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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:33:54 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033801

Secondary Accession Numbers

HMDB33801

Metabolite Identification

Common Name

Demethoxycurcumin

Description

Demethoxycurcumin, also known as curcuminii or BHCFM, 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. Demethoxycurcumin is found, on average, in the highest concentration within turmerics (Curcuma longa). Demethoxycurcumin has also been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and root vegetables. This could make demethoxycurcumin a potential biomarker for the consumption of these foods. Demethoxycurcumin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Demethoxycurcumin.

Structure

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

HMDB0033801
     RDKit          3D
Demethoxycurcumin
 43 44  0  0  0  0  0  0  0  0999 V2000
   -6.4414    0.3018    2.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8632    0.3625    0.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9709    0.3940   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131    0.3297   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    0.3569   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2505    0.2470   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949    0.0909    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.0221    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.1773    1.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984    0.0358   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -1.1731   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -2.2717   -0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9336   -1.2023   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -0.1328    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -0.2338    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    0.9276    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0541    0.9056    1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -0.3198    1.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0436   -0.3454    1.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0510   -1.4847    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -1.4304    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817    0.4541   -2.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5218    0.5218   -2.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4268    0.4908   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7795    0.5517   -1.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0492   -0.7056    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789    1.1000    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329    0.5980    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3270    0.2569    0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    0.3086   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625    0.0388    1.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.0647   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.9803   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -2.1698   -0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    0.8601    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.8894    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5834    1.8118    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6867   -0.2185    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6200   -2.4006    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -2.3811    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967    0.4801   -3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8689    0.5984   -3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1454    0.6208   -2.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
M  END

Demethoxycurcumin
  Mrv1652309251700052D          

 25 26  0  0  0  0            999 V2000
   -4.8634   -8.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646   -9.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1498   -9.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -9.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362   -8.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -8.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5794   -9.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -8.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072   -8.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -7.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -8.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974   -7.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -7.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -8.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -7.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796   -8.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2801   -9.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953   -9.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -9.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -8.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -7.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4258   -9.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148   -7.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1324   -8.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
 11 13  1  0  0  0  0
  1  2  2  0  0  0  0
 13 14  1  0  0  0  0
  2  7  1  0  0  0  0
 13 15  2  0  0  0  0
  3  4  2  0  0  0  0
 14 16  2  0  0  0  0
  5  8  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  8  9  2  0  0  0  0
 18 19  1  0  0  0  0
  4  5  1  0  0  0  0
 19 20  2  0  0  0  0
  9 10  1  0  0  0  0
 20 21  1  0  0  0  0
  2  3  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 10 11  1  0  0  0  0
 20 23  1  0  0  0  0
  5  6  2  0  0  0  0
 21 24  1  0  0  0  0
 10 12  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033801

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

> <INCHI_KEY>
HJTVQHVGMGKONQ-LUZURFALSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.3539

> <EXACT_MASS>
338.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.35209001173169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.2821958166666665

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.442798697083019

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.837231925636592

> <JCHEM_PKA_STRONGEST_BASIC>
-4.477476498895879

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
97.34740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033801
     RDKit          3D
Demethoxycurcumin
 43 44  0  0  0  0  0  0  0  0999 V2000
   -6.4414    0.3018    2.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8632    0.3625    0.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9709    0.3940   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131    0.3297   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    0.3569   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2505    0.2470   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949    0.0909    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.0221    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.1773    1.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984    0.0358   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -1.1731   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -2.2717   -0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9336   -1.2023   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -0.1328    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -0.2338    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    0.9276    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0541    0.9056    1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -0.3198    1.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0436   -0.3454    1.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0510   -1.4847    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -1.4304    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817    0.4541   -2.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5218    0.5218   -2.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4268    0.4908   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7795    0.5517   -1.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0492   -0.7056    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789    1.1000    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329    0.5980    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3270    0.2569    0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    0.3086   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625    0.0388    1.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.0647   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.9803   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -2.1698   -0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    0.8601    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.8894    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5834    1.8118    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6867   -0.2185    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6200   -2.4006    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -2.3811    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967    0.4801   -3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8689    0.5984   -3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1454    0.6208   -2.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
M  END

HEADER    PROTEIN                                 25-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Demethoxycurcumin                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-17         0                                  
HETATM    1  C   UNK     0      -9.078 -15.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.081 -17.269   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.746 -18.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.409 -17.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.414 -15.718   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.750 -14.954   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -10.415 -18.038   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.083 -14.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.747 -15.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.416 -14.933   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.079 -15.698   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.422 -13.393   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.251 -14.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.588 -15.688   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.246 -13.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.919 -14.913   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.255 -15.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.256 -17.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.591 -17.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.924 -17.202   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.913 -15.654   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.577 -14.896   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.262 -17.965   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.241 -14.874   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.580 -15.635   0.000  0.00  0.00           C+0
CONECT    1    6    2                                                       
CONECT    2    1    7    3                                                  
CONECT    3    4    2                                                       
CONECT    4    3    5                                                       
CONECT    5    8    4    6                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   13   10                                                       
CONECT   12   10                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   21   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0033801
HETATM    1  C1  UNL     1      -6.441   0.302   2.074  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.863   0.362   0.750  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.971   0.394  -0.307  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.613   0.330  -0.049  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.695   0.357  -1.050  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.250   0.247  -0.825  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.695   0.091   0.329  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.290  -0.022   0.575  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.114  -0.177   1.766  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.698   0.036  -0.532  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.536  -1.173  -0.476  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.938  -2.272  -0.764  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.934  -1.202  -0.132  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.633  -0.133   0.183  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.035  -0.234   0.518  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.724   0.928   0.863  1.00  0.00           C  
HETATM   17  C14 UNL     1       7.054   0.906   1.190  1.00  0.00           C  
HETATM   18  C15 UNL     1       7.702  -0.320   1.168  1.00  0.00           C  
HETATM   19  O4  UNL     1       9.044  -0.345   1.497  1.00  0.00           O  
HETATM   20  C16 UNL     1       7.051  -1.485   0.832  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.689  -1.430   0.502  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.182   0.454  -2.344  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.522   0.522  -2.661  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.427   0.491  -1.627  1.00  0.00           C  
HETATM   25  O5  UNL     1      -7.780   0.552  -1.837  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.049  -0.706   2.362  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.679   1.100   2.239  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.333   0.598   2.700  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.327   0.257   0.985  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.626   0.309  -1.725  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.363   0.039   1.211  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.254   0.065  -1.543  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.280   0.980  -0.418  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.414  -2.170  -0.139  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.162   0.860   0.196  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.208   1.889   0.880  1.00  0.00           H  
HETATM   37  H12 UNL     1       7.583   1.812   1.458  1.00  0.00           H  
HETATM   38  H13 UNL     1       9.687  -0.218   0.700  1.00  0.00           H  
HETATM   39  H14 UNL     1       7.620  -2.401   0.835  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.258  -2.381   0.251  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.497   0.480  -3.176  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.869   0.598  -3.699  1.00  0.00           H  
HETATM   43  H18 UNL     1      -8.145   0.621  -2.758  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6   22   22
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   10
CONECT   10   11   32   33
CONECT   11   12   12   13
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16   21
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   20
CONECT   19   38
CONECT   20   21   21   39
CONECT   21   40
CONECT   22   23   41
CONECT   23   24   24   42
CONECT   24   25
CONECT   25   43
END

HMDB0033801
     RDKit          3D
Demethoxycurcumin
 43 44  0  0  0  0  0  0  0  0999 V2000
   -6.4414    0.3018    2.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8632    0.3625    0.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9709    0.3940   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131    0.3297   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    0.3569   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2505    0.2470   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949    0.0909    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.0221    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.1773    1.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984    0.0358   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -1.1731   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -2.2717   -0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9336   -1.2023   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6326   -0.1328    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -0.2338    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243    0.9276    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0541    0.9056    1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -0.3198    1.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0436   -0.3454    1.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0510   -1.4847    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -1.4304    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817    0.4541   -2.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5218    0.5218   -2.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4268    0.4908   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7795    0.5517   -1.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0492   -0.7056    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789    1.1000    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329    0.5980    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3270    0.2569    0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    0.3086   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625    0.0388    1.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.0647   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.9803   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -2.1698   -0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    0.8601    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.8894    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5834    1.8118    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6867   -0.2185    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6200   -2.4006    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -2.3811    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967    0.4801   -3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8689    0.5984   -3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1454    0.6208   -2.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione	ChEBI
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione	ChEBI
4-Hydroxycinnamoyl(feroyl)methane	ChEBI
4-Hydroxycinnamoyl(feruloyl)methane	ChEBI
BHCFM	ChEBI
CurcuminII	ChEBI
Feruloyl-p-hydroxycinnnamoylmethane	ChEBI
Monodemethoxycurcumin	MeSH
Curcumin II	MeSH
Demethoxy-curcumin	MeSH
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9ci	HMDB
P-Hydroxycinnamoylferuloylmethane	HMDB

Chemical Formula

C₂₀H₁₈O₅

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

IUPAC Name

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

Traditional Name

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

CAS Registry Number

22608-11-3

SMILES

COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

InChI Key

HJTVQHVGMGKONQ-LUZURFALSA-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

Desmethoxycurcumin
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
1,3-diketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enone (CHEBI:65737 )
polyphenol (CHEBI:65737 )
beta-diketone (CHEBI:65737 )
diarylheptanoid (CHEBI:65737 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033801)
Cell membrane (HMDB: HMDB0033801)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033801)

Source

Exogenous

Exogenous (HMDB: HMDB0033801)

Food

Food (HMDB: HMDB0033801)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033801)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033801)
Antiangiogenic (HMDB: HMDB0033801)
Antiangiogenic (HMDB: HMDB0033801)
Anti aflatoxin (HMDB: HMDB0033801)
Anti Alzheimeran (HMDB: HMDB0033801)
Anti amyloid-beta (HMDB: HMDB0033801)
Anti-inflammatory (HMDB: HMDB0033801)
Anti leishmanic (HMDB: HMDB0033801)
Anti lipoperoxidant (HMDB: HMDB0033801)
Anti mutagenic (HMDB: HMDB0033801)
Anti nitrosating (HMDB: HMDB0033801)
Anti papillomic (HMDB: HMDB0033801)
DNA-protective (HMDB: HMDB0033801)
Nitric-oxide scavenger (HMDB: HMDB0033801)
Plasmodicide (HMDB: HMDB0033801)
Quinone-reductase inducer (HMDB: HMDB0033801)

Modulator

Inhibitor

EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0033801)
Topoisomerase-II inhibitor (HMDB: HMDB0033801)

Enzyme inhibitor

Sortase-A inhibitor (HMDB: HMDB0033801)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor promoter (HMDB: HMDB0033801)

Agriculture

Pesticide

Nematicide (HMDB: HMDB0033801)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 °C	Not Available
Boiling Point	571.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	30.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.150 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0067 g/L	ALOGPS
logP	3.54	ALOGPS
logP	4.28	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.35 m³·mol⁻¹	ChemAxon
Polarizability	35.35 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]+	177.104	30932474
DeepCCS	[M-H]-	174.746	30932474
DeepCCS	[M-2H]-	208.971	30932474
DeepCCS	[M+Na]+	184.326	30932474
AllCCS	[M+H]+	184.2	32859911
AllCCS	[M+H-H2O]+	180.7	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.3	32859911
AllCCS	[M-H]-	180.8	32859911
AllCCS	[M+Na-2H]-	180.9	32859911
AllCCS	[M+HCOO]-	181.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demethoxycurcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O	5671.3	Standard polar	33892256
Demethoxycurcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O	3245.5	Standard non polar	33892256
Demethoxycurcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O	3622.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Demethoxycurcumin,1TMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O	3373.1	Semi standard non polar	33892256
Demethoxycurcumin,1TMS,isomer #2	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C	3364.1	Semi standard non polar	33892256
Demethoxycurcumin,1TMS,isomer #3	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O	3621.5	Semi standard non polar	33892256
Demethoxycurcumin,1TMS,isomer #4	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O	3600.9	Semi standard non polar	33892256
Demethoxycurcumin,2TMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3437.4	Semi standard non polar	33892256
Demethoxycurcumin,2TMS,isomer #2	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O	3593.3	Semi standard non polar	33892256
Demethoxycurcumin,2TMS,isomer #3	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O	3591.5	Semi standard non polar	33892256
Demethoxycurcumin,2TMS,isomer #4	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3605.1	Semi standard non polar	33892256
Demethoxycurcumin,2TMS,isomer #5	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3586.0	Semi standard non polar	33892256
Demethoxycurcumin,3TMS,isomer #1	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3620.9	Semi standard non polar	33892256
Demethoxycurcumin,3TMS,isomer #1	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3591.0	Standard non polar	33892256
Demethoxycurcumin,3TMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3617.6	Semi standard non polar	33892256
Demethoxycurcumin,3TMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3588.4	Standard non polar	33892256
Demethoxycurcumin,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	3682.1	Semi standard non polar	33892256
Demethoxycurcumin,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3650.6	Semi standard non polar	33892256
Demethoxycurcumin,1TBDMS,isomer #3	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3891.7	Semi standard non polar	33892256
Demethoxycurcumin,1TBDMS,isomer #4	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3864.9	Semi standard non polar	33892256
Demethoxycurcumin,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4003.6	Semi standard non polar	33892256
Demethoxycurcumin,2TBDMS,isomer #2	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	4184.0	Semi standard non polar	33892256
Demethoxycurcumin,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	4180.1	Semi standard non polar	33892256
Demethoxycurcumin,2TBDMS,isomer #4	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4150.8	Semi standard non polar	33892256
Demethoxycurcumin,2TBDMS,isomer #5	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4131.7	Semi standard non polar	33892256
Demethoxycurcumin,3TBDMS,isomer #1	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4401.5	Semi standard non polar	33892256
Demethoxycurcumin,3TBDMS,isomer #1	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4207.2	Standard non polar	33892256
Demethoxycurcumin,3TBDMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4401.9	Semi standard non polar	33892256
Demethoxycurcumin,3TBDMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4208.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Demethoxycurcumin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r2-0901000000-654fca3f02d69e7560db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethoxycurcumin GC-MS (2 TMS) - 70eV, Positive	splash10-014i-3071900000-50aab8ffd9b366fd14d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethoxycurcumin 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 - Demethoxycurcumin 50V, Positive-QTOF	splash10-0002-0900000000-9517befe911ff515a392	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOF	splash10-000i-0239000000-696b9f742f1375d511b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 30V, Negative-QTOF	splash10-014i-0910000000-9ba8139233df2e7399cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOF	splash10-014i-0920000000-d6ec1db1bc78454ca02e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 30V, Positive-QTOF	splash10-002b-0910000000-2b60408614dbac128af7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOF	splash10-0002-0900000000-5fbd4f101ab8f66c229a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOF	splash10-0a6s-0961000000-682f6b15c69a852c5c25	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOF	splash10-000i-0219000000-e3bd2864892e4f6e2318	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOF	splash10-014i-0910000000-dc9c78751e44dd920a70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Demethoxycurcumin 50V, Negative-QTOF	splash10-014i-0900000000-0a19a373bd22907fff2f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOF	splash10-000i-0419000000-127d78c62fb7431896b5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOF	splash10-002b-0901000000-c40b24a8778d2fa9787d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOF	splash10-002b-1900000000-82aa8b73d450c54c4c30	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOF	splash10-000i-0309000000-1e9e9a7c9cdc0d078ad5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOF	splash10-000j-0914000000-656374264de68ab93dd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOF	splash10-07xs-1911000000-d77a4b8103374473002f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOF	splash10-000i-0709000000-d28143d2357c12a71e64	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOF	splash10-0002-0901000000-071370f22d66d14d47d2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOF	splash10-014j-1910000000-dbecc05d29e924e0b535	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOF	splash10-014i-0952000000-238d293f45f85e124a77	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOF	splash10-014r-0913000000-2bcebdb0a036193118c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOF	splash10-014r-0912000000-46bf9193d3b8351d3505	2021-09-25	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-12187

BiGG ID

Not Available

Wikipedia Link

Desmethoxycurcumin

METLIN ID

Not Available

PubChem Compound

5469424

PDB ID

Not Available

ChEBI ID

65737

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486801

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Villaflores OB, Chen YJ, Chen CP, Yeh JM, Wu TY: Effects of curcumin and demethoxycurcumin on amyloid-beta precursor and tau proteins through the internal ribosome entry sites: a potential therapeutic for Alzheimer's disease. Taiwan J Obstet Gynecol. 2012 Dec;51(4):554-64. doi: 10.1016/j.tjog.2012.09.010. [PubMed:23276558 ]
Chaneiam N, Changtam C, Mungkongdee T, Suthatvoravut U, Winichagoon P, Vadolas J, Suksamrarn A, Fucharoen S, Svasti S: A reduced curcuminoid analog as a novel inducer of fetal hemoglobin. Ann Hematol. 2013 Mar;92(3):379-86. doi: 10.1007/s00277-012-1604-1. Epub 2012 Oct 19. [PubMed:23079892 ]
Jitoe-Masuda A, Fujimoto A, Masuda T: Curcumin: from chemistry to chemistry-based functions. Curr Pharm Des. 2013;19(11):2084-92. [PubMed:23116314 ]
Villaflores OB, Chen YJ, Chen CP, Yeh JM, Wu TY: Curcuminoids and resveratrol as anti-Alzheimer agents. Taiwan J Obstet Gynecol. 2012 Dec;51(4):515-25. doi: 10.1016/j.tjog.2012.09.005. [PubMed:23276553 ]
Jantan I, Saputri FC, Qaisar MN, Buang F: Correlation between Chemical Composition of Curcuma domestica and Curcuma xanthorrhiza and Their Antioxidant Effect on Human Low-Density Lipoprotein Oxidation. Evid Based Complement Alternat Med. 2012;2012:438356. doi: 10.1155/2012/438356. Epub 2012 Nov 26. [PubMed:23243446 ]
Kumar A, Bora U: Molecular docking studies on inhibition of Stat3 dimerization by curcumin natural derivatives and its conjugates with amino acids. Bioinformation. 2012;8(20):988-93. doi: 10.6026/97320630008988. Epub 2012 Oct 13. [PubMed:23275693 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Demethoxycurcumin (HMDB0033801)

MOL for HMDB0033801 (Demethoxycurcumin)

3D MOL for HMDB0033801 (Demethoxycurcumin)

3D SDF for HMDB0033801 (Demethoxycurcumin)

3D-SDF for HMDB0033801 (Demethoxycurcumin)

PDB for HMDB0033801 (Demethoxycurcumin)

3D PDB for HMDB0033801 (Demethoxycurcumin)

SMILES for HMDB0033801 (Demethoxycurcumin)

INCHI for HMDB0033801 (Demethoxycurcumin)

Structure for HMDB0033801 (Demethoxycurcumin)

3D Structure for HMDB0033801 (Demethoxycurcumin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra