MiMeDB: Showing metabocard for curcumin (MMDBc0031786)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:16 UTC

Update Date

2024-09-27 19:12:35 UTC

Metabolite ID

MMDBc0031786

Metabolite Identification

Common Name

curcumin

Description

Curcumin is a yellow, polyphenolic pigment, derived from the rhizomes of a plant (Curcuma longa Linn). It is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family and is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods.. In E. coli it is a substrate for the enzyme NADPH-dependent curcumin reductase which catalyzes the metal-independent reduction of curcumin to dihydrocurcumin (DHC) as an intermediate product, followed by further reduction to tetrahydrocurcumin (THC) as an end product. Tetrahydrocurcumin (THC) exhibits many of the same physiologic and pharmacological activities as curcumin and in some systems may exert greater antioxidant activity than curcumin [PMID:21467222 ]

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
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 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
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  6  7  2  0
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 23 15  1  0
  1 28  1  0
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  4 31  1  0
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 10 34  1  0
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 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
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    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
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  3  4  2  0  0  0  0
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 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031786

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₁H₂₀O₆

Average Mass

368.3799

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018877	curcumin	Dihydrocurcumin	NADPH-dependent curcumin reductase	Reduction	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.17	0.013			uM	Adult (>18 years old)	Both	Normal	HMDB	12450549

External Links

HMDB ID

HMDB0002269

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/j.lfs.2005.12.007. Epub 2006 Jan 18. [PubMed:16413584 ]
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. doi: 10.2174/187152006776930918. [PubMed:16712454 ]

Showing metabocard for curcumin (MMDBc0031786)

MOL for #<Metabolite:0x00007f91f65fdd38>

3D MOL for #<Metabolite:0x00007f91f65fdd38>

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Structure for #<Metabolite:0x00007f91f65fdd38>

3D Structure for #<Metabolite:0x00007f91f65fdd38>