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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:25:08 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038136

Secondary Accession Numbers

HMDB38136

Metabolite Identification

Common Name

Curcumadiol

Description

Curcumadiol 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 small amount of articles have been published on Curcumadiol.

Structure

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

HMDB0038136
     RDKit          3D
Curcumadiol
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.2284   -1.4923    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -0.2247   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -0.4307   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345    0.2940   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    1.4611    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234    2.3390    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924    1.8948    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.2227   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746    2.7606    1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5383    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.3472    1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -1.1477    0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -1.3929   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.8602   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.8925   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -0.6396    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651   -0.5367   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752   -2.3174   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298   -1.7680    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165   -1.3300    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.5418   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.5125   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    0.4628   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.3788   -2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.8814    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4529    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    3.3585    0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0185   -1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3019    3.3506   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    1.8374   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246    3.6724    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.5654    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    0.5537    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    0.9230    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.7097    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -1.3157    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -3.2702   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -3.0780   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -3.4329    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435   -0.4701   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -1.3675    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.5850   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3229   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 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
 17  4  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
M  END


  Mrv0541 05061310152D          

 17 18  0  0  0  0            999 V2000
    4.3699   -1.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -0.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    2.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -0.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -0.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    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
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    2.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085   -0.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  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  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038136

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CCC(C)(O)C2CCC(C)(O)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3,16)12-6-8-15(4,17)13(12)9-11/h5,10,12-13,16-17H,6-9H2,1-4H3

> <INCHI_KEY>
FNMDHMSGEIODFP-UHFFFAOYSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.3657

> <EXACT_MASS>
238.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.36197920315869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulene-1,4-diol

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.2235127289999994

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.04596435866846

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.43582605228179

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9012435872672615

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
71.1126

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-isopropyl-1,4-dimethyl-2,3,3a,5,8,8a-hexahydroazulene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038136
     RDKit          3D
Curcumadiol
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.2284   -1.4923    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -0.2247   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -0.4307   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345    0.2940   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    1.4611    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234    2.3390    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924    1.8948    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.2227   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746    2.7606    1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5383    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.3472    1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -1.1477    0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -1.3929   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.8602   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.8925   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -0.6396    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651   -0.5367   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752   -2.3174   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298   -1.7680    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165   -1.3300    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.5418   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.5125   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    0.4628   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.3788   -2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.8814    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4529    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    3.3585    0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0185   -1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3019    3.3506   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    1.8374   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246    3.6724    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.5654    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    0.5537    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    0.9230    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.7097    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -1.3157    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -3.2702   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -3.0780   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -3.4329    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435   -0.4701   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -1.3675    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.5850   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3229   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 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
 17  4  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  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       8.157  -2.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.243  -0.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.054   4.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.216  -0.729   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.720  -0.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.054   2.694   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       6.258   3.654   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.926   5.041   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.256  -0.092   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   14                                                       
CONECT    8    6   15                                                       
CONECT    9   11   13                                                       
CONECT   10    1    2   11                                                  
CONECT   11    5    9   10                                                  
CONECT   12    6   13   14                                                  
CONECT   13    9   12   15                                                  
CONECT   14    3    7   12   16                                             
CONECT   15    4    8   13   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0038136
HETATM    1  C1  UNL     1       3.228  -1.492   0.147  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.998  -0.225  -0.607  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.092  -0.431  -2.100  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.635   0.294  -0.219  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.654   1.461   0.382  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.623   2.339   0.926  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.792   1.895   0.638  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.187   2.223  -0.749  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.575   2.761   1.459  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.086   0.538   1.152  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.598   0.347   1.241  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.811  -1.148   0.971  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.768  -1.393  -0.093  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.472  -2.860  -0.270  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.161  -0.893  -1.310  1.00  0.00           O  
HETATM   16  C14 UNL     1      -0.578  -0.640   0.501  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.465  -0.537  -0.548  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.475  -2.317  -0.578  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.330  -1.768   0.723  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.116  -1.330   0.824  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.768   0.542  -0.364  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.179  -0.513  -2.337  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.720   0.463  -2.602  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.633  -1.379  -2.437  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.664   1.881   0.511  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.693   2.453   2.049  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.783   3.359   0.527  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.416   2.019  -1.516  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.302   3.351  -0.798  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.181   1.837  -1.023  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.225   3.672   1.275  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.755   0.565   2.238  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.004   0.554   2.232  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.157   0.923   0.509  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.557  -1.710   1.879  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.837  -1.316   0.602  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.250  -3.270  -0.950  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.504  -3.078  -0.714  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.544  -3.433   0.676  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.044  -0.470  -1.250  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.183  -1.368   1.277  1.00  0.00           H  
HETATM   42  H25 UNL     1       0.879  -1.585  -0.696  1.00  0.00           H  
HETATM   43  H26 UNL     1       0.049  -0.323  -1.579  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5    5   17
CONECT    5    6   25
CONECT    6    7   26   27
CONECT    7    8    9   10
CONECT    8   28   29   30
CONECT    9   31
CONECT   10   11   16   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   15   16
CONECT   14   37   38   39
CONECT   15   40
CONECT   16   17   41
CONECT   17   42   43
END

HMDB0038136
     RDKit          3D
Curcumadiol
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.2284   -1.4923    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -0.2247   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -0.4307   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345    0.2940   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    1.4611    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234    2.3390    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924    1.8948    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.2227   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746    2.7606    1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5383    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.3472    1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -1.1477    0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -1.3929   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.8602   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.8925   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -0.6396    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651   -0.5367   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752   -2.3174   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298   -1.7680    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165   -1.3300    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.5418   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791   -0.5125   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    0.4628   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.3788   -2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.8814    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4529    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    3.3585    0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0185   -1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3019    3.3506   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1808    1.8374   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246    3.6724    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.5654    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    0.5537    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    0.9230    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.7097    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -1.3157    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -3.2702   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -3.0780   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -3.4329    0.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435   -0.4701   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -1.3675    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.5850   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3229   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 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
 17  4  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cucumadiol	HMDB

Chemical Formula

C₁₅H₂₆O₂

Average Molecular Weight

238.3657

Monoisotopic Molecular Weight

238.193280076

IUPAC Name

1,4-dimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulene-1,4-diol

Traditional Name

7-isopropyl-1,4-dimethyl-2,3,3a,5,8,8a-hexahydroazulene-1,4-diol

CAS Registry Number

31946-48-2

SMILES

CC(C)C1=CCC(C)(O)C2CCC(C)(O)C2C1

InChI Identifier

InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3,16)12-6-8-15(4,17)13(12)9-11/h5,10,12-13,16-17H,6-9H2,1-4H3

InChI Key

FNMDHMSGEIODFP-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
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038136)

Source

Endogenous

Endogenous (HMDB: HMDB0038136)

Animal

Animal (HMDB: HMDB0038136)

Exogenous

Food

Food (HMDB: HMDB0038136)

Exogenous (HMDB: HMDB0038136)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038136)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038136)

Lipid metabolism pathway (HMDB: HMDB0038136)

Cellular process

Cell signaling (HMDB: HMDB0038136)

Biochemical process

Lipid transport (HMDB: HMDB0038136)

Role

Biological role

Energy source (HMDB: HMDB0038136)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038136)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 - 145.5 °C	Not Available
Boiling Point	342.00 to 344.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	19.96 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.027 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.22	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.11 m³·mol⁻¹	ChemAxon
Polarizability	28.36 Å³	ChemAxon
Number of Rings	2	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]+	157.163	31661259
DarkChem	[M-H]-	154.215	31661259
DeepCCS	[M+H]+	163.018	30932474
DeepCCS	[M-H]-	160.66	30932474
DeepCCS	[M-2H]-	193.552	30932474
DeepCCS	[M+Na]+	169.111	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	164.5	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.	4.26 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4133 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.86 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2169.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	636.3 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	639.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	949.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	392.9 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	1112.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	299.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	457.5 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	16.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcumadiol	CC(C)C1=CCC(C)(O)C2CCC(C)(O)C2C1	2573.3	Standard polar	33892256
Curcumadiol	CC(C)C1=CCC(C)(O)C2CCC(C)(O)C2C1	1724.8	Standard non polar	33892256
Curcumadiol	CC(C)C1=CCC(C)(O)C2CCC(C)(O)C2C1	1762.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcumadiol,1TMS,isomer #1	CC(C)C1=CCC(C)(O[Si](C)(C)C)C2CCC(C)(O)C2C1	1894.2	Semi standard non polar	33892256
Curcumadiol,1TMS,isomer #2	CC(C)C1=CCC(C)(O)C2CCC(C)(O[Si](C)(C)C)C2C1	1904.2	Semi standard non polar	33892256
Curcumadiol,2TMS,isomer #1	CC(C)C1=CCC(C)(O[Si](C)(C)C)C2CCC(C)(O[Si](C)(C)C)C2C1	1936.1	Semi standard non polar	33892256
Curcumadiol,1TBDMS,isomer #1	CC(C)C1=CCC(C)(O[Si](C)(C)C(C)(C)C)C2CCC(C)(O)C2C1	2113.3	Semi standard non polar	33892256
Curcumadiol,1TBDMS,isomer #2	CC(C)C1=CCC(C)(O)C2CCC(C)(O[Si](C)(C)C(C)(C)C)C2C1	2128.4	Semi standard non polar	33892256
Curcumadiol,2TBDMS,isomer #1	CC(C)C1=CCC(C)(O[Si](C)(C)C(C)(C)C)C2CCC(C)(O[Si](C)(C)C(C)(C)C)C2C1	2386.8	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 - Curcumadiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-2940000000-0601b37a816b52bd975d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumadiol GC-MS (2 TMS) - 70eV, Positive	splash10-014i-5198000000-2fa0824bd0c289cfd63c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumadiol 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 - Curcumadiol 10V, Positive-QTOF	splash10-00dr-0090000000-d25ad02da5d5d7849600	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 20V, Positive-QTOF	splash10-0fk9-1490000000-94b39166ca56b1d2744e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 40V, Positive-QTOF	splash10-0zfr-9540000000-555464f02fa9ecfc9414	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 10V, Negative-QTOF	splash10-000i-0090000000-c22709265fa653a57003	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 20V, Negative-QTOF	splash10-00kr-0090000000-faa4766d662593e01cc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 40V, Negative-QTOF	splash10-002e-5930000000-6af4294a8e156e739ea6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 10V, Negative-QTOF	splash10-000i-0090000000-e665f494a7390ebf108d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 20V, Negative-QTOF	splash10-000i-0090000000-e665f494a7390ebf108d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 40V, Negative-QTOF	splash10-00kr-0090000000-f3d100112e440072575a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 10V, Positive-QTOF	splash10-00dr-0190000000-461f2536f23944e1ba79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 20V, Positive-QTOF	splash10-00ai-7960000000-78cedc4e1aeab93609d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumadiol 40V, Positive-QTOF	splash10-001i-9210000000-1c5beacf2374d2200a65	2021-09-24	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

FDB017364

KNApSAcK ID

C00020412

Chemspider ID

4475313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316212

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1615941

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 Curcumadiol (HMDB0038136)

MOL for HMDB0038136 (Curcumadiol)

3D MOL for HMDB0038136 (Curcumadiol)

3D SDF for HMDB0038136 (Curcumadiol)

3D-SDF for HMDB0038136 (Curcumadiol)

PDB for HMDB0038136 (Curcumadiol)

3D PDB for HMDB0038136 (Curcumadiol)

SMILES for HMDB0038136 (Curcumadiol)

INCHI for HMDB0038136 (Curcumadiol)

Structure for HMDB0038136 (Curcumadiol)

3D Structure for HMDB0038136 (Curcumadiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra