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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:24:23 UTC

Update Date

2022-09-22 18:34:26 UTC

HMDB ID

HMDB0038122

Secondary Accession Numbers

HMDB38122

Metabolite Identification

Common Name

Curcumol

Description

5-Methyl-5-hexen-2-one, also known as 4-acetyl-2-methyl-1-butene or fema 3365, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 5-Methyl-5-hexen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methyl-5-hexen-2-one is a foliage, green, and vegetable tasting compound. Outside of the human body,.

Structure

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

HMDB0038122
     RDKit          3D
Curcumol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.0940    2.7624   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515    1.7850   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.0870    0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    0.7967    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6269    1.0803    1.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -0.0811    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -0.6284   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -0.9981   -0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    0.2099   -0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027   -0.1600   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    1.0109   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0337   -1.2536    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6528   -1.8064    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -2.0912    1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401   -1.4923   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9990    0.0217   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704    0.4019   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    2.5744   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    3.7991   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592    2.7984    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    2.5656   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.0477    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2699   -1.0985   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -1.9214   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.8746   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502   -0.5474   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012    1.0745    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338    0.9649   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    1.9306   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952   -2.2701    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796   -1.0537    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -1.2824    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.7043   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0662   -2.2588    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.0719    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -1.3567    2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637   -1.6802   -1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8115   -1.9979   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591    0.2610    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    0.4885   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    0.2196   -1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061310142D          

 17 19  0  0  0  0            999 V2000
    4.9456   -0.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4747    0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    2.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889   -1.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007    0.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4643    1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159    1.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    0.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6251    1.3913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194    0.7541    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  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038122

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CC23OC1(O)CC(=C)C2CCC3C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3

> <INCHI_KEY>
QRMPRVXWPCLVNI-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.58681616412169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.072763619

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.751473591769766

> <JCHEM_PKA_STRONGEST_BASIC>
-4.219705450959904

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
67.9193

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-isopropyl-2-methyl-6-methylidene-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038122
     RDKit          3D
Curcumol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.0940    2.7624   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515    1.7850   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.0870    0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    0.7967    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6269    1.0803    1.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -0.0811    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -0.6284   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -0.9981   -0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    0.2099   -0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027   -0.1600   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    1.0109   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0337   -1.2536    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6528   -1.8064    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -2.0912    1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401   -1.4923   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9990    0.0217   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704    0.4019   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    2.5744   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    3.7991   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592    2.7984    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    2.5656   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.0477    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2699   -1.0985   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -1.9214   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.8746   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502   -0.5474   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012    1.0745    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338    0.9649   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    1.9306   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952   -2.2701    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796   -1.0537    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -1.2824    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.7043   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0662   -2.2588    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.0719    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -1.3567    2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637   -1.6802   -1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8115   -1.9979   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591    0.2610    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    0.4885   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    0.2196   -1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  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       9.232  -1.563   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.219   0.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.131   4.823   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.086  -1.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.435   0.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.615   1.741   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.467   3.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.239  -0.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.022  -0.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.883   3.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.825  -0.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.116   2.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.616   0.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.931   0.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.220   2.044   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.634   2.597   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.009   1.408   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7   10   15                                                       
CONECT    8   13   14                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    7   12                                                  
CONECT   11    4    5   14                                                  
CONECT   12    6   10   14                                                  
CONECT   13    8    9   15                                                  
CONECT   14    8   11   12   17                                             
CONECT   15    7   13   16   17                                             
CONECT   16   15                                                            
CONECT   17   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0038122
HETATM    1  C1  UNL     1      -2.094   2.762  -0.712  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.251   1.785  -0.463  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.029   2.087   0.209  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.738   0.797   0.640  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.627   1.080   1.647  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.247  -0.081   1.073  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.771  -0.628  -0.077  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.504  -0.998  -0.847  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.357   0.210  -0.585  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.803  -0.160  -0.422  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.650   1.011  -0.071  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.034  -1.254   0.579  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.653  -1.806   0.154  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.957  -2.091   1.586  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.940  -1.492  -0.620  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.999   0.022  -0.449  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.570   0.402  -0.845  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.057   2.574  -1.212  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.910   3.799  -0.453  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.059   2.798   1.042  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.719   2.566  -0.538  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.571   2.048   1.897  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.270  -1.099  -1.926  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.871  -1.921  -0.401  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.284   0.875  -1.471  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.150  -0.547  -1.411  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.901   1.074   1.017  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.634   0.965  -0.598  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.153   1.931  -0.440  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.795  -2.270   0.181  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.580  -1.054   1.561  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.146  -1.282   0.764  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.221  -2.704  -0.360  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.066  -2.259   1.676  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.476  -3.072   1.860  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.576  -1.357   2.301  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.764  -1.680  -1.684  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.812  -1.998  -0.193  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.159   0.261   0.636  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.746   0.489  -1.105  1.00  0.00           H  
HETATM   41  H24 UNL     1      -1.486   0.220  -1.938  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4   20   21
CONECT    4    5    6    9
CONECT    5   22
CONECT    6    7
CONECT    7    8   13   17
CONECT    8    9   23   24
CONECT    9   10   25
CONECT   10   11   12   26
CONECT   11   27   28   29
CONECT   12   30   31   32
CONECT   13   14   15   33
CONECT   14   34   35   36
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   41
END

HMDB0038122
     RDKit          3D
Curcumol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.0940    2.7624   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515    1.7850   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.0870    0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    0.7967    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6269    1.0803    1.6465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -0.0811    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -0.6284   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -0.9981   -0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    0.2099   -0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027   -0.1600   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    1.0109   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0337   -1.2536    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6528   -1.8064    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -2.0912    1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401   -1.4923   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9990    0.0217   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704    0.4019   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    2.5744   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    3.7991   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592    2.7984    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    2.5656   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.0477    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2699   -1.0985   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -1.9214   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.8746   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502   -0.5474   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012    1.0745    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338    0.9649   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    1.9306   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952   -2.2701    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796   -1.0537    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -1.2824    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.7043   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0662   -2.2588    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.0719    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -1.3567    2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637   -1.6802   -1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8115   -1.9979   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591    0.2610    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    0.4885   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    0.2196   -1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Acetyl-2-methyl-1-butene	HMDB
FEMA 3365	HMDB
Methallylacetone	HMDB
5,8-Epoxy-10(14)-guaien-8-ol	HMDB
Curcumol	MeSH

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

Traditional Name

9-isopropyl-2-methyl-6-methylidene-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

CAS Registry Number

4871-97-0

SMILES

CC(C)C1CC23OC1(O)CC(=C)C2CCC3C

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3

InChI Key

QRMPRVXWPCLVNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038122)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038122)

Source

Endogenous

Endogenous (HMDB: HMDB0038122)

Plant

Plant (HMDB: HMDB0038122)

Animal

Animal (HMDB: HMDB0038122)

Exogenous

Food

Food (HMDB: HMDB0038122)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038122)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038122)

Cellular process

Cell signaling (HMDB: HMDB0038122)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038122)

Role

Biological role

Nutrient

Nutrient (HMDB: HMDB0038122)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038122)

Emulsifier (HMDB: HMDB0038122)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.63	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.92 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	3	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]+	153.21	31661259
DarkChem	[M-H]-	150.471	31661259
DeepCCS	[M-2H]-	190.947	30932474
DeepCCS	[M+Na]+	166.075	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.5	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	163.2	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcumol	CC(C)C1CC23OC1(O)CC(=C)C2CCC3C	2259.7	Standard polar	33892256
Curcumol	CC(C)C1CC23OC1(O)CC(=C)C2CCC3C	1650.6	Standard non polar	33892256
Curcumol	CC(C)C1CC23OC1(O)CC(=C)C2CCC3C	1713.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcumol,1TMS,isomer #1	C=C1CC2(O[Si](C)(C)C)OC3(CC2C(C)C)C(C)CCC13	1730.0	Semi standard non polar	33892256
Curcumol,1TBDMS,isomer #1	C=C1CC2(O[Si](C)(C)C(C)(C)C)OC3(CC2C(C)C)C(C)CCC13	1996.0	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 - Curcumol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9430000000-e1674cb346da569a2fb6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumol GC-MS (1 TMS) - 70eV, Positive	splash10-000l-9030000000-399b7159ca48b41b17f7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumol 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 - Curcumol 10V, Positive-QTOF	splash10-000i-2090000000-873dc9ce8ca841c2c385	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 20V, Positive-QTOF	splash10-05n0-9250000000-2aec5e80266e381c8d6f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 40V, Positive-QTOF	splash10-0a4i-9000000000-077b489b17b45ea88ce3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 10V, Negative-QTOF	splash10-000i-0090000000-d47490971e8b0274931d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 20V, Negative-QTOF	splash10-000i-0290000000-80d9c57bbfa557fabffe	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 40V, Negative-QTOF	splash10-066r-6910000000-3ba867119318826e533b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 20V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 40V, Negative-QTOF	splash10-00kr-0690000000-06dfb3057102cc0a9617	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 10V, Positive-QTOF	splash10-000i-0090000000-8472a524647920e2eae7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 20V, Positive-QTOF	splash10-000i-0090000000-a35b1ee8d04c47073402	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumol 40V, Positive-QTOF	splash10-0a4s-7950000000-d30c841ef7a06a60bed9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB008163

KNApSAcK ID

Not Available

Chemspider ID

198976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

228604

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhang W, Wang Z, Chen T: Curcumol induces apoptosis via caspases-independent mitochondrial pathway in human lung adenocarcinoma ASTC-a-1 cells. Med Oncol. 2011 Mar;28(1):307-14. doi: 10.1007/s12032-010-9431-5. Epub 2010 Feb 3. [PubMed:20127426 ]
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 Curcumol (HMDB0038122)

MOL for HMDB0038122 (Curcumol)

3D MOL for HMDB0038122 (Curcumol)

3D SDF for HMDB0038122 (Curcumol)

3D-SDF for HMDB0038122 (Curcumol)

PDB for HMDB0038122 (Curcumol)

3D PDB for HMDB0038122 (Curcumol)

SMILES for HMDB0038122 (Curcumol)

INCHI for HMDB0038122 (Curcumol)

Structure for HMDB0038122 (Curcumol)

3D Structure for HMDB0038122 (Curcumol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra