251  -0.893  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.734  -0.037  -0.975  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.169  -1.134  -0.142  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.293  -2.361  -0.829  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.762  -0.932   0.328  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.679  -1.391   1.745  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.126  -1.761  -0.602  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.574  -1.688  -0.281  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.015  -0.464   0.446  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.416   0.111  -0.150  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.730  -1.149   0.991  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.430   1.482   1.019  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.419   3.044   0.004  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.807   3.210  -1.323  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.250   3.605   0.347  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.998   1.101   0.819  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.437   3.058  -0.344  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.271   0.061  -1.979  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.807  -0.236  -1.124  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.857  -1.247   0.743  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.251  -2.448  -1.098  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.694  -1.398   2.191  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.299  -2.448   1.735  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.075  -0.735   2.402  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.028  -1.316  -1.618  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.228  -2.806  -0.662  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.159  -1.723  -1.248  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.883  -2.634   0.247  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.158  -0.680   1.544  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   22
CONECT    7    8    8   15
CONECT    8    9   10
CONECT    9   23   24   25
CONECT   10   11   12   26
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   15   30
CONECT   14   31
CONECT   15   16   17
CONECT   16   32   33   34
CONECT   17   18   35   36
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0036135
     RDKit          3D
3-Epiarmefolin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.5571   -0.3378    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.0334   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161    1.0984   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.7962   -1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.2149   -1.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.7431    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    0.4661    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    1.4913   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    2.8951   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    1.2653   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    2.2510   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -0.0371   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -1.1337   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930   -2.3615   -0.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615   -0.9323    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6791   -1.3913    1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258   -1.7607   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -1.6879   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0148   -0.4639    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    0.1111   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300   -1.1494    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    1.4816    1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    3.0444    0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2097   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501    3.6047    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.1011    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367    3.0582   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    0.0608   -1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8071   -0.2356   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -1.2475    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514   -2.4479   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943   -1.3981    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -2.4477    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.7353    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279   -1.3159   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279   -2.8065   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586   -1.7228   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -2.6339    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583   -0.6795    1.5439 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 15  7  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

6,8-dihydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

Traditional Name

6,8-dihydroxy-5a,9-dimethyl-3-methylidene-3aH,4H,5H,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

CAS Registry Number

293313-26-5

SMILES

CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1O

InChI Identifier

InChI=1S/C15H20O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h9-11,13,16-17H,1,4-6H2,2-3H3

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036135)

Source

Endogenous

Endogenous (HMDB: HMDB0036135)

Plant

Plant (HMDB: HMDB0036135)

Animal

Animal (HMDB: HMDB0036135)

Exogenous

Food

Food (HMDB: HMDB0036135)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036135)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036135)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036135)

Lipid metabolism pathway (HMDB: HMDB0036135)

Cellular process

Cell signaling (HMDB: HMDB0036135)

Biochemical process

Lipid transport (HMDB: HMDB0036135)

Role

Biological role

Energy source (HMDB: HMDB0036135)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036135)

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
Water Solubility	5.08 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.88	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-3	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	69.84 m³·mol⁻¹	ChemAxon
Polarizability	27.69 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
DarkChem	[M+H]+	163.226	31661259
DarkChem	[M-H]-	158.543	31661259
DeepCCS	[M+H]+	163.458	30932474
DeepCCS	[M-H]-	161.1	30932474
DeepCCS	[M-2H]-	194.075	30932474
DeepCCS	[M+Na]+	169.551	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Epiarmefolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1O	3423.3	Standard polar	33892256
3-Epiarmefolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1O	2203.5	Standard non polar	33892256
3-Epiarmefolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1O	2346.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Epiarmefolin,1TMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O)CC(O[Si](C)(C)C)C3(C)CCC12	2347.0	Semi standard non polar	33892256
3-Epiarmefolin,1TMS,isomer #2	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C)CC(O)C3(C)CCC12	2337.6	Semi standard non polar	33892256
3-Epiarmefolin,2TMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C)CC(O[Si](C)(C)C)C3(C)CCC12	2348.0	Semi standard non polar	33892256
3-Epiarmefolin,1TBDMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O)CC(O[Si](C)(C)C(C)(C)C)C3(C)CCC12	2570.8	Semi standard non polar	33892256
3-Epiarmefolin,1TBDMS,isomer #2	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C(C)(C)C)CC(O)C3(C)CCC12	2550.9	Semi standard non polar	33892256
3-Epiarmefolin,2TBDMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C3(C)CCC12	2775.9	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 - 3-Epiarmefolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0690000000-17005d7adcee20bf4fd4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epiarmefolin GC-MS (2 TMS) - 70eV, Positive	splash10-0006-3049000000-2bc517e16e8db5a631e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epiarmefolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epiarmefolin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 10V, Positive-QTOF	splash10-00kb-0190000000-e20f7a1208be5b89484c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 20V, Positive-QTOF	splash10-002b-0980000000-82837585fdddf3c89abf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 40V, Positive-QTOF	splash10-0ufr-6930000000-d73a01e839d905af078a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 10V, Negative-QTOF	splash10-03di-0090000000-8ac1b80a3ccbc13bd426	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 20V, Negative-QTOF	splash10-0292-0190000000-8d08fc44cd028ffe04eb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 40V, Negative-QTOF	splash10-0uxu-3980000000-41c3d78030e3ddcdb0bf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 20V, Negative-QTOF	splash10-03di-0190000000-eb352fa891343867b00b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 40V, Negative-QTOF	splash10-03di-2490000000-8075882a9dc307380161	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 10V, Positive-QTOF	splash10-014m-0490000000-b3332a2230806b3ea5a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 20V, Positive-QTOF	splash10-00my-0960000000-9df01454210ee4e7e823	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epiarmefolin 40V, Positive-QTOF	splash10-0076-1910000000-669b7e4d62ef8325bbb4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014984

KNApSAcK ID

Not Available

Chemspider ID

35014102

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13944253

PDB ID

Not Available

ChEBI ID

172036

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

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Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Epiarmefolin (HMDB0036135)

MOL for HMDB0036135 (3-Epiarmefolin)

3D MOL for HMDB0036135 (3-Epiarmefolin)

3D SDF for HMDB0036135 (3-Epiarmefolin)

3D-SDF for HMDB0036135 (3-Epiarmefolin)

PDB for HMDB0036135 (3-Epiarmefolin)

3D PDB for HMDB0036135 (3-Epiarmefolin)

SMILES for HMDB0036135 (3-Epiarmefolin)

INCHI for HMDB0036135 (3-Epiarmefolin)

Structure for HMDB0036135 (3-Epiarmefolin)

3D Structure for HMDB0036135 (3-Epiarmefolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra