MiMeDB: Showing metabocard for Catechin (MMDBc0033606)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:34 UTC

Update Date

2024-09-27 20:29:41 UTC

Metabolite ID

MMDBc0033606

Metabolite Identification

Common Name

Catechin

Description

Catechin, also known as cyanidanol or catechuic acid, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin also belongs to the group of compounds known as flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids. Catechin is one of the 4 catechin known diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin. The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound and is associated with the bitterness in tea. Catechin is a plant secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Catechin is an antioxidant flavonoid, occurring especially in woody plants as both Catechin and (-)-Catechin (cis) forms. Outside of the human body, Catechin is found, on average, in the highest concentration in foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in dills (Anethum graveolens), hot chocolates, and medlars (Mespilus germanica). Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), apple ciders, peanuts (Arachis hypogaea), fruit juices, and red teas. This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin.

Structure

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

HMDB0037953
     RDKit          3D
(-)-Catechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4015    2.6921   -1.2885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.6179   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.3705   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -0.7133   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477   -1.9291   -0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.5520    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657    0.7166    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483    1.7795   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    0.9076    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -0.1218    0.9542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7628    0.2598    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847    1.5100    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.8957    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    1.0352   -0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171    1.4485   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.2142   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5094   -1.1030   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5965   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959   -1.4026    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6412   -2.5113    0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -1.6054    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644    2.9199   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3243    0.2431   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891   -2.7168    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    2.7647   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -0.2300    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7238    2.1917    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    2.8741    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233    0.7799   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1151   -2.0170   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761   -1.5794   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -1.4269   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -3.3423    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -1.3201    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.6249    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv1652309272007282D          

 21 23  0  0  0  0            999 V2000
10001.0796 9998.5727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2236 9997.7423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.792310000.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.798410002.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.227610001.4694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.223710000.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5091 9999.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5091 9998.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2236 9998.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.510810001.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.796310001.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081810001.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081810000.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7962 9999.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.510810000.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651410000.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9369 9999.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9369 9998.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6514 9998.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3659 9998.9889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3659 9999.8140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 11  4  1  0  0  0  0
 10  5  1  0  0  0  0
  9  2  1  0  0  0  0
  7  3  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 20  1  1  1  0  0  0
 21 13  1  6  0  0  0
 17  6  2  0  0  0  0
  9 18  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033606

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

> <INCHI_KEY>
PFTAWBLQPZVEMU-DZGCQCFKSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.8872798853884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.795107015333333

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.624022697297178

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.004573813837975

> <JCHEM_PKA_STRONGEST_BASIC>
-3.289719332242856

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
73.99970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-catechol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037953
     RDKit          3D
(-)-Catechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4015    2.6921   -1.2885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.6179   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.3705   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -0.7133   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477   -1.9291   -0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.5520    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657    0.7166    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483    1.7795   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    0.9076    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -0.1218    0.9542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7628    0.2598    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847    1.5100    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.8957    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    1.0352   -0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171    1.4485   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.2142   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5094   -1.1030   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5965   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959   -1.4026    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6412   -2.5113    0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -1.6054    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644    2.9199   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3243    0.2431   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891   -2.7168    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    2.7647   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -0.2300    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7238    2.1917    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    2.8741    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233    0.7799   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1151   -2.0170   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761   -1.5794   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -1.4269   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -3.3423    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -1.3201    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.6249    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8668.6828664.002   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8663.3518662.452   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8660.6798667.100   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.0248670.956   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.6928669.410   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.3518667.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.0178666.319   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0178664.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3518664.009   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8671.3538668.640   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.0208669.410   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.6868668.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.6868667.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.0208666.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.3538667.100   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8666.0168667.089   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8664.6828666.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6828664.779   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0168664.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3508664.779   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3508666.319   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    9                                                            
CONECT    3    7                                                            
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6    7   17                                                       
CONECT    7    6    8    3                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2   18                                                  
CONECT   10   11   15    5                                                  
CONECT   11   10   12    4                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   17   21                                                       
CONECT   17   18   16    6                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21    1                                                  
CONECT   21   20   16   13                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0002780
HETATM    1  O1  UNL     1       3.971   3.327  -1.277  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.407   2.080  -1.027  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.178   1.089  -0.475  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.662  -0.186  -0.201  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.477  -1.156   0.355  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.351  -0.495  -0.479  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.573   0.521  -1.042  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.097   1.785  -1.309  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.256   0.212  -1.322  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.449  -0.892  -0.844  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.810  -0.445  -0.420  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.936  -1.156  -0.759  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.206  -0.738  -0.362  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.337   0.418   0.388  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.589   0.871   0.806  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.213   1.131   0.729  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.313   2.288   1.477  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.969   0.701   0.328  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.300  -1.509   0.314  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.321  -2.673   0.749  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.710  -1.801  -0.227  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.419   4.075  -1.686  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.215   1.280  -0.238  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.187  -2.083   0.575  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.461   2.546  -1.746  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.534  -1.689  -1.621  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.874  -2.062  -1.343  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.080  -1.312  -0.639  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.429   0.365   0.568  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.497   2.824   1.736  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.062   1.247   0.583  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.426  -0.754   1.106  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.155  -2.997   1.551  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.531  -2.360  -1.187  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.245  -2.452   0.471  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3    8
CONECT    3    4   23
CONECT    4    5    6    6
CONECT    5   24
CONECT    6    7   21
CONECT    7    8    8    9
CONECT    8   25
CONECT    9   10
CONECT   10   11   19   26
CONECT   11   12   12   18
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   31
CONECT   19   20   21   32
CONECT   20   33
CONECT   21   34   35
END

HMDB0037953
     RDKit          3D
(-)-Catechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4015    2.6921   -1.2885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.6179   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.3705   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -0.7133   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477   -1.9291   -0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.5520    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657    0.7166    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483    1.7795   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    0.9076    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289   -0.1218    0.9542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7628    0.2598    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847    1.5100    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    1.8957    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    1.0352   -0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171    1.4485   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.2142   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5094   -1.1030   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5965   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0959   -1.4026    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6412   -2.5113    0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -1.6054    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644    2.9199   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3243    0.2431   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891   -2.7168    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    2.7647   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -0.2300    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7238    2.1917    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    2.8741    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233    0.7799   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1151   -2.0170   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761   -1.5794   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -1.4269   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -3.3423    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -1.3201    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.6249    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

Synonyms

Value	Source
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol	ChEBI
(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol	ChEBI
(+)-Catechol	ChEBI
(+)-Cyanidan-3-ol	ChEBI
(2R,3S)-(+)-Catechin	ChEBI
(2R,3S)-Catechin	ChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol	ChEBI
Catechuic acid	ChEBI
Cianidanol	ChEBI
Cyanidanol	ChEBI
D-Catechin	ChEBI
Catechuate	Generator
(+)-Catechin	HMDB, MeSH
(+)-Catechin hydrate	HMDB
(+)-Cyanidanol	HMDB, MeSH
(+/-)-catechin	HMDB
(+/-)-catechin hydrate	HMDB
3,3',4',5,7-Flavanpentol	HMDB, MeSH
Biocatechin	HMDB
Catechinate	HMDB
Catechinic acid	HMDB, MeSH
Catergen	HMDB, MeSH
Cianidanolum	HMDB
Cianidol	HMDB
D-(+)-Catechin	HMDB
trans3,3,4,5,7 Pentahydroxyflavane	HMDB
YK-85 light yellow powder 85	HMDB
Acid, catechinic	MeSH, HMDB
KB-53	MeSH, HMDB
Zyma	MeSH, HMDB
Cyanidanol 3	MeSH, HMDB
Cyanidanol-3	MeSH, HMDB
KB 53	MeSH, HMDB
Acid, catechuic	MeSH, HMDB
(+)-Cyanidanol-3	MeSH, HMDB
Epicatechin	MeSH, HMDB
Catechin	MeSH
(-)-Epicatechin	MeSH, HMDB
(+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol	PhytoBank
(+)-(2R:3S)-5,7,3’,4’-Tetrahydroxyflavan-3-ol	PhytoBank
(+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-ol	PhytoBank
(+)-Cianidanol	PhytoBank
3-Cyanidanol, (+)-	PhytoBank
Cyanidol	PhytoBank
Dexcyanidanol	PhytoBank
trans-(+)-3,3',4',5,7-Flavanpentol	PhytoBank
trans-(+)-3,3’,4’,5,7-Flavanpentol	PhytoBank

Molecular Formula

C₁₅H₁₄O₆

Average Mass

290.2681

Monoisotopic Mass

290.07903818

IUPAC Name

(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(+)-catechol

CAS Registry Number

154-23-4

SMILES

O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

InChI Key

PFTAWBLQPZVEMU-DZGCQCFKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:15600 )
Flavans, Flavanols and Leucoanthocyanidins (C06562 )
Flavan 3-ols (C06562 )
Condensed tannins (Proanthocyanidins) (C06562 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020001 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	3	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

Cytoplasm
Extracellular

Biospecimen Locations

Bladder
Blood
Feces
Fibroblasts
Intestine
Platelet
Urine

Tissue Locations

Bladder
Fibroblasts
Intestine
Platelet

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

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	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

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.00667		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	0.0058	0.011	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12650759
Human Urine	Detected and Quantified	0.0125	0.0110	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.650	0.009	uM	Adult (>18 years old)	Female	Normal	HMDB	12494303
Human Blood	Detected and Quantified	1.223	0.147	uM	Adult (>18 years old)	Female	Normal	HMDB	12494303
Human Bladder	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002780

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Catechin

METLIN ID

3419

PubChem Compound

9064

PDB ID

Not Available

ChEBI ID

15600

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tsuchiya H, Sato M, Kato H, Okubo T, Juneja LR, Kim M: Simultaneous determination of catechins in human saliva by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):253-8. doi: 10.1016/s0378-4347(97)00412-x. [PubMed:9448083 ]
Yang CS, Lee MJ, Chen L: Human salivary tea catechin levels and catechin esterase activities: implication in human cancer prevention studies. Cancer Epidemiol Biomarkers Prev. 1999 Jan;8(1):83-9. [PubMed:9950244 ]
Lotito SB, Fraga CG: (+)-Catechin as antioxidant: mechanisms preventing human plasma oxidation and activity in red wines. Biofactors. 1999;10(2-3):125-30. doi: 10.1002/biof.5520100207. [PubMed:10609873 ]
Li C, Lee MJ, Sheng S, Meng X, Prabhu S, Winnik B, Huang B, Chung JY, Yan S, Ho CT, Yang CS: Structural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion. Chem Res Toxicol. 2000 Mar;13(3):177-84. doi: 10.1021/tx9901837. [PubMed:10725114 ]
Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. doi: 10.1080/07315724.2001.10719181. [PubMed:11603654 ]
DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. doi: 10.1093/jn/132.2.172. [PubMed:11823574 ]
Lhoste EF, Ouriet V, Bruel S, Flinois JP, Brezillon C, Magdalou J, Cheze C, Nugon-Baudon L: The human colonic microflora influences the alterations of xenobiotic-metabolizing enzymes by catechins in male F344 rats. Food Chem Toxicol. 2003 May;41(5):695-702. doi: 10.1016/s0278-6915(03)00010-3. [PubMed:12659723 ]
Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ: Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr. 2003 Jun;77(6):1466-73. doi: 10.1093/ajcn/77.6.1466. [PubMed:12791625 ]
Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003 May;67(5):1140-3. doi: 10.1271/bbb.67.1140. [PubMed:12834296 ]
Farivar-Mohseni H, Kandzari SJ, Zaslau S, Riggs DR, Jackson BJ, McFadden DW: Synergistic effects of Cox-1 and -2 inhibition on bladder and prostate cancer in vitro. Am J Surg. 2004 Nov;188(5):505-10. doi: 10.1016/j.amjsurg.2004.07.025. [PubMed:15546559 ]
Lotito SB, Fraga CG: Ascorbate protects (+)-catechin from oxidation both in a pure chemical system and human plasma. Biol Res. 2000;33(2):151-7. doi: 10.4067/s0716-97602000000200015. [PubMed:15693282 ]
Filipe P, Silva JN, Haigle J, Freitas JP, Fernandes A, Santus R, Morliere P: Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic. Photochem Photobiol Sci. 2005 May;4(5):420-8. doi: 10.1039/b416811a. Epub 2005 Apr 5. [PubMed:15875075 ]
Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. doi: 10.1079/bjn20051522. [PubMed:16197573 ]
Roura E, Andres-Lacueva C, Estruch R, Lamuela-Raventos RM: Total polyphenol intake estimated by a modified Folin-Ciocalteu assay of urine. Clin Chem. 2006 Apr;52(4):749-52. doi: 10.1373/clinchem.2005.063628. Epub 2006 Feb 9. [PubMed:16469857 ]
Pignatelli P, Di Santo S, Buchetti B, Sanguigni V, Brunelli A, Violi F: Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006 Jun;20(8):1082-9. doi: 10.1096/fj.05-5269com. [PubMed:16770007 ]

Showing metabocard for Catechin (MMDBc0033606)

MOL for #<Metabolite:0x00007f923434c3a8>

3D MOL for #<Metabolite:0x00007f923434c3a8>

3D SDF for #<Metabolite:0x00007f923434c3a8>

3D-SDF for #<Metabolite:0x00007f923434c3a8>

PDB for #<Metabolite:0x00007f923434c3a8>

3D PDB for #<Metabolite:0x00007f923434c3a8>

SMILES for #<Metabolite:0x00007f923434c3a8>

INCHI for #<Metabolite:0x00007f923434c3a8>

Structure for #<Metabolite:0x00007f923434c3a8>

3D Structure for #<Metabolite:0x00007f923434c3a8>