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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:33:54 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036427

Secondary Accession Numbers

HMDB36427

Metabolite Identification

Common Name

Procurcumenol

Description

Procurcumenol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Based on a literature review a significant number of articles have been published on Procurcumenol.

Structure

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

HMDB0036427
     RDKit          3D
Procurcumenol
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.2848    3.4226   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    2.1623   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980    2.3262   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2455   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364    1.5427   -1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101   -0.0858    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -0.6966    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -0.1497    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712   -2.0733    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419   -0.8095    0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591   -0.3123   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.9555    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5271    1.0288   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -0.3815   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -1.2443   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1961    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478   -1.9595   -1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    3.5862   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1175    3.3169    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    4.2404    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380    3.3251   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -0.1299   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757   -0.8472    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.8550    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -2.8076    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -1.9823    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7775   -2.4280    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2608   -0.5120    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823   -1.8973    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322   -0.0770   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.8507    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    1.7467   -0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    1.2888   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -0.6201   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.4805    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197   -2.8054    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.6641    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -2.8902    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -2.8432   -1.5627 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  2  3
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12  2  1  0
 15 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061309082D          

 17 18  0  0  0  0            999 V2000
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -1.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085   -1.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036427

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)12-8-13-11(5-6-15(13,4)17)10(3)7-14(12)16/h7,11,13,17H,5-6,8H2,1-4H3

> <INCHI_KEY>
RHBOHEXDGUVIIY-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.19261406602455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3,8-dimethyl-5-(propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.7819444329999996

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.866575191253638

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.694200674738095

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6699935865499987

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.68379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-1,4-dimethyl-7-(propan-2-ylidene)-3,3a,8,8a-tetrahydro-2H-azulen-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036427
     RDKit          3D
Procurcumenol
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.2848    3.4226   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    2.1623   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980    2.3262   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2455   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364    1.5427   -1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101   -0.0858    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -0.6966    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -0.1497    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712   -2.0733    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419   -0.8095    0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591   -0.3123   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.9555    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5271    1.0288   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -0.3815   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -1.2443   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1961    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478   -1.9595   -1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    3.5862   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1175    3.3169    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    4.2404    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380    3.3251   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -0.1299   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757   -0.8472    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.8550    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -2.8076    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -1.9823    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7775   -2.4280    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2608   -0.5120    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823   -1.8973    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322   -0.0770   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.8507    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    1.7467   -0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    1.2888   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -0.6201   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.4805    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197   -2.8054    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.6641    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -2.8902    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -2.8432   -1.5627 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  2  3
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12  2  1  0
 15 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.243  -2.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.157  -4.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.915   2.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.216  -3.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.968  -0.384   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.256  -2.399   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7   10   14                                                       
CONECT    8   12   13                                                       
CONECT    9    1    2   12                                                  
CONECT   10    3    7   11                                                  
CONECT   11    5   10   13                                                  
CONECT   12    8    9   14                                                  
CONECT   13    8   11   15                                                  
CONECT   14    7   12   16                                                  
CONECT   15    4    6   13   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036427
HETATM    1  C1  UNL     1      -1.285   3.423  -0.037  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.493   2.162  -0.071  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.798   2.326  -0.324  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.805   1.245  -0.414  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.836   1.543  -1.070  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.710  -0.086   0.171  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.843  -0.697   0.390  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.185  -0.150   0.097  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.771  -2.073   0.990  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.442  -0.810   0.546  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.659  -0.312  -0.304  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.298   0.955   0.184  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.527   1.029  -0.716  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.041  -0.381  -0.652  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.801  -1.244  -0.515  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.032  -2.196   0.626  1.00  0.00           C  
HETATM   17  O2  UNL     1      -1.648  -1.959  -1.690  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.666   3.586  -1.061  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.117   3.317   0.705  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.596   4.240   0.244  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.138   3.325  -0.475  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.420  -0.130  -0.997  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.976  -0.847   0.509  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.302   0.855   0.565  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.387  -2.808   0.272  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.124  -1.982   1.890  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.777  -2.428   1.305  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.261  -0.512   1.617  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.582  -1.897   0.547  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.232  -0.077  -1.323  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.591   0.851   1.251  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.277   1.747  -0.324  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.160   1.289  -1.722  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.606  -0.620  -1.589  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.717  -0.480   0.208  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.920  -2.805   0.374  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.254  -1.664   1.565  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.198  -2.890   0.790  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.239  -2.843  -1.563  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   12
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7    7   10
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   25   26   27
CONECT   10   11   28   29
CONECT   11   12   15   30
CONECT   12   13   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   17
CONECT   16   36   37   38
CONECT   17   39
END

HMDB0036427
     RDKit          3D
Procurcumenol
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.2848    3.4226   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    2.1623   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980    2.3262   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.2455   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364    1.5427   -1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101   -0.0858    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -0.6966    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -0.1497    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712   -2.0733    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419   -0.8095    0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591   -0.3123   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.9555    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5271    1.0288   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -0.3815   -0.6525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -1.2443   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1961    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478   -1.9595   -1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6663    3.5862   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1175    3.3169    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    4.2404    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380    3.3251   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -0.1299   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757   -0.8472    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.8550    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -2.8076    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -1.9823    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7775   -2.4280    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2608   -0.5120    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823   -1.8973    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322   -0.0770   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.8507    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    1.7467   -0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    1.2888   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -0.6201   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.4805    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197   -2.8054    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.6641    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -2.8902    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -2.8432   -1.5627 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  2  3
  7  8  1  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12  2  1  0
 15 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Epiprocurcumenol	MeSH

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

3-hydroxy-3,8-dimethyl-5-(propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-one

Traditional Name

1-hydroxy-1,4-dimethyl-7-(propan-2-ylidene)-3,3a,8,8a-tetrahydro-2H-azulen-6-one

CAS Registry Number

21698-40-8

SMILES

CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)12-8-13-11(5-6-15(13,4)17)10(3)7-14(12)16/h7,11,13,17H,5-6,8H2,1-4H3

InChI Key

RHBOHEXDGUVIIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0036427)

Food

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Process

Not Available

Role

Biological role

Anti-inflammatory (HMDB: HMDB0036427)
Anti TNF (HMDB: HMDB0036427)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	360.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	117.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.130 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.78	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.69	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.68 m³·mol⁻¹	ChemAxon
Polarizability	27.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.092	31661259
DarkChem	[M-H]-	155.402	31661259
DeepCCS	[M+H]+	153.943	30932474
DeepCCS	[M-H]-	151.585	30932474
DeepCCS	[M-2H]-	185.171	30932474
DeepCCS	[M+Na]+	160.107	30932474
AllCCS	[M+H]+	153.4	32859911
AllCCS	[M+H-H2O]+	149.7	32859911
AllCCS	[M+NH4]+	156.9	32859911
AllCCS	[M+Na]+	157.9	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.01 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7856 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2247.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	308.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	532.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	651.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	67.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	984.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	402.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1168.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	268.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	435.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Procurcumenol	CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O	2723.4	Standard polar	33892256
Procurcumenol	CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O	1854.2	Standard non polar	33892256
Procurcumenol	CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O	1918.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Procurcumenol,1TMS,isomer #1	CC1=CC(=O)C(=C(C)C)CC2C1CCC2(C)O[Si](C)(C)C	1990.3	Semi standard non polar	33892256
Procurcumenol,1TBDMS,isomer #1	CC1=CC(=O)C(=C(C)C)CC2C1CCC2(C)O[Si](C)(C)C(C)(C)C	2208.2	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 - Procurcumenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-066u-3950000000-993f8de2081ec44fe521	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Procurcumenol GC-MS (1 TMS) - 70eV, Positive	splash10-03dr-4690000000-50dff9364ebbe493c97e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Procurcumenol 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 - Procurcumenol 10V, Positive-QTOF	splash10-014r-0190000000-83ff7bf49115c97d99a5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 20V, Positive-QTOF	splash10-014r-2970000000-40fd2709b561d8e607f2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 40V, Positive-QTOF	splash10-0gb9-9620000000-80e096a7985ac6ddecf2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 10V, Negative-QTOF	splash10-001i-0090000000-6f7e6bc4fca4d9030843	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 20V, Negative-QTOF	splash10-001i-0190000000-14de31412f9f14f1d1b7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 40V, Negative-QTOF	splash10-000i-6940000000-45e1f7a1d3feb95a9670	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 20V, Negative-QTOF	splash10-001i-0190000000-8762faa7c896b602e28b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 40V, Negative-QTOF	splash10-014i-6930000000-7563fe81c0d128bcbf78	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 10V, Positive-QTOF	splash10-00kr-0190000000-189a46161700f2a6f32a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 20V, Positive-QTOF	splash10-014i-3980000000-2bcf5d27f6a4299b43fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procurcumenol 40V, Positive-QTOF	splash10-00nf-9210000000-bfcfb2c36e80c1528b45	2021-09-22	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

FDB015314

KNApSAcK ID

C00020416

Chemspider ID

4478722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320710

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021981

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 Procurcumenol (HMDB0036427)

MOL for HMDB0036427 (Procurcumenol)

3D MOL for HMDB0036427 (Procurcumenol)

3D SDF for HMDB0036427 (Procurcumenol)

3D-SDF for HMDB0036427 (Procurcumenol)

PDB for HMDB0036427 (Procurcumenol)

3D PDB for HMDB0036427 (Procurcumenol)

SMILES for HMDB0036427 (Procurcumenol)

INCHI for HMDB0036427 (Procurcumenol)

Structure for HMDB0036427 (Procurcumenol)

3D Structure for HMDB0036427 (Procurcumenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra