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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:13:26 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037955

Secondary Accession Numbers

HMDB37955

Metabolite Identification

Common Name

(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin

Description

(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 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 (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin has been detected, but not quantified in, chinese cinnamons (Cinnamomum aromaticum) and herbs and spices. This could make (±)-3',4'-methylenedioxy-5,7-dimethylepicatechin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin.

Structure

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

HMDB0037955
     RDKit          3D
(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.1549    4.1609   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666    2.9148   -0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830    1.7119   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.5486   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -0.6918   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702   -1.8258    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574   -1.7963    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.7461   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.3818   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    1.5956   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    0.2319   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -0.9963   -0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -0.7136   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -1.4963    0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614   -1.2402    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -0.1606    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    0.6464   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    0.3501   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    1.6555   -0.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2988    1.6829    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    0.3850    0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814   -1.9735    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -3.2995    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -2.0507   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    4.8417   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283    4.1305   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157    4.6206    0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.6215   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896   -1.3819    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8284   -2.7733    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825   -1.1287   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    2.4933   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938   -1.3444   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -2.3278    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -1.8648    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    0.9975   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506    2.3988    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2453    1.8898   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.6909    1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -3.4805   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101   -2.6629    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -2.6132   -1.1303 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 22 24  1  0
 10  3  1  0
 18 13  1  0
 24  8  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

  Mrv0541 05061310072D          

 24 27  0  0  0  0            999 V2000
    7.0714    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    4.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  2  0  0  0  0
 16  7  2  0  0  0  0
 16 12  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  2  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037955

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-20-11-6-15(21-2)12-8-13(19)18(24-16(12)7-11)10-3-4-14-17(5-10)23-9-22-14/h3-7,13,18-19H,8-9H2,1-2H3

> <INCHI_KEY>
MMKQEVQTCAAXTI-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.96530531278701

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.3172592383333335

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.867563940924796

> <JCHEM_PKA_STRONGEST_BASIC>
-3.294127532239494

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
84.7694

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037955
     RDKit          3D
(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.1549    4.1609   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666    2.9148   -0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830    1.7119   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.5486   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -0.6918   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702   -1.8258    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574   -1.7963    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.7461   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.3818   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    1.5956   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    0.2319   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -0.9963   -0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -0.7136   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -1.4963    0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614   -1.2402    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -0.1606    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    0.6464   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    0.3501   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    1.6555   -0.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2988    1.6829    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    0.3850    0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814   -1.9735    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -3.2995    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -2.0507   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    4.8417   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283    4.1305   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157    4.6206    0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.6215   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896   -1.3819    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8284   -2.7733    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825   -1.1287   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    2.4933   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938   -1.3444   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -2.3278    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -1.8648    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    0.9975   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506    2.3988    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2453    1.8898   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.6909    1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -3.4805   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101   -2.6629    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -2.6132   -1.1303 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 22 24  1  0
 10  3  1  0
 18 13  1  0
 24  8  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.200   5.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   9.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.532   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.199   6.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173   7.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.532   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.199   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.864   3.613   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.866   6.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.199   2.073   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.268   8.709   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.268   6.217   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.531   6.693   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   10                                                       
CONECT    4    3   14                                                       
CONECT    5   10   17                                                       
CONECT    6   11   15                                                       
CONECT    7   11   16                                                       
CONECT    8   12   13                                                       
CONECT    9   22   23                                                       
CONECT   10    3    5   18                                                  
CONECT   11    6    7   20                                                  
CONECT   12    8   15   16                                                  
CONECT   13    8   18   19                                                  
CONECT   14    4   17   22                                                  
CONECT   15    6   12   21                                                  
CONECT   16    7   12   24                                                  
CONECT   17    5   14   23                                                  
CONECT   18   10   13   24                                                  
CONECT   19   13                                                            
CONECT   20    1   11                                                       
CONECT   21    2   15                                                       
CONECT   22    9   14                                                       
CONECT   23    9   17                                                       
CONECT   24   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0037955
HETATM    1  C1  UNL     1      -3.155   4.161  -0.523  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.767   2.915  -0.348  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.083   1.712  -0.312  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.804   0.549  -0.133  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.194  -0.692  -0.086  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.970  -1.826   0.096  1.00  0.00           O  
HETATM    7  C5  UNL     1      -5.357  -1.796   0.238  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.832  -0.746  -0.223  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.060   0.382  -0.404  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.717   1.596  -0.444  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.289   0.232  -0.532  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.997  -0.996  -0.571  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.374  -0.714  -0.198  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.038  -1.496   0.704  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.361  -1.240   1.072  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.005  -0.161   0.499  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.363   0.646  -0.413  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.060   0.350  -0.741  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.224   1.656  -0.837  1.00  0.00           O  
HETATM   20  C16 UNL     1       6.299   1.683   0.054  1.00  0.00           C  
HETATM   21  O5  UNL     1       6.287   0.385   0.621  1.00  0.00           O  
HETATM   22  C17 UNL     1       0.281  -1.973   0.292  1.00  0.00           C  
HETATM   23  O6  UNL     1       0.737  -3.300   0.085  1.00  0.00           O  
HETATM   24  C18 UNL     1      -1.174  -2.051  -0.176  1.00  0.00           C  
HETATM   25  H1  UNL     1      -3.924   4.842  -0.976  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.328   4.131  -1.276  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.816   4.621   0.423  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.873   0.622  -0.028  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.690  -1.382   1.213  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.828  -2.773   0.109  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.782  -1.129  -0.544  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.141   2.493  -0.584  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.894  -1.344  -1.635  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.546  -2.328   1.150  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.880  -1.865   1.788  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.554   0.997  -1.469  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.151   2.399   0.898  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.245   1.890  -0.488  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.301  -1.691   1.345  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.579  -3.480  -0.885  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.710  -2.663   0.602  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.259  -2.613  -1.130  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   28
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   29   30   31
CONECT    8    9   24
CONECT    9   10   10   11
CONECT   10   32
CONECT   11   12
CONECT   12   13   22   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   18   36
CONECT   19   20
CONECT   20   21   37   38
CONECT   22   23   24   39
CONECT   23   40
CONECT   24   41   42
END

HMDB0037955
     RDKit          3D
(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.1549    4.1609   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666    2.9148   -0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830    1.7119   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.5486   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -0.6918   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702   -1.8258    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574   -1.7963    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.7461   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.3818   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    1.5956   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    0.2319   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -0.9963   -0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -0.7136   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -1.4963    0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614   -1.2402    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -0.1606    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    0.6464   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    0.3501   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    1.6555   -0.8374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2988    1.6829    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    0.3850    0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814   -1.9735    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -3.2995    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -2.0507   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    4.8417   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283    4.1305   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157    4.6206    0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.6215   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896   -1.3819    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8284   -2.7733    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825   -1.1287   -0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    2.4933   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938   -1.3444   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -2.3278    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -1.8648    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    0.9975   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506    2.3988    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2453    1.8898   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.6909    1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -3.4805   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101   -2.6629    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -2.6132   -1.1303 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 22 24  1  0
 10  3  1  0
 18 13  1  0
 24  8  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3',4'-Methylenedioxy epicatechin 5,7-dimethyl ether	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

Traditional Name

2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

CAS Registry Number

87562-72-9

SMILES

COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C18H18O6/c1-20-11-6-15(21-2)12-8-13(19)18(24-16(12)7-11)10-3-4-14-17(5-10)23-9-22-14/h3-7,13,18-19H,8-9H2,1-2H3

InChI Key

MMKQEVQTCAAXTI-UHFFFAOYSA-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
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
3-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Secondary alcohol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037955)
Cytoplasm (HMDB: HMDB0037955)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037955)

Source

Exogenous

Exogenous (HMDB: HMDB0037955)

Food

Food (HMDB: HMDB0037955)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037955)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037955)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162 - 164 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.32	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.77 m³·mol⁻¹	ChemAxon
Polarizability	33.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.211	31661259
DarkChem	[M-H]-	176.99	31661259
DeepCCS	[M+H]+	177.486	30932474
DeepCCS	[M-H]-	175.128	30932474
DeepCCS	[M-2H]-	209.219	30932474
DeepCCS	[M+Na]+	184.987	30932474
AllCCS	[M+H]+	178.9	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	182.0	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	181.9	32859911
AllCCS	[M+Na-2H]-	181.5	32859911
AllCCS	[M+HCOO]-	181.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-3',4'-Methylenedioxy-5,7-dimethylepicatechin	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1	3994.9	Standard polar	33892256
(??)-3',4'-Methylenedioxy-5,7-dimethylepicatechin	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1	2711.9	Standard non polar	33892256
(??)-3',4'-Methylenedioxy-5,7-dimethylepicatechin	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1	2917.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-3',4'-Methylenedioxy-5,7-dimethylepicatechin,1TMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C)C(C3=CC=C4OCOC4=C3)OC2=C1	2838.1	Semi standard non polar	33892256
(??)-3',4'-Methylenedioxy-5,7-dimethylepicatechin,1TBDMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C(C)(C)C)C(C3=CC=C4OCOC4=C3)OC2=C1	3093.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wmr-0938000000-5468ff40061503bad51a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin GC-MS (1 TMS) - 70eV, Positive	splash10-0079-6209000000-5f0c83745d63bbe18004	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 10V, Positive-QTOF	splash10-001i-0319000000-121b6cc518c4b96ee61d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 20V, Positive-QTOF	splash10-014i-0912000000-3ad8568c3df9e2d3b2e6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 40V, Positive-QTOF	splash10-0f79-1930000000-28431dd5924e742350ad	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 10V, Negative-QTOF	splash10-004i-0119000000-41fbe2446264fcb7fdbb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 20V, Negative-QTOF	splash10-0400-0924000000-1ab90f749d28732d3aad	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 40V, Negative-QTOF	splash10-0079-2910000000-efc32488c35eeee88117	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 10V, Negative-QTOF	splash10-004i-0009000000-4ca52439b731e1c3fd61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 20V, Negative-QTOF	splash10-01ta-0269000000-656500212d771efc7e8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 40V, Negative-QTOF	splash10-01q1-1291000000-ae986023a6a433789bfc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 10V, Positive-QTOF	splash10-001i-0009000000-3b03c1331c05e6f857d3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 20V, Positive-QTOF	splash10-001i-0908000000-ab3d3a34a917d2d47af3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 40V, Positive-QTOF	splash10-00kr-1931000000-358545b4e78aeba1c6b9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017127

KNApSAcK ID

C00008829

Chemspider ID

29365110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71307295

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin (HMDB0037955)

MOL for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D MOL for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D SDF for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D-SDF for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

PDB for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D PDB for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

SMILES for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

INCHI for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

Structure for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D Structure for HMDB0037955 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra