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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:56:58 UTC

Update Date

2022-03-07 02:54:41 UTC

HMDB ID

HMDB0035903

Secondary Accession Numbers

HMDB35903

Metabolite Identification

Common Name

Enokipodin A

Description

Enokipodin A, also known as avarol, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Enokipodin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, enokipodin a has been detected, but not quantified in, mushrooms. This could make enokipodin a a potential biomarker for the consumption of these foods.

Structure

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

HMDB0035903
     RDKit          3D
Enokipodin A
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.5855   -0.1853   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.1576   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.1266   -1.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -0.1013   -1.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.1058    0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444   -0.1363    1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -0.1614    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784   -0.1920    1.6592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -0.0793    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.5049    2.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057   -1.4944    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542   -1.6602   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -0.3226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -0.0898   -2.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -0.0698   -1.9400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    0.6199   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    2.0104   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.6606    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148    0.8804   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914   -0.6684   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.6894   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -0.1222   -2.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -0.1405    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -0.1965    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    1.3046    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -0.2535    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8649    0.9908    2.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1672    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -1.6764    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6755   -2.1208   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.4134   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6267   -0.7590   -2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    2.0455   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    2.5550   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720    2.5168    0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    1.6920    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.2558    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.0531   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 16  9  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 02241215332D          

 18 20  0  0  0  0            999 V2000
   -1.2595    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -0.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452   -0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679   -0.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6174   -0.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -0.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6174    0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4004    1.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466    0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -1.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753   -0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    0.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 18  1  0  0  0  0
  2  3  2  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035903

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-7-12-10(8-11(9)16)14(4)5-6-15(17,18-12)13(14,2)3/h7-8,16-17H,5-6H2,1-4H3

> <INCHI_KEY>
KANVQRLDTGOSBL-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.475076506958278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.452345026333333

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.570636804032754

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.190204653201718

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3216990441763015

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
69.46459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035903
     RDKit          3D
Enokipodin A
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.5855   -0.1853   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.1576   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.1266   -1.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -0.1013   -1.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.1058    0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444   -0.1363    1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -0.1614    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784   -0.1920    1.6592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -0.0793    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.5049    2.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057   -1.4944    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542   -1.6602   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -0.3226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -0.0898   -2.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -0.0698   -1.9400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    0.6199   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    2.0104   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.6606    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148    0.8804   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914   -0.6684   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.6894   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -0.1222   -2.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -0.1405    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -0.1965    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    1.3046    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -0.2535    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8649    0.9908    2.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1672    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -1.6764    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6755   -2.1208   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.4134   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6267   -0.7590   -2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    2.0455   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    2.5550   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720    2.5168    0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    1.6920    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.2558    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.0531   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 16  9  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.351   0.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.351  -0.861   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.018  -1.632   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.313  -0.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.313   0.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.018   1.449   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.518  -1.822   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.019  -1.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.687  -0.095   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.019   1.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.518   1.634   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.747   2.970   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.518   0.093   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.838  -0.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.700   0.093   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.417  -2.970   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.687  -1.632   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.687   1.452   0.000  0.00  0.00           O+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   11                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13   16                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    5   10   12   13                                             
CONECT   12   11                                                            
CONECT   13    8   11   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8                                                            
CONECT   17    2                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0035903
HETATM    1  C1  UNL     1       4.585  -0.185  -1.072  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.166  -0.158  -0.601  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.100  -0.127  -1.481  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.799  -0.101  -1.036  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.509  -0.106   0.303  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.544  -0.136   1.208  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.842  -0.161   0.744  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.878  -0.192   1.659  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.884  -0.079   0.830  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.926   0.505   2.188  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.406  -1.494   0.743  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.654  -1.660  -0.729  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.557  -0.323  -1.378  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.586  -0.090  -2.260  1.00  0.00           O  
HETATM   15  O3  UNL     1      -0.282  -0.070  -1.940  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.750   0.620  -0.183  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.278   2.010  -0.496  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.190   0.661   0.245  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.915   0.880  -1.093  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.691  -0.668  -2.047  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.183  -0.689  -0.290  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.303  -0.122  -2.563  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.333  -0.141   2.294  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.719  -0.197   2.644  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.130   1.305   2.242  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.615  -0.253   2.935  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.865   0.991   2.470  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.546  -2.167   1.012  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.292  -1.676   1.365  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.675  -2.121  -0.833  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.965  -2.413  -1.196  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.627  -0.759  -2.986  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.428   2.045  -1.181  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.115   2.555  -0.975  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.072   2.517   0.465  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.600   1.692   0.227  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.337   0.256   1.258  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.785   0.053  -0.494  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   15
CONECT    5    6    9
CONECT    6    7    7   23
CONECT    7    8
CONECT    8   24
CONECT    9   10   11   16
CONECT   10   25   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15   16
CONECT   14   32
CONECT   16   17   18
CONECT   17   33   34   35
CONECT   18   36   37   38
END

HMDB0035903
     RDKit          3D
Enokipodin A
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.5855   -0.1853   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.1576   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.1266   -1.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -0.1013   -1.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.1058    0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444   -0.1363    1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -0.1614    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784   -0.1920    1.6592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -0.0793    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.5049    2.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057   -1.4944    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542   -1.6602   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -0.3226   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -0.0898   -2.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -0.0698   -1.9400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    0.6199   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    2.0104   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.6606    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148    0.8804   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914   -0.6684   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.6894   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -0.1222   -2.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3327   -0.1405    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -0.1965    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    1.3046    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -0.2535    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8649    0.9908    2.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1672    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -1.6764    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6755   -2.1208   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.4134   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6267   -0.7590   -2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    2.0455   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    2.5550   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720    2.5168    0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    1.6920    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.2558    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.0531   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 16  9  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Avarol	HMDB
Enokipodin a	MeSH

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol

Traditional Name

1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol

CAS Registry Number

306951-07-5

SMILES

CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C

InChI Identifier

InChI=1S/C15H20O3/c1-9-7-12-10(8-11(9)16)14(4)5-6-15(17,18-12)13(14,2)3/h7-8,16-17H,5-6H2,1-4H3

InChI Key

KANVQRLDTGOSBL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Hemiacetal
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035903)

Cellular substructure

Membrane (HMDB: HMDB0035903)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035903)

Source

Exogenous

Food

Food (HMDB: HMDB0035903)

Plant (HMDB: HMDB0035903)

Not Available

Nutrient (HMDB: HMDB0035903)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138.5 - 138.9 °C	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	0.42 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.45	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.46 m³·mol⁻¹	ChemAxon
Polarizability	27.48 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]+	155.867	31661259
DarkChem	[M-H]-	155.427	31661259
DeepCCS	[M+H]+	164.636	30932474
DeepCCS	[M-H]-	162.278	30932474
DeepCCS	[M-2H]-	195.164	30932474
DeepCCS	[M+Na]+	170.729	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.9	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Enokipodin A	CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C	3116.9	Standard polar	33892256
Enokipodin A	CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C	1980.6	Standard non polar	33892256
Enokipodin A	CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C	2057.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Enokipodin A,1TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCC(O)(O2)C1(C)C	2079.4	Semi standard non polar	33892256
Enokipodin A,1TMS,isomer #2	CC1=CC2=C(C=C1O)C1(C)CCC(O[Si](C)(C)C)(O2)C1(C)C	2025.7	Semi standard non polar	33892256
Enokipodin A,2TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCC(O[Si](C)(C)C)(O2)C1(C)C	2089.7	Semi standard non polar	33892256
Enokipodin A,1TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC(O)(O2)C1(C)C	2363.2	Semi standard non polar	33892256
Enokipodin A,1TBDMS,isomer #2	CC1=CC2=C(C=C1O)C1(C)CCC(O[Si](C)(C)C(C)(C)C)(O2)C1(C)C	2314.3	Semi standard non polar	33892256
Enokipodin A,2TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)(O2)C1(C)C	2622.1	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 - Enokipodin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2490000000-2cf3034e97b3b0000e1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enokipodin A GC-MS (2 TMS) - 70eV, Positive	splash10-004i-5109000000-1830e9b3dc94ee03cd21	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enokipodin A 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 - Enokipodin A 10V, Positive-QTOF	splash10-0002-0190000000-6b3131112da3f69c3cb6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 20V, Positive-QTOF	splash10-0002-0790000000-ec951199fc6a8f30a0ff	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 40V, Positive-QTOF	splash10-0zmi-9720000000-c4b8b0eed0bf42b74a0b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 10V, Negative-QTOF	splash10-0002-0290000000-19a854b5f932db85ac71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 20V, Negative-QTOF	splash10-0002-0290000000-11652c6a6135dce21dd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 40V, Negative-QTOF	splash10-0a4i-3930000000-036665e036ad304fc2cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 20V, Negative-QTOF	splash10-0002-0090000000-3c5fa023f431202efe2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 40V, Negative-QTOF	splash10-00di-0930000000-ab8db158a47aa0509b1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 10V, Positive-QTOF	splash10-001j-0090000000-21a321c486f0c8463d19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 20V, Positive-QTOF	splash10-00dj-0790000000-f28d6a1afee8fb61273d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enokipodin A 40V, Positive-QTOF	splash10-05r3-9310000000-1461b423e32a6b290f15	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014688

KNApSAcK ID

Not Available

Chemspider ID

10190206

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578749

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Enokipodin A (HMDB0035903)

MOL for HMDB0035903 (Enokipodin A)

3D MOL for HMDB0035903 (Enokipodin A)

3D SDF for HMDB0035903 (Enokipodin A)

3D-SDF for HMDB0035903 (Enokipodin A)

PDB for HMDB0035903 (Enokipodin A)

3D PDB for HMDB0035903 (Enokipodin A)

SMILES for HMDB0035903 (Enokipodin A)

INCHI for HMDB0035903 (Enokipodin A)

Structure for HMDB0035903 (Enokipodin A)

3D Structure for HMDB0035903 (Enokipodin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra