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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002269

Secondary Accession Numbers

HMDB02269

Metabolite Identification

Common Name

Curcumin

Description

Curcumin is a natural component of the rhizome of turmeric (Curcuma longa) and one of the most powerful chemopreventive and anticancer agents. Its biological effects range from antioxidant, anti-inflammatory to inhibition of angiogenesis and is also shown to possess specific antitumoral activity. The molecular mechanism of its varied cellular effects has been studied in some details and it has been shown to have multiple targets and interacting macromolecules within the cell. Curcumin has been shown to possess anti-angiogenic properties and the angioinhibitory effects of curcumin manifest due to down regulation of proangiogenic genes such as VEGF and angiopoitin and a decrease in migration and invasion of endothelial cells. One of the important factors implicated in chemoresistance and induced chemosensitivity is NFkB and curcumin has been shown to down regulate NFkB and inhibit IKB kinase thereby suppressing proliferation and inducing apoptosis. Cell lines that are resistant to certain apoptotic inducers and radiation become susceptible to apoptosis when treated in conjunction with curcumin. Besides this it can also act as a chemopreventive agent in cancers of colon, stomach and skin by suppressing colonic aberrant crypt foci formation and DNA adduct formation. This review focuses on the various aspects of curcumin as a potential drug for cancer treatment and its implications in a variety of biological and cellular processes vis-à-vis its mechanism of action (PMID: 16712454 ). Turmeric (Zingiberaceae family) rhizomes, has been widely used for centuries in indigenous medicine for the treatment of a variety of inflammatory conditions and other diseases. Its medicinal properties have been attributed mainly to the curcuminoids and the main component present in the rhizome is curcumin. Curcumin has been shown to possess wide range of pharmacological activities including anti-inflammatory, anti-cancer, anti-oxidant, wound healing and anti-microbial effects. Recently, curcumin treatment has been shown to correct defects associated with cystic fibrosis in homozygous DeltaF508 cystic fibrosis transmembrane conductance regulator (CFTR) knock out mice. In vivo and in vitro studies have demonstrated curcumin's ability to inhibit carcinogenesis at three stages: tumor promotion, angiogenesis and tumor growth. Curcumin suppresses mitogen-induced proliferation of blood mononuclear cells, inhibits neutrophil activation and mixed lymphocyte reaction and also inhibits both serum-induced and platelet derived growth factor (PDGF)-dependent mitogenesis of smooth muscle cells. It has also been reported to be a partial inhibitor of protein kinase. The other salient feature of turmeric/curcumin is that despite being consumed daily for centuries in Asian countries, it has not been shown to cause any toxicity (PMID: 16413584 ).

Structure

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

HMDB02269.mol
  Mrv0541 02231219272D          

 27 28  0  0  0  0            999 V2000
   -4.2907    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8624   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8624    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -1.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
  8 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END

HMDB0002269
     RDKit          3D
Curcumin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -5.8042   -0.3397   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2382   -1.1425   -1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5374   -1.1585   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024   -0.4017   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.4233    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    0.3963    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7747    0.4592    2.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    1.3163    2.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.3611    3.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    2.1465    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    2.9094    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004    4.0059    2.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    2.5143    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    1.4010    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100    0.9593    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.6553    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    1.1401   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742   -0.0410   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -0.5268   -1.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -0.7577   -1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330   -1.9466   -1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594   -2.7007   -2.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.2355   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057   -1.2381    1.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -2.0089    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0293   -1.9808    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1690   -2.7345    0.3877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114    0.6652   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9744   -0.8230   -3.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6579   -0.2391   -3.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    0.2458   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829    1.0171    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.1350    3.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    1.5399    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    2.8690    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    3.1442    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    0.8031    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095    2.5783    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2703    1.7271    0.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5391    0.0069   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006   -2.8022   -1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398   -2.0685   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -3.6844   -2.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216   -0.8252   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087   -1.2945    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790   -2.6283    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6732   -2.7250   -0.4660 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  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 23 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
M  END

HMDB02269.mol
  Mrv0541 02231219272D          

 27 28  0  0  0  0            999 V2000
   -4.2907    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8624   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8624    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766   -1.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
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 15 17  2  0  0  0  0
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 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
  8 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002269

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+

> <INCHI_KEY>
VFLDPWHFBUODDF-FCXRPNKRSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.3799

> <EXACT_MASS>
368.125988372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
38.12302565425179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
4.1245245509999995

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.583124219322876

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.061334054864934

> <JCHEM_PKA_STRONGEST_BASIC>
-4.355207917811037

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
103.8106

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
curcumin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002269
     RDKit          3D
Curcumin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -5.8042   -0.3397   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2382   -1.1425   -1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5374   -1.1585   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024   -0.4017   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.4233    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    0.3963    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7747    0.4592    2.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    1.3163    2.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.3611    3.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    2.1465    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    2.9094    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004    4.0059    2.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    2.5143    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    1.4010    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100    0.9593    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.6553    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    1.1401   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742   -0.0410   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -0.5268   -1.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -0.7577   -1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330   -1.9466   -1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594   -2.7007   -2.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.2355   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057   -1.2381    1.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -2.0089    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0293   -1.9808    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1690   -2.7345    0.3877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114    0.6652   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9744   -0.8230   -3.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6579   -0.2391   -3.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    0.2458   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829    1.0171    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.1350    3.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    1.5399    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    2.8690    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    3.1442    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    0.8031    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095    2.5783    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2703    1.7271    0.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5391    0.0069   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006   -2.8022   -1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398   -2.0685   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -3.6844   -2.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216   -0.8252   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087   -1.2945    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790   -2.6283    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6732   -2.7250   -0.4660 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  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 23 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB02269.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.009   1.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.009  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.676  -1.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.343  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.343   1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.676   1.927   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.342  -1.156   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.676  -2.698   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.005   1.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.672   1.156   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.333   1.927   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.156   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.333   3.469   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.338   1.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.672   1.156   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.338   3.469   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.010   1.927   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.348   1.156   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.348  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.682  -1.156   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.009  -0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.009   1.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.682   1.927   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.682  -2.698   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.348  -1.156   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.009  -3.469   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.015  -3.469   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    3   26                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   20   27                                                       
CONECT   25   21                                                            
CONECT   26    8                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0002269
HETATM    1  C1  UNL     1      -5.804  -0.340  -2.678  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.238  -1.142  -1.612  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.537  -1.158  -0.419  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.402  -0.402  -0.225  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.706  -0.423   0.975  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.511   0.396   1.129  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.775   0.459   2.211  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.588   1.316   2.268  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.103   1.361   3.316  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.164   2.147   1.116  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.042   2.909   1.422  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.900   4.006   2.061  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.412   2.514   1.053  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.678   1.401   0.395  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.010   0.959   0.003  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.162   1.655   0.275  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.387   1.140  -0.148  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.474  -0.041  -0.826  1.00  0.00           C  
HETATM   19  O4  UNL     1       7.712  -0.527  -1.233  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.312  -0.758  -1.109  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.433  -1.947  -1.795  1.00  0.00           O  
HETATM   22  C17 UNL     1       4.259  -2.701  -2.099  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.114  -0.235  -0.685  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.206  -1.238   1.960  1.00  0.00           C  
HETATM   25  C20 UNL     1      -5.348  -2.009   1.786  1.00  0.00           C  
HETATM   26  C21 UNL     1      -6.029  -1.981   0.596  1.00  0.00           C  
HETATM   27  O6  UNL     1      -7.169  -2.734   0.388  1.00  0.00           O  
HETATM   28  H1  UNL     1      -5.511   0.665  -2.338  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.974  -0.823  -3.255  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.658  -0.239  -3.391  1.00  0.00           H  
HETATM   31  H4  UNL     1      -4.013   0.246  -1.021  1.00  0.00           H  
HETATM   32  H5  UNL     1      -2.183   1.017   0.286  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.060  -0.135   3.065  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.094   1.540   0.194  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.994   2.869   0.934  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.248   3.144   1.321  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.789   0.803   0.152  1.00  0.00           H  
HETATM   38  H11 UNL     1       5.110   2.578   0.803  1.00  0.00           H  
HETATM   39  H12 UNL     1       7.270   1.727   0.091  1.00  0.00           H  
HETATM   40  H13 UNL     1       8.539   0.007  -1.019  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.701  -2.802  -1.128  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.640  -2.069  -2.765  1.00  0.00           H  
HETATM   43  H16 UNL     1       4.509  -3.684  -2.526  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.222  -0.825  -0.924  1.00  0.00           H  
HETATM   45  H18 UNL     1      -3.709  -1.295   2.906  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.679  -2.628   2.615  1.00  0.00           H  
HETATM   47  H20 UNL     1      -7.673  -2.725  -0.466  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   31
CONECT    5    6   24   24
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11   34   35
CONECT   11   12   12   13
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   16   23
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   41   42   43
CONECT   23   44
CONECT   24   25   45
CONECT   25   26   26   46
CONECT   26   27
CONECT   27   47
END

HMDB0002269
     RDKit          3D
Curcumin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -5.8042   -0.3397   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2382   -1.1425   -1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5374   -1.1585   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024   -0.4017   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.4233    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    0.3963    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7747    0.4592    2.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    1.3163    2.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.3611    3.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    2.1465    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    2.9094    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004    4.0059    2.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    2.5143    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    1.4010    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100    0.9593    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.6553    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    1.1401   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742   -0.0410   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -0.5268   -1.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -0.7577   -1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330   -1.9466   -1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594   -2.7007   -2.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.2355   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057   -1.2381    1.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -2.0089    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0293   -1.9808    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1690   -2.7345    0.3877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114    0.6652   -2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9744   -0.8230   -3.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6579   -0.2391   -3.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    0.2458   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829    1.0171    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.1350    3.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    1.5399    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    2.8690    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477    3.1442    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    0.8031    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095    2.5783    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2703    1.7271    0.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5391    0.0069   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006   -2.8022   -1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398   -2.0685   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -3.6844   -2.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216   -0.8252   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087   -1.2945    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790   -2.6283    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6732   -2.7250   -0.4660 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  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 23 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C.I. 75300	ChEBI
C.I. natural yellow 3	ChEBI
Diferuloylmethane	ChEBI
e 100	ChEBI
Kacha haldi	ChEBI
Natural yellow 3	ChEBI
Turmeric yellow	ChEBI
Yellow, turmeric	MeSH
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione	HMDB
1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione	HMDB
1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dione	HMDB
CI natural yellow 3	HMDB
Cucurmin	HMDB
Curcuma	HMDB
Curcumin I	HMDB
Diferaloylmethane	HMDB
Gelbwurz	HMDB
Golden seal	HMDB
Haidr	HMDB
Halad	HMDB
Haldar	HMDB
Halud	HMDB
Hydrastis	HMDB
Merita earth	HMDB
Orange root	HMDB
Safran d'inde	HMDB
Souchet	HMDB
Terra merita	HMDB
Tumeric yellow	HMDB
Turmeric	HMDB
Turmeric (>98% curcurmin)	HMDB
Turmeric oleoresin (79%-85% curcumin)	HMDB
Yellow ginger	HMDB
Yellow puccoon	HMDB
Yellow root	HMDB
yo-Kin	HMDB

Chemical Formula

C₂₁H₂₀O₆

Average Molecular Weight

368.3799

Monoisotopic Molecular Weight

368.125988372

IUPAC Name

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

Traditional Name

curcumin

CAS Registry Number

458-37-7

SMILES

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

InChI Identifier

InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+

InChI Key

VFLDPWHFBUODDF-FCXRPNKRSA-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

Curcumin
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

aromatic ether (CHEBI:3962 )
enone (CHEBI:3962 )
polyphenol (CHEBI:3962 )
beta-diketone (CHEBI:3962 )
diarylheptanoid (CHEBI:3962 )

Ontology

Disposition

Biological location

Non-excretory biofluid

Blood

Excreta

Feces

Herb and spice mixtures

Curry powder

Teas

Herbal tea

Herbal teas

Greenthread tea

Lentils

Onion-family vegetables

Cabbages

Other vegetables

Mushrooms

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Cocoa and cocoa products

Cocoa

Cocoa bean

Soy bean

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.48 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.290 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	201.635	30932474
[M+H]+	Not Available	200.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000434

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0058 g/L	ALOGPS
logP	3.62	ALOGPS
logP	4.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.81 m³·mol⁻¹	ChemAxon
Polarizability	38.12 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]+	183.151	30932474
DeepCCS	[M-H]-	180.793	30932474
DeepCCS	[M-2H]-	214.857	30932474
DeepCCS	[M+Na]+	190.157	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O	6157.5	Standard polar	33892256
Curcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O	3412.0	Standard non polar	33892256
Curcumin	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O	3701.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcumin,1TMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3591.7	Semi standard non polar	33892256
Curcumin,1TMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O	3763.2	Semi standard non polar	33892256
Curcumin,2TMS,isomer #1	COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	3620.2	Semi standard non polar	33892256
Curcumin,2TMS,isomer #2	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O	3742.2	Semi standard non polar	33892256
Curcumin,2TMS,isomer #3	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O	3743.5	Semi standard non polar	33892256
Curcumin,3TMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3774.2	Semi standard non polar	33892256
Curcumin,3TMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3704.2	Standard non polar	33892256
Curcumin,3TMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3940.6	Standard polar	33892256
Curcumin,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(OC)=C2)=CC=C1O	3877.1	Semi standard non polar	33892256
Curcumin,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	4053.2	Semi standard non polar	33892256
Curcumin,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(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4170.8	Semi standard non polar	33892256
Curcumin,2TBDMS,isomer #2	COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	4324.1	Semi standard non polar	33892256
Curcumin,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(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	4325.9	Semi standard non polar	33892256
Curcumin,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4536.5	Semi standard non polar	33892256
Curcumin,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4318.6	Standard non polar	33892256
Curcumin,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4091.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Curcumin EI-B (Non-derivatized)	splash10-0fbc-0923000000-107f42bbc825be91449b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Curcumin EI-B (Non-derivatized)	splash10-0fbc-0923000000-107f42bbc825be91449b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0902000000-a583c69443735ecee34d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumin GC-MS (2 TMS) - 70eV, Positive	splash10-006t-3090600000-d97f58b9779a3d4c58d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumin 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 - Curcumin LC-ESI-ITTOF , negative-QTOF	splash10-0600-0920000000-c006d38848959c621ec5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin LC-ESI-QTOF , negative-QTOF	splash10-014i-0982000000-2c508f0e4a39ae290728	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin LC-ESI-QTOF , negative-QTOF	splash10-00di-0950000000-af821cd7589af1e24d16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin LC-ESI-QTOF , negative-QTOF	splash10-0fk9-0981000000-e4da18f81a545b08874b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin , positive-QTOF	splash10-002b-2920000000-3c3aa8613bf16651cdf5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 20V, Negative-QTOF	splash10-000t-0911000000-abf0df68155c943697d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 40V, Negative-QTOF	splash10-001i-0900000000-0a0213a836a78f6e54cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 10V, Positive-QTOF	splash10-03k9-0169000000-ba031996da79b96e1951	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 40V, Positive-QTOF	splash10-004r-0960000000-f8dd0033b656ce57faaa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 20V, Positive-QTOF	splash10-00di-0291000000-2396d815134514f2f735	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Curcumin 10V, Negative-QTOF	splash10-014j-0982000000-9cbccf58679bdd2133ef	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 10V, Positive-QTOF	splash10-014i-0209000000-f995da101a08357914b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 20V, Positive-QTOF	splash10-004i-0913000000-6bece31c8c8078c2fda4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 40V, Positive-QTOF	splash10-004j-1900000000-6706d488783638730883	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 10V, Negative-QTOF	splash10-014i-0109000000-3cbd5e4d9320bc54c318	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 20V, Negative-QTOF	splash10-014i-0729000000-ae0fe93ebdfbeed7cc4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 40V, Negative-QTOF	splash10-004v-0914000000-72385474a47d42818f05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 10V, Negative-QTOF	splash10-014i-0419000000-9ca31d2513afa0489fab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 20V, Negative-QTOF	splash10-00ls-0924000000-a7bc7daf4e9622a19a4b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 40V, Negative-QTOF	splash10-008j-0922000000-5ce00b7393b9b7b00d5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 10V, Positive-QTOF	splash10-016r-0609000000-79fd92244350d542a9f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 20V, Positive-QTOF	splash10-0171-0955000000-d16b5d995679749aff17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumin 40V, Positive-QTOF	splash10-002k-1943000000-404ab5fc28a3d651940e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.17 +/- 0.013 uM	Adult (>18 years old)	Both	Normal	12450549	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB11672

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Curcumin

METLIN ID

Not Available

PubChem Compound

969516

PDB ID

Not Available

ChEBI ID

3962

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1232091

References

Synthesis Reference

Wehrli, Christof. Curcumin synthesis. PCT Int. Appl. (2007), 11pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Singh S, Khar A: Biological effects of curcumin and its role in cancer chemoprevention and therapy. Anticancer Agents Med Chem. 2006 May;6(3):259-70. [PubMed:16712454 ]
Maheshwari RK, Singh AK, Gaddipati J, Srimal RC: Multiple biological activities of curcumin: a short review. Life Sci. 2006 Mar 27;78(18):2081-7. Epub 2006 Jan 18. [PubMed:16413584 ]

Showing metabocard for Curcumin (HMDB0002269)

MOL for HMDB0002269 (Curcumin)

3D MOL for HMDB0002269 (Curcumin)

3D SDF for HMDB0002269 (Curcumin)

3D-SDF for HMDB0002269 (Curcumin)

PDB for HMDB0002269 (Curcumin)

3D PDB for HMDB0002269 (Curcumin)

SMILES for HMDB0002269 (Curcumin)

INCHI for HMDB0002269 (Curcumin)

Structure for HMDB0002269 (Curcumin)

3D Structure for HMDB0002269 (Curcumin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra