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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002114

Secondary Accession Numbers

HMDB02114

Metabolite Identification

Common Name

Bisdemethoxycurcumin

Description

Bisdemethoxycurcumin is a curcuminoid, a component of tumeric. Tumeric is a spice that comes from the root Curcuma longa, a member of the ginger family, Zingaberaceae. It is bright yellow and has been used as a coloring agent in food in the United States. In India, it has been used for centuries as a spice and a food preservative, and also for its various medicinal properties. In Ayurveda (Indian traditional medicine), tumeric has been used for its medicinal properties for various indications and through different routes of administration. It has been used topically on the skin for wounds, blistering diseases such as pemphigus and herpes zoster, for parasitic skin infections, and for acne. It has been used via oral administration for the common cold, liver diseases, urinary tract diseases, and as a blood purifier. For chronic rhinitis and coryza, it has been used via inhalation. The average intake of tumeric in the diet in India is approximately 2 to 2.5 g in a 60 kg individual. This corresponds to an intake of approximately 60 to 100 mg of curcumin daily. The Food and Drug Administration has classified tumeric among substances Generally Recognized as Safe (GRAS). A large number of in vitro and animal studies have been conducted to evaluate the effect of curcumin on inflammation. It has been found to act at various different levels of the arachadonic acid inflammatory cascade and through effects on various enzymes and cytokines. (PMID: 12676044 ).

Structure

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

HMDB0002114
     RDKit          3D
Bisdemethoxycurcumin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.1913   -0.3640   -2.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -0.2059   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -0.1348   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121   -0.2316   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7437   -0.1723   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9493   -0.2894   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1594   -0.2375   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1810   -0.0666    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3629   -0.0111    1.6564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    0.0533    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8234   -0.0039    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.0921   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -0.1924   -1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -0.3499   -3.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -0.1099   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.0563   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.1453    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8243    0.3205    1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1325    0.4111    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1527    0.3246    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4636    0.4187    1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8608    0.1503   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    0.0619   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2026    0.0013    0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.3691   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.4236   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0959   -0.3310   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7389   -0.8773    2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9920    0.1903    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    0.0911    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.8664   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.8844   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.1854   -2.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.1333    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.3946    2.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    0.5500    2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9257    1.3168    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6688    0.0842   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973   -0.0739   -1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 11  5  1  0
 23 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

Bismethoxycurcumin
  Mrv1652309241723512D          

 23 24  0  0  0  0            999 V2000
    4.6326    1.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036    1.8001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9195   -0.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -0.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7761    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036    0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7761   -0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601   -0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906   -0.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2051    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -0.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2051   -0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2  9  2  0  0  0  0
  3 23  1  0  0  0  0
  4 22  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 15  2  0  0  0  0
  6 17  1  0  0  0  0
  7 11  1  0  0  0  0
  7 14  2  0  0  0  0
  7 16  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 21  2  0  0  0  0
 18 23  2  0  0  0  0
 19 22  2  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002114

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

> <INCHI_KEY>
PREBVFJICNPEKM-YDWXAUTNSA-N

> <FORMULA>
C19H16O4

> <MOLECULAR_WEIGHT>
308.3279

> <EXACT_MASS>
308.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.577304366876206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
4.439867082333333

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.241861075434462

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.690004821553735

> <JCHEM_PKA_STRONGEST_BASIC>
-4.648276198332676

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
90.88420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisdemethoxycurcumin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002114
     RDKit          3D
Bisdemethoxycurcumin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.1913   -0.3640   -2.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -0.2059   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -0.1348   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121   -0.2316   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7437   -0.1723   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9493   -0.2894   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1594   -0.2375   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1810   -0.0666    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3629   -0.0111    1.6564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    0.0533    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8234   -0.0039    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.0921   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -0.1924   -1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -0.3499   -3.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -0.1099   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.0563   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.1453    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8243    0.3205    1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1325    0.4111    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1527    0.3246    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4636    0.4187    1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8608    0.1503   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    0.0619   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2026    0.0013    0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.3691   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.4236   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0959   -0.3310   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7389   -0.8773    2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9920    0.1903    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    0.0911    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.8664   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.8844   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.1854   -2.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.1333    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.3946    2.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    0.5500    2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9257    1.3168    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6688    0.0842   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973   -0.0739   -1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 11  5  1  0
 23 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 24-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Bismethoxycurcumin                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-17         0                                  
HETATM    1  O   UNK     0       8.648   3.360   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.980   3.360   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.650  -1.260   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.022  -1.260   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.314   1.050   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.979   1.050   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.649   1.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.648   1.820   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.980   1.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.313   1.820   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.315   1.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.646   1.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.981   1.050   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.649  -0.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.645   1.820   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.982   1.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.979  -0.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.982  -1.260   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.688   1.050   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.316   1.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.645  -1.259   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.688  -0.490   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.316  -0.490   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   23                                                            
CONECT    4   22                                                            
CONECT    5    8    9                                                       
CONECT    6   10   15   17                                                  
CONECT    7   11   14   16                                                  
CONECT    8    1    5   13                                                  
CONECT    9    2    5   12                                                  
CONECT   10    6   12                                                       
CONECT   11    7   13                                                       
CONECT   12    9   10                                                       
CONECT   13    8   11                                                       
CONECT   14    7   18                                                       
CONECT   15    6   19                                                       
CONECT   16    7   20                                                       
CONECT   17    6   21                                                       
CONECT   18   14   23                                                       
CONECT   19   15   22                                                       
CONECT   20   16   23                                                       
CONECT   21   17   22                                                       
CONECT   22    4   19   21                                                  
CONECT   23    3   18   20                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0002114
HETATM    1  O1  UNL     1      -1.191  -0.364  -2.739  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.087  -0.206  -1.499  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.303  -0.135  -0.664  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.512  -0.232  -1.171  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.744  -0.172  -0.426  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.949  -0.289  -1.097  1.00  0.00           C  
HETATM    7  C6  UNL     1      -7.159  -0.237  -0.416  1.00  0.00           C  
HETATM    8  C7  UNL     1      -7.181  -0.067   0.953  1.00  0.00           C  
HETATM    9  O2  UNL     1      -8.363  -0.011   1.656  1.00  0.00           O  
HETATM   10  C8  UNL     1      -6.000   0.053   1.651  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.823  -0.004   0.935  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.233  -0.092  -0.881  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.279  -0.192  -1.912  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.965  -0.350  -3.101  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.716  -0.110  -1.571  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.113   0.056  -0.331  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.491   0.145   0.076  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.824   0.320   1.401  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.132   0.411   1.836  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.153   0.325   0.920  1.00  0.00           C  
HETATM   21  O4  UNL     1       8.464   0.419   1.382  1.00  0.00           O  
HETATM   22  C18 UNL     1       6.861   0.150  -0.407  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.529   0.062  -0.819  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.203   0.001   0.401  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.534  -0.369  -2.264  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.925  -0.424  -2.174  1.00  0.00           H  
HETATM   27  H4  UNL     1      -8.096  -0.331  -0.957  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.739  -0.877   2.005  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.992   0.190   2.743  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.908   0.091   1.493  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.332  -0.866  -0.090  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.362   0.884  -0.329  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.470  -0.185  -2.340  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.346   0.133   0.453  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.059   0.395   2.162  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.388   0.550   2.889  1.00  0.00           H  
HETATM   37  H14 UNL     1       8.926   1.317   1.445  1.00  0.00           H  
HETATM   38  H15 UNL     1       7.669   0.084  -1.114  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.397  -0.074  -1.875  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   11
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13   31   32
CONECT   13   14   14   15
CONECT   15   16   16   33
CONECT   16   17   34
CONECT   17   18   18   23
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   21   22
CONECT   21   37
CONECT   22   23   23   38
CONECT   23   39
END

HMDB0002114
     RDKit          3D
Bisdemethoxycurcumin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.1913   -0.3640   -2.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871   -0.2059   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -0.1348   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121   -0.2316   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7437   -0.1723   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9493   -0.2894   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1594   -0.2375   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1810   -0.0666    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3629   -0.0111    1.6564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    0.0533    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8234   -0.0039    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.0921   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -0.1924   -1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -0.3499   -3.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -0.1099   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.0563   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.1453    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8243    0.3205    1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1325    0.4111    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1527    0.3246    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4636    0.4187    1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8608    0.1503   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293    0.0619   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2026    0.0013    0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345   -0.3691   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.4236   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0959   -0.3310   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7389   -0.8773    2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9920    0.1903    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    0.0911    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.8664   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.8844   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -0.1854   -2.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.1333    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.3946    2.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    0.5500    2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9257    1.3168    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6688    0.0842   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973   -0.0739   -1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 11  5  1  0
 23 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione	ChEBI
Bis(4-hydroxycinnamoyl)methane	ChEBI
Bis(p-hydroxycinnamoyl)methane	ChEBI
Curcumin III	ChEBI
Didemethoxycurcumin	ChEBI
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)	HMDB
Bis-demethoxycurcumin	HMDB

Chemical Formula

C₁₉H₁₆O₄

Average Molecular Weight

308.3279

Monoisotopic Molecular Weight

308.104859

IUPAC Name

(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

Traditional Name

bisdemethoxycurcumin

CAS Registry Number

24939-16-0

SMILES

OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

InChI Key

PREBVFJICNPEKM-YDWXAUTNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Hydroxycinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1,3-diketone
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enone (CHEBI:71045 )
polyphenol (CHEBI:71045 )
beta-diketone (CHEBI:71045 )
diarylheptanoid (CHEBI:71045 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0002114)

Turmeric (FooDB: FOOD00068)

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Biological role

anti aflatoxin (HMDB: HMDB0002114)
anti Alzheimeran (HMDB: HMDB0002114)
anti amyloid-beta (HMDB: HMDB0002114)
antiangiogenic (HMDB: HMDB0002114)
anti choleretic (HMDB: HMDB0002114)
anti inflammatory (HMDB: HMDB0002114)
anti leishmanic (HMDB: HMDB0002114)
anti lipoperoxidant (HMDB: HMDB0002114)
anti mutagenic (HMDB: HMDB0002114)
anti nitrosating (HMDB: HMDB0002114)
Antioxidant (HMDB: HMDB0002114)
anti papillomic (HMDB: HMDB0002114)
antitumor promoter (HMDB: HMDB0002114)
DNA-protective (HMDB: HMDB0002114)
nitric-oxide scavenger (HMDB: HMDB0002114)
plasmodicide (HMDB: HMDB0002114)
quinone-reductase inducer (HMDB: HMDB0002114)

Modulator

Inhibitor

Enzyme inhibitor

angiogenesis inhibitor (HMDB: HMDB0002114)
sortase-A inhibitor (HMDB: HMDB0002114)
topoisomerase-II inhibitor (HMDB: HMDB0002114)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0002114)

Indirect biological role

antioxidant (HMDB: HMDB0002114)

Industrial application

Agriculture

Pesticide

Insecticide

nematicide (HMDB: HMDB0002114)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	551.00 to 552.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	32.69 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.155 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.46	ALOGPS
logP	4.44	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.88 m³·mol⁻¹	ChemAxon
Polarizability	32.58 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
DeepCCS	[M+H]+	178.186	30932474
DeepCCS	[M-H]-	175.828	30932474
DeepCCS	[M-2H]-	209.831	30932474
DeepCCS	[M+Na]+	185.059	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.6	32859911
AllCCS	[M-H]-	173.4	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	173.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisdemethoxycurcumin	OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	5467.7	Standard polar	33892256
Bisdemethoxycurcumin	OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	2966.7	Standard non polar	33892256
Bisdemethoxycurcumin	OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	3544.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisdemethoxycurcumin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)C=C1	3185.9	Semi standard non polar	33892256
Bisdemethoxycurcumin,1TMS,isomer #2	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O)C=C1)/C=C/C1=CC=C(O)C=C1	3402.1	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C=C1	3212.1	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TMS,isomer #2	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3497.3	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)/C=C/C1=CC=C(O)C=C1	3498.7	Semi standard non polar	33892256
Bisdemethoxycurcumin,3TMS,isomer #1	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3485.6	Semi standard non polar	33892256
Bisdemethoxycurcumin,3TMS,isomer #1	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3470.9	Standard non polar	33892256
Bisdemethoxycurcumin,3TMS,isomer #1	C[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3472.3	Standard polar	33892256
Bisdemethoxycurcumin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)C=C1	3451.8	Semi standard non polar	33892256
Bisdemethoxycurcumin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O)C=C1)/C=C/C1=CC=C(O)C=C1	3698.5	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1	3807.1	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4016.6	Semi standard non polar	33892256
Bisdemethoxycurcumin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)/C=C/C1=CC=C(O)C=C1	4018.6	Semi standard non polar	33892256
Bisdemethoxycurcumin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4289.5	Semi standard non polar	33892256
Bisdemethoxycurcumin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4100.8	Standard non polar	33892256
Bisdemethoxycurcumin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3665.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdemethoxycurcumin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0900000000-80dee0b7da47096385f3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdemethoxycurcumin GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-4693400000-4dfcfa07fb4fcf08d15a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdemethoxycurcumin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisdemethoxycurcumin LC-ESI-ITTOF , negative-QTOF	splash10-000f-0900000000-b6262ce6a5bc848338cc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 10V, Positive-QTOF	splash10-0a4i-0319000000-51bdfbd78f352db8c233	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 20V, Positive-QTOF	splash10-0a4j-0911000000-feb1ff110feb9ee4d644	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 40V, Positive-QTOF	splash10-0690-3900000000-80607bb0dba3055c2ec4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 10V, Negative-QTOF	splash10-0a4i-0109000000-d6136d3ecd9a3055073b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 20V, Negative-QTOF	splash10-0a4i-0918000000-8da010127482f9dbe837	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 40V, Negative-QTOF	splash10-07vl-1910000000-7b9ad6f38949b0ffed21	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 10V, Negative-QTOF	splash10-0ap0-0907000000-a0e824005455e435a22b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 20V, Negative-QTOF	splash10-066r-0924000000-b8be7e1dc7f7aebc8446	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 40V, Negative-QTOF	splash10-014i-0920000000-3f12cad48a69d6a54824	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 10V, Positive-QTOF	splash10-0a4i-0309000000-59ab1e9ec81516f1adcb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 20V, Positive-QTOF	splash10-0002-0900000000-b4cdb8c134bf3a01b5cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdemethoxycurcumin 40V, Positive-QTOF	splash10-014i-0910000000-297489cfaed0405d2f7a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

CPD-12188

BiGG ID

Not Available

Wikipedia Link

Bisdemethoxycurcumin

METLIN ID

Not Available

PubChem Compound

5315472

PDB ID

Not Available

ChEBI ID

71045

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1436991

References

Synthesis Reference

Park So-Young; Kim Darrick S H L Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease. Journal of natural products (2002), 65(9), 1227-31.

Material Safety Data Sheet (MSDS)

Not Available

General References

Chainani-Wu N: Safety and anti-inflammatory activity of curcumin: a component of tumeric (Curcuma longa). J Altern Complement Med. 2003 Feb;9(1):161-8. [PubMed:12676044 ]

Showing metabocard for Bisdemethoxycurcumin (HMDB0002114)

MOL for HMDB0002114 (Bisdemethoxycurcumin)

3D MOL for HMDB0002114 (Bisdemethoxycurcumin)

3D SDF for HMDB0002114 (Bisdemethoxycurcumin)

3D-SDF for HMDB0002114 (Bisdemethoxycurcumin)

PDB for HMDB0002114 (Bisdemethoxycurcumin)

3D PDB for HMDB0002114 (Bisdemethoxycurcumin)

SMILES for HMDB0002114 (Bisdemethoxycurcumin)

INCHI for HMDB0002114 (Bisdemethoxycurcumin)

Structure for HMDB0002114 (Bisdemethoxycurcumin)

3D Structure for HMDB0002114 (Bisdemethoxycurcumin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra