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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:28:09 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038188

Secondary Accession Numbers

HMDB38188

Metabolite Identification

Common Name

Curcolone

Description

Curcolone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on Curcolone.

Structure

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

HMDB0038188
     RDKit          3D
Curcolone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.6559    2.6162    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    1.4043    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    0.5628    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    0.8089    0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.9450    0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -0.3354    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2595   -0.4814   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.6440   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -1.8431   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -2.4552   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538   -1.5980    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -1.8194    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -0.6837   -0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.6454   -2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.9532   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -1.8804    0.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.2491   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.1976    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    2.2977    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    3.0666    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445    3.3694    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.5028   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    0.3641   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    0.9370    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4977   -2.2969   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -1.9482    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -2.7465   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -1.2733   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716    0.3927   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -1.0984   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -1.4704   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310   -1.5113    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.0707   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763    0.8259   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.1675    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    0.7592    1.7854 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 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  2  1  0
 13  3  1  0
 11  6  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
M  END

  Mrv0541 05061310172D          

 18 20  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038188

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1C(=O)C1=C(C)CCC(O)C1(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-4-5-11(16)15(3)6-10-12(9(2)7-18-10)14(17)13(8)15/h7,11,16H,4-6H2,1-3H3

> <INCHI_KEY>
PFIXJSCFTAVWBW-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.830245144968735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3,5,8a-trimethyl-4H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-one

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
2.1172870690000005

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.606756307019054

> <JCHEM_PKA_STRONGEST_BASIC>
-2.85350307595353

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
69.5842

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3,5,8a-trimethyl-6H,7H,8H,9H-naphtho[2,3-b]furan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038188
     RDKit          3D
Curcolone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.6559    2.6162    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    1.4043    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    0.5628    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    0.8089    0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.9450    0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -0.3354    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2595   -0.4814   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.6440   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -1.8431   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -2.4552   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538   -1.5980    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -1.8194    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -0.6837   -0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.6454   -2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.9532   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -1.8804    0.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.2491   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.1976    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    2.2977    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    3.0666    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445    3.3694    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.5028   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    0.3641   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    0.9370    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4977   -2.2969   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -1.9482    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -2.7465   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -1.2733   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716    0.3927   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -1.0984   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -1.4704   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310   -1.5113    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.0707   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763    0.8259   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.1675    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    0.7592    1.7854 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 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  2  1  0
 13  3  1  0
 11  6  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   5.791   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.466   4.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.466   1.834   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6   10   15                                                       
CONECT    7    9   18                                                       
CONECT    8    1    4   13                                                  
CONECT    9    2    7   12                                                  
CONECT   10    6   12   18                                                  
CONECT   11    5   15   16                                                  
CONECT   12    9   10   14                                                  
CONECT   13    8   14   15                                                  
CONECT   14   12   13   17                                                  
CONECT   15    3    6   11   13                                             
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0038188
HETATM    1  C1  UNL     1      -0.656   2.616   1.380  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.263   1.404   0.742  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.491   0.563   0.158  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.985   0.809   0.129  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.457   1.945   0.171  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.885  -0.335   0.049  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.260  -0.481  -0.037  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.216   0.644  -0.027  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.519  -1.843  -0.129  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.366  -2.455  -0.098  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.354  -1.598   0.009  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.105  -1.819   0.085  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.868  -0.684  -0.540  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.442  -0.645  -2.005  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.342  -0.953  -0.422  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.580  -1.880   0.590  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.202   0.249  -0.285  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.732   1.198   0.788  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.154   2.298   2.076  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.437   3.067   2.023  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.345   3.369   0.649  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.734   1.503  -0.538  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.169   0.364  -0.541  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.408   0.937   1.014  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.498  -2.297  -0.211  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.414  -1.948   1.164  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.330  -2.746  -0.489  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.154  -1.273  -2.578  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.372   0.393  -2.373  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.564  -1.098  -2.128  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.642  -1.470  -1.380  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.431  -1.511   1.488  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.228  -0.071  -0.036  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.276   0.826  -1.230  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.265   2.168   0.745  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.991   0.759   1.785  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   13
CONECT    4    5    5    6
CONECT    6    7   11   11
CONECT    7    8    9    9
CONECT    8   22   23   24
CONECT    9   10   25
CONECT   10   11
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   15
CONECT   14   28   29   30
CONECT   15   16   17   31
CONECT   16   32
CONECT   17   18   33   34
CONECT   18   35   36
END

HMDB0038188
     RDKit          3D
Curcolone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.6559    2.6162    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    1.4043    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    0.5628    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    0.8089    0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.9450    0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -0.3354    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2595   -0.4814   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.6440   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -1.8431   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -2.4552   -0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538   -1.5980    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -1.8194    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -0.6837   -0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.6454   -2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.9532   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -1.8804    0.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022    0.2491   -0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.1976    0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537    2.2977    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    3.0666    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445    3.3694    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.5028   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    0.3641   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4076    0.9370    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4977   -2.2969   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -1.9482    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -2.7465   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -1.2733   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716    0.3927   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -1.0984   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -1.4704   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310   -1.5113    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.0707   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763    0.8259   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.1675    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    0.7592    1.7854 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 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  2  1  0
 13  3  1  0
 11  6  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8S-cis)-7,8,8a,9-tetrahydro-8-Hydroxy-3,5,8a-trimethylnaphtho[2,3-b]furan-4(6H)-one	HMDB
1a-Hydroxyfuranoeudesm-4-en-6-one	HMDB
Nehipetol	HMDB

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

8-hydroxy-3,5,8a-trimethyl-4H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-one

Traditional Name

8-hydroxy-3,5,8a-trimethyl-6H,7H,8H,9H-naphtho[2,3-b]furan-4-one

CAS Registry Number

17015-43-9

SMILES

CC1=COC2=C1C(=O)C1=C(C)CCC(O)C1(C)C2

InChI Identifier

InChI=1S/C15H18O3/c1-8-4-5-11(16)15(3)6-10-12(9(2)7-18-10)14(17)13(8)15/h7,11,16H,4-6H2,1-3H3

InChI Key

PFIXJSCFTAVWBW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Furan
Heteroaromatic compound
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038188)

Source

Endogenous

Endogenous (HMDB: HMDB0038188)

Animal

Animal (HMDB: HMDB0038188)

Exogenous

Food

Food (HMDB: HMDB0038188)

Exogenous (HMDB: HMDB0038188)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038188)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038188)

Lipid metabolism pathway (HMDB: HMDB0038188)

Cellular process

Cell signaling (HMDB: HMDB0038188)

Biochemical process

Lipid transport (HMDB: HMDB0038188)

Role

Biological role

Energy source (HMDB: HMDB0038188)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 139.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	71.19 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	0.27 g/L	ALOGPS
logP	1.99	ALOGPS
logP	2.12	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.58 m³·mol⁻¹	ChemAxon
Polarizability	26.83 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]+	156.576	31661259
DarkChem	[M-H]-	150.215	31661259
DeepCCS	[M+H]+	162.972	30932474
DeepCCS	[M-H]-	160.614	30932474
DeepCCS	[M-2H]-	194.019	30932474
DeepCCS	[M+Na]+	169.235	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	160.0	32859911
AllCCS	[M+Na]+	161.0	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	163.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcolone	CC1=COC2=C1C(=O)C1=C(C)CCC(O)C1(C)C2	3132.2	Standard polar	33892256
Curcolone	CC1=COC2=C1C(=O)C1=C(C)CCC(O)C1(C)C2	1860.6	Standard non polar	33892256
Curcolone	CC1=COC2=C1C(=O)C1=C(C)CCC(O)C1(C)C2	2028.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcolone,1TMS,isomer #1	CC1=C2C(=O)C3=C(CC2(C)C(O[Si](C)(C)C)CC1)OC=C3C	2243.3	Semi standard non polar	33892256
Curcolone,1TBDMS,isomer #1	CC1=C2C(=O)C3=C(CC2(C)C(O[Si](C)(C)C(C)(C)C)CC1)OC=C3C	2482.2	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 - Curcolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uy0-1490000000-68796e8a22a5bd1253a2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcolone GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-7293000000-a7d5aab1f5c577d6388e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcolone 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 - Curcolone 10V, Positive-QTOF	splash10-004j-0090000000-d0f6c508bef006ed3cab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 20V, Positive-QTOF	splash10-004i-2690000000-ccc15b7f8bd6ddfd9ea5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 40V, Positive-QTOF	splash10-0ldl-9410000000-aaea24c3242c9f20f45a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 10V, Negative-QTOF	splash10-0002-0090000000-abfa9e53941888998435	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 20V, Negative-QTOF	splash10-0002-0190000000-34bc3cbe72e685fc0770	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 40V, Negative-QTOF	splash10-01pa-3960000000-52ec2753316c89a33d84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 10V, Negative-QTOF	splash10-0002-0090000000-851e47b490f6973ef9e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 20V, Negative-QTOF	splash10-0002-0090000000-5644195f6b74131b7492	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 40V, Negative-QTOF	splash10-0203-0590000000-6ba62d00fe0ab14686d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 10V, Positive-QTOF	splash10-0002-0090000000-7216d1413b7714a094f6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 20V, Positive-QTOF	splash10-0002-0290000000-32e34627e7be3316e76d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolone 40V, Positive-QTOF	splash10-001j-8910000000-55c8eed0a0c3dd575eba	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB017427

KNApSAcK ID

C00012940

Chemspider ID

4475311

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316208

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866221

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 Curcolone (HMDB0038188)

MOL for HMDB0038188 (Curcolone)

3D MOL for HMDB0038188 (Curcolone)

3D SDF for HMDB0038188 (Curcolone)

3D-SDF for HMDB0038188 (Curcolone)

PDB for HMDB0038188 (Curcolone)

3D PDB for HMDB0038188 (Curcolone)

SMILES for HMDB0038188 (Curcolone)

INCHI for HMDB0038188 (Curcolone)

Structure for HMDB0038188 (Curcolone)

3D Structure for HMDB0038188 (Curcolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra