MiMeDB: Showing metabocard for Tetrahydrocurcumin (MMDBc0031152)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:37:26 UTC

Update Date

2022-08-31 17:58:56 UTC

Metabolite ID

MMDBc0031152

Metabolite Identification

Common Name

Tetrahydrocurcumin

Description

Tetrahydrocurcumin (THC), is a product of the metabolism of curcumin by the enzyme NADPH-dependent curcumin reductase. 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 curcumin 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


  Mrv0541 02231220292D          

 27 28  0  0  0  0            999 V2000
   14.2176  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9801  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2176  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6301  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4551  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8676  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6926  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1051  -11.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1051  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9301  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3426  -11.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3426  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5802  -14.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -14.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5802  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9801  -11.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -10.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6427  -14.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0552  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1551  -12.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177  -16.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 21 17  2  0  0  0  0
 22  4  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26  3  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

HMDB0005789
     RDKit          3D
Tetrahydrocurcumin
 51 52  0  0  0  0  0  0  0  0999 V2000
    7.9185   -0.2988   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4582    1.0260   -0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523    1.3734   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992    0.3954    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953    0.7192    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2727    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.9256   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -1.9022    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -3.0045    0.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0987   -1.5800    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0986   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -2.6925   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -1.8772   -0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8133   -1.1371    0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -0.9517    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1906   -1.8837    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5491   -1.7020    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005   -0.5472    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3704   -0.3101   -0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1290    0.4043   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6398    1.5377   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6972    2.4894   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7592    0.1889   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    2.0204    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425    2.9904   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    2.6759   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497    3.6140   -1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2261   -1.0224   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373   -0.5298    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9180   -0.4315   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177   -0.6149    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.2930    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195   -1.0342    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.4315   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -0.1847   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -2.0346    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -0.4832    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.3000   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -2.8538   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -0.2150    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -1.8193    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -2.7603    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2398   -2.4427    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7208    0.5052   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0349    2.8107   -0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2454    3.4277   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    2.0518   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.9447   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    2.2953    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385    4.0135   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3439    4.5654   -1.2054 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  1  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  1  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
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END


  Mrv0541 02231220292D          

 27 28  0  0  0  0            999 V2000
   14.2176  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9801  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2176  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6301  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4551  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8676  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6926  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1051  -11.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1051  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9301  -12.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3426  -11.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3426  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5802  -14.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -14.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5802  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9801  -11.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926  -10.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6427  -14.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0552  -15.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1551  -12.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177  -16.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 21 17  2  0  0  0  0
 22  4  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26  3  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031152

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/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/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3

> <INCHI_KEY>
LBTVHXHERHESKG-UHFFFAOYSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.4117

> <EXACT_MASS>
372.1572885

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
39.416017161143095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.963477571666666

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.884451516447372

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30754417747834

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590548905209303

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
101.624

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrocurcumin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005789
     RDKit          3D
Tetrahydrocurcumin
 51 52  0  0  0  0  0  0  0  0999 V2000
    7.9185   -0.2988   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4582    1.0260   -0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523    1.3734   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992    0.3954    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953    0.7192    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2727    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.9256   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -1.9022    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -3.0045    0.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0987   -1.5800    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0986   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -2.6925   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -1.8772   -0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8133   -1.1371    0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -0.9517    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1906   -1.8837    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5491   -1.7020    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005   -0.5472    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3704   -0.3101   -0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1290    0.4043   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6398    1.5377   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6972    2.4894   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7592    0.1889   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    2.0204    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425    2.9904   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    2.6759   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497    3.6140   -1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2261   -1.0224   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373   -0.5298    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9180   -0.4315   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177   -0.6149    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.2930    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195   -1.0342    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.4315   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -0.1847   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -2.0346    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -0.4832    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.3000   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -2.8538   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -0.2150    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -1.8193    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -2.7603    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2398   -2.4427    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7208    0.5052   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0349    2.8107   -0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2454    3.4277   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    2.0518   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.9447   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    2.2953    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385    4.0135   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3439    4.5654   -1.2054 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  1  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  1  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
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      26.540 -24.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.000 -24.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.230 -23.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.000 -22.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.540 -22.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.310 -23.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.850 -23.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.620 -22.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.160 -22.319   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.930 -20.986   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      31.930 -23.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.470 -23.653   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      34.240 -22.319   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      34.240 -24.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.780 -24.987   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.550 -26.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.090 -26.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.780 -27.654   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.550 -28.988   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.090 -28.988   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.860 -27.654   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      24.230 -20.986   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      25.000 -19.652   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      40.400 -27.654   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      41.170 -28.988   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      22.690 -23.653   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      38.860 -30.322   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   21                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   17   24                                                  
CONECT   22    4   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24                                                            
CONECT   26    3                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0005789
HETATM    1  C1  UNL     1       7.919  -0.299  -0.426  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.458   1.026  -0.629  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.152   1.373  -0.330  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.299   0.395   0.174  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.995   0.719   0.479  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.016  -0.273   1.021  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.305  -0.926  -0.154  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.340  -1.902   0.371  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.747  -3.005   0.700  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.099  -1.580   0.507  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.840  -2.099  -0.656  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.256  -2.693  -1.537  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.318  -1.877  -0.726  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.813  -1.137   0.499  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.277  -0.952   0.361  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.191  -1.884   0.833  1.00  0.00           C  
HETATM   17  C14 UNL     1      -6.549  -1.702   0.700  1.00  0.00           C  
HETATM   18  C15 UNL     1      -7.001  -0.547   0.073  1.00  0.00           C  
HETATM   19  O4  UNL     1      -8.370  -0.310  -0.089  1.00  0.00           O  
HETATM   20  C16 UNL     1      -6.129   0.404  -0.411  1.00  0.00           C  
HETATM   21  O5  UNL     1      -6.640   1.538  -1.028  1.00  0.00           O  
HETATM   22  C17 UNL     1      -5.697   2.489  -1.510  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.759   0.189  -0.259  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.598   2.020   0.264  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.443   2.990  -0.236  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.752   2.676  -0.544  1.00  0.00           C  
HETATM   27  O6  UNL     1       6.650   3.614  -1.052  1.00  0.00           O  
HETATM   28  H1  UNL     1       7.226  -1.022  -0.861  1.00  0.00           H  
HETATM   29  H2  UNL     1       8.037  -0.530   0.653  1.00  0.00           H  
HETATM   30  H3  UNL     1       8.918  -0.432  -0.879  1.00  0.00           H  
HETATM   31  H4  UNL     1       5.618  -0.615   0.339  1.00  0.00           H  
HETATM   32  H5  UNL     1       2.241   0.293   1.580  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.520  -1.034   1.621  1.00  0.00           H  
HETATM   34  H7  UNL     1       3.109  -1.432  -0.746  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.762  -0.185  -0.757  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.464  -2.035   1.465  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.239  -0.483   0.625  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.571  -1.300  -1.656  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.839  -2.854  -0.795  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.262  -0.215   0.689  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.646  -1.819   1.371  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.770  -2.760   1.309  1.00  0.00           H  
HETATM   43  H16 UNL     1      -7.240  -2.443   1.076  1.00  0.00           H  
HETATM   44  H17 UNL     1      -8.721   0.505  -0.534  1.00  0.00           H  
HETATM   45  H18 UNL     1      -5.035   2.811  -0.657  1.00  0.00           H  
HETATM   46  H19 UNL     1      -6.245   3.428  -1.796  1.00  0.00           H  
HETATM   47  H20 UNL     1      -5.123   2.052  -2.330  1.00  0.00           H  
HETATM   48  H21 UNL     1      -4.065   0.945  -0.643  1.00  0.00           H  
HETATM   49  H22 UNL     1       2.571   2.295   0.498  1.00  0.00           H  
HETATM   50  H23 UNL     1       4.139   4.014  -0.407  1.00  0.00           H  
HETATM   51  H24 UNL     1       6.344   4.565  -1.205  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   32   33
CONECT    7    8   34   35
CONECT    8    9    9   10
CONECT   10   11   36   37
CONECT   11   12   12   13
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   16   23
CONECT   16   17   42
CONECT   17   18   18   43
CONECT   18   19   20
CONECT   19   44
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   45   46   47
CONECT   23   48
CONECT   24   25   49
CONECT   25   26   26   50
CONECT   26   27
CONECT   27   51
END

HMDB0005789
     RDKit          3D
Tetrahydrocurcumin
 51 52  0  0  0  0  0  0  0  0999 V2000
    7.9185   -0.2988   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4582    1.0260   -0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523    1.3734   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992    0.3954    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953    0.7192    0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2727    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.9256   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -1.9022    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -3.0045    0.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0987   -1.5800    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0986   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -2.6925   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -1.8772   -0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8133   -1.1371    0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -0.9517    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1906   -1.8837    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5491   -1.7020    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005   -0.5472    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3704   -0.3101   -0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1290    0.4043   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6398    1.5377   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6972    2.4894   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7592    0.1889   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    2.0204    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425    2.9904   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    2.6759   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497    3.6140   -1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2261   -1.0224   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373   -0.5298    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9180   -0.4315   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177   -0.6149    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.2930    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195   -1.0342    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.4315   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -0.1847   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -2.0346    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -0.4832    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.3000   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -2.8538   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -0.2150    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -1.8193    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -2.7603    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2398   -2.4427    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7208    0.5052   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0349    2.8107   -0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2454    3.4277   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    2.0518   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.9447   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    2.2953    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385    4.0135   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3439    4.5654   -1.2054 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  1  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  1  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
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END

Synonyms

Not Available

Molecular Formula

C₂₁H₂₄O₆

Average Mass

372.4117

Monoisotopic Mass

372.1572885

IUPAC Name

1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione

Traditional Name

tetrahydrocurcumin

CAS Registry Number

36062-04-1

SMILES

COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C21H24O6/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/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3

InChI Key

LBTVHXHERHESKG-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	3.51	ALOGPS
logP	3.96	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.6	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	10	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	39.42 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	16.0	0.2				Adult (>18 years old)	Both	Normal	HMDB	16061427

External Links

Not Available

General References

Heath DD, Pruitt MA, Brenner DE, Begum AN, Frautschy SA, Rock CL: Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):206-12. doi: 10.1016/j.jchromb.2005.07.026. [PubMed:16061427 ]

Showing metabocard for Tetrahydrocurcumin (MMDBc0031152)

MOL for #<Metabolite:0x00007f12218f9410>

3D MOL for #<Metabolite:0x00007f12218f9410>

3D SDF for #<Metabolite:0x00007f12218f9410>

3D-SDF for #<Metabolite:0x00007f12218f9410>

PDB for #<Metabolite:0x00007f12218f9410>

3D PDB for #<Metabolite:0x00007f12218f9410>

SMILES for #<Metabolite:0x00007f12218f9410>

INCHI for #<Metabolite:0x00007f12218f9410>

Structure for #<Metabolite:0x00007f12218f9410>

3D Structure for #<Metabolite:0x00007f12218f9410>