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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:36:17 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035596

Secondary Accession Numbers

HMDB35596

Metabolite Identification

Common Name

Armexifolin

Description

Armexifolin 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 Armexifolin.

Structure

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

HMDB0035596
     RDKit          3D
Armexifolin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.1208   -1.2318    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741   -0.4758    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0305    0.8585    1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    1.4740    1.7186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.3168    1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617    0.6373    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    0.5822   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.5895    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856    2.8123    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    1.5368    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    2.5888    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478    0.2113    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -0.9172    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6453   -1.1636    1.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.5803   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.2444   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438   -1.8079   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -1.5852   -0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -0.7880    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -2.2027   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323   -0.9656    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    0.9062   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    3.6414    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816    2.5848    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    3.1558    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    0.1666    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    0.1348   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155   -1.8473   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -0.3386    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.3648   -2.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.3335   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -1.1721   -2.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -2.3090   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -2.5556   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.9893   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -2.5688   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.1526    1.2980 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  2  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
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 05061308342D          

 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  2  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>
HMDB0035596

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h9,11,13,17H,1,4-6H2,2-3H3

> <INCHI_KEY>
QPXLDBMZJNDASA-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.961166048063276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
1.6701043186666664

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.480675068255874

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.442492694225493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.04085969525143

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
68.904

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035596
     RDKit          3D
Armexifolin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.1208   -1.2318    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741   -0.4758    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0305    0.8585    1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    1.4740    1.7186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.3168    1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617    0.6373    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    0.5822   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.5895    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856    2.8123    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    1.5368    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    2.5888    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478    0.2113    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -0.9172    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6453   -1.1636    1.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.5803   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.2444   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438   -1.8079   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -1.5852   -0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -0.7880    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -2.2027   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323   -0.9656    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    0.9062   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    3.6414    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816    2.5848    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    3.1558    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    0.1666    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    0.1348   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155   -1.8473   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -0.3386    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.3648   -2.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.3335   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -1.1721   -2.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -2.3090   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -2.5556   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.9893   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -2.5688   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.1526    1.2980 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  2  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
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  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    HMDB0035596
HETATM    1  C1  UNL     1       4.121  -1.232   0.364  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.074  -0.476   0.630  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.031   0.858   1.227  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.026   1.474   1.719  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.695   1.317   1.152  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.162   0.637   0.047  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.276   0.582  -0.082  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.012   1.590   0.339  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.386   2.812   0.958  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.475   1.537   0.210  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.137   2.589   0.034  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.148   0.211   0.293  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.143  -0.917   0.241  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.645  -1.164   1.528  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.962  -0.580  -0.683  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.582  -0.244  -2.023  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.144  -1.808  -0.848  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.355  -1.585  -0.831  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.645  -0.788   0.389  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.948  -2.203  -0.085  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.132  -0.966   0.555  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.694   0.906  -0.899  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.125   3.641   0.884  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.082   2.585   1.977  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.493   3.156   0.368  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.680   0.167   1.287  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.922   0.135  -0.487  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.615  -1.847  -0.097  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.792  -0.339   2.046  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.870   0.365  -2.632  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.506   0.334  -1.937  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.803  -1.172  -2.587  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.369  -2.309  -1.811  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.359  -2.556  -0.044  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.684  -0.989  -1.716  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.844  -2.569  -0.785  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.129  -1.153   1.298  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   11   12
CONECT   12   13   26   27
CONECT   13   14   15   28
CONECT   14   29
CONECT   15   16   17
CONECT   16   30   31   32
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   37
END

HMDB0035596
     RDKit          3D
Armexifolin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.1208   -1.2318    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741   -0.4758    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0305    0.8585    1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    1.4740    1.7186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.3168    1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617    0.6373    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    0.5822   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.5895    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856    2.8123    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    1.5368    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    2.5888    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478    0.2113    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -0.9172    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6453   -1.1636    1.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.5803   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.2444   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438   -1.8079   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -1.5852   -0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -0.7880    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -2.2027   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323   -0.9656    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    0.9062   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    3.6414    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816    2.5848    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    3.1558    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    0.1666    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    0.1348   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155   -1.8473   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915   -0.3386    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.3648   -2.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.3335   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -1.1721   -2.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -2.3090   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -2.5556   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.9893   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -2.5688   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.1526    1.2980 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  2  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
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Epi-ludovicin C	HMDB
1-Epiludovicin C	HMDB
[3AS-(3aalpha,5abeta,6beta,9bbeta)]-3a,5,5a,6,7,9b-hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2,8(3H,4H)-dione	HMDB

Chemical Formula

C₁₅H₁₈O₄

Average Molecular Weight

262.301

Monoisotopic Molecular Weight

262.120509064

IUPAC Name

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

Traditional Name

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

CAS Registry Number

64929-15-3

SMILES

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

InChI Identifier

InChI=1S/C15H18O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h9,11,13,17H,1,4-6H2,2-3H3

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035596)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035596)

Source

Endogenous

Endogenous (HMDB: HMDB0035596)

Plant

Plant (HMDB: HMDB0035596)

Animal

Animal (HMDB: HMDB0035596)

Exogenous

Food

Food (HMDB: HMDB0035596)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035596)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035596)

Cellular process

Cell signaling (HMDB: HMDB0035596)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035596)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035596)

Nutrient

Nutrient (HMDB: HMDB0035596)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035596)

Emulsifier (HMDB: HMDB0035596)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	201 - 203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	27140 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.84 g/L	ALOGPS
logP	0.63	ALOGPS
logP	1.67	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.9 m³·mol⁻¹	ChemAxon
Polarizability	26.96 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]+	163.102	31661259
DarkChem	[M-H]-	158.063	31661259
DeepCCS	[M+H]+	162.797	30932474
DeepCCS	[M-H]-	160.439	30932474
DeepCCS	[M-2H]-	193.325	30932474
DeepCCS	[M+Na]+	168.89	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.2	32859911
AllCCS	[M+Na]+	165.2	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	165.3	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Armexifolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1=O	3350.4	Standard polar	33892256
Armexifolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1=O	2135.4	Standard non polar	33892256
Armexifolin	CC1=C2C3OC(=O)C(=C)C3CCC2(C)C(O)CC1=O	2389.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Armexifolin,1TMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(=O)CC(O[Si](C)(C)C)C3(C)CCC12	2337.5	Semi standard non polar	33892256
Armexifolin,1TMS,isomer #2	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C)=CC(O)C3(C)CCC12	2387.9	Semi standard non polar	33892256
Armexifolin,2TMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)C3(C)CCC12	2411.5	Semi standard non polar	33892256
Armexifolin,2TMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)C3(C)CCC12	2195.7	Standard non polar	33892256
Armexifolin,1TBDMS,isomer #1	C=C1C(=O)OC2C3=C(C)C(=O)CC(O[Si](C)(C)C(C)(C)C)C3(C)CCC12	2559.8	Semi standard non polar	33892256
Armexifolin,1TBDMS,isomer #2	C=C1C(=O)OC2C3=C(C)C(O[Si](C)(C)C(C)(C)C)=CC(O)C3(C)CCC12	2589.3	Semi standard non polar	33892256
Armexifolin,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	2835.4	Semi standard non polar	33892256
Armexifolin,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	2610.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Armexifolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xu-2980000000-4ca9118be40190ac58be	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armexifolin GC-MS (1 TMS) - 70eV, Positive	splash10-00xu-3192000000-c510f76cd3bda309dacf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armexifolin 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 - Armexifolin 10V, Positive-QTOF	splash10-01ot-0290000000-9b19184ee1cf2cf59c5e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 20V, Positive-QTOF	splash10-01ot-0980000000-0c94b4b0092cd60afe9d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 40V, Positive-QTOF	splash10-0gb9-7910000000-7f0551b78d28bce27f14	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 10V, Negative-QTOF	splash10-03di-0090000000-d26fbae955b08a90028a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 20V, Negative-QTOF	splash10-03xu-0190000000-0ee5a1aa5d170c628a3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 40V, Negative-QTOF	splash10-0uy1-2940000000-e07bcb34e59ebe720f5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 10V, Positive-QTOF	splash10-03dl-0890000000-527d48fb87d02bc1e22d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 20V, Positive-QTOF	splash10-0006-0940000000-9bb1c1b3c4db36220995	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 40V, Positive-QTOF	splash10-000l-0910000000-baf1aa88cb99bdbeb1ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 10V, Negative-QTOF	splash10-02t9-0090000000-4fd8b99d59d84f8875b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 20V, Negative-QTOF	splash10-014i-0390000000-d5363cedd5bf3e29a571	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armexifolin 40V, Negative-QTOF	splash10-0a4i-3490000000-ce7839b7f577271afaff	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB014288

KNApSAcK ID

C00013062

Chemspider ID

26503148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13918461

PDB ID

Not Available

ChEBI ID

174461

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1850521

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 ]
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Showing metabocard for Armexifolin (HMDB0035596)

MOL for HMDB0035596 (Armexifolin)

3D MOL for HMDB0035596 (Armexifolin)

3D SDF for HMDB0035596 (Armexifolin)

3D-SDF for HMDB0035596 (Armexifolin)

PDB for HMDB0035596 (Armexifolin)

3D PDB for HMDB0035596 (Armexifolin)

SMILES for HMDB0035596 (Armexifolin)

INCHI for HMDB0035596 (Armexifolin)

Structure for HMDB0035596 (Armexifolin)

3D Structure for HMDB0035596 (Armexifolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra